how-to-buy-your-first-suit-shoppingFor most young guys setting out to look sharp, figuring out exactly how to buy your first suit can be a little overwhelming.

There’s a seemingly endless array of options available, to say nothing of all the questions to ask and decisions you have to make.

And much like one of life’s other memorable firsts, it can be easy for guys to overthink it and put way too much pressure on themselves — after all, you never forget your first time suit.

But unlike that other pursuit, buying your first suit is one endeavor in which extensive – ahem – “internet research” can actually make you look like a pro your very first time.

In this post I’ll lay out everything you need to know about how to buy your first suit and outline 10 straightforward steps you can follow to find the perfect kit to fit your body, budget and style.

how-to-buy-your-first-suit-intro3By the end of this post you’ll know:
  • What to look for in your first suit
  • How much you need to spend
  • Where to get it
  • How to make sure it fits like a glove
  • How to make yourself and your new suit stand out from the crowd

So with the foreplay (and this terrible sex metaphor) officially over, let’s dive in and unpack exactly how to buy your first suit.

Note:

If you’d prefer to skip the deep dive and just get the 10-Step Checklist, click here.

How to buy your first suit

How to Buy Your First Suit

10   Steps   For   Suiting   Up   in   Style

Step 1: Define its Purpose

how-to-buy-your-first-suit-bondBefore you can even start to think about what to buy, make sure you’ve defined why you’re buying it in the first place.

Answering a few simple questions about your suit now, before the process has even started, will ensure you buy the one that suits your needs. (Yes, that was a suit pun. And yes, I am the worst.)

A few key questions to ask yourself include:

  • Do you want to wear it year-round, or just during one season (i.e. only during summer or only during winter)?
  • Are you mostly wearing it to weddings and other social functions, or for work/business?
  • Do you expect to wear it once or twice a year, or more like once or twice a week?
  • Do you plan to wear the pieces separately (i.e. wear the jacket as a blazer or wear the pants without it)?

Jot your answers down in order to really entrench them in your mind and keep yourself laser-focused on what you need.

Depending on where you go to buy a suit (much more on that below) you may find that salespeople try to push you in one direction or another. Having a clear idea of exactly what you want will make you less likely to be led astray by a sales clerk who’s more concerned with making a sale than meeting your needs.

how-to-buy-your-first-suit-stylish
For your first suit, you probably want something versatile that you can wear on any occasion.

Stylish, Versatile, Affordable

Since you’re obviously wondering how to buy your first suit, I’m going to assume that you have a lot in common with most first-time suit buyers.

Which means you probably…

  • Want a suit you can wear year-round
  • Want something you can wear to both social and business functions
  • Expect it to wear it roughly six times a year (for weddings, job interviews, funerals, etc.)
  • Might need to wear it more often (depending on your job)
  • Might want to wear the pieces separately

The rest of this post will be geared toward these assumptions, but if your needs differ significantly, feel free to email me with any specific questions.

Your Move:

Opt for a good, multi-purpose suit that you can wear year-round to any occasion that calls for something a little spiffier than a blazer.
How to buy your first suit

Step 2: Set a Budget

How much are you willing to spend?

how-to-buy-your-first-suit-budgetAs noted philosopher Kanye West once so gloriously tweeted, “Suits is an expensive addiction.”

Buying a suit is not unlike other, more grammatically correct addictions: when getting your first fix you can either opt for the lower-end cheap stuff, the most prime product, or something in between. It all depends on your personal preference.

And your budget.

Price ≠ Quality

When learning how to buy your first suit, one of the biggest early hurdles is figuring out exactly how much you need to drop. It’s important to remember that the most expensive suits are not necessarily the best.

There are lots of other factors that better indicate a suit’s quality.

how-to-buy-your-first-suit-material
How does your suit fit? What material is it made of? These things matter as much as (if not more than) price.

Things to Consider:

  • Fit (much more on that below)
  • Material
    • Is it lightweight, heavy or in between?
    • Is it shiny or matte?
    • Does it look cheap?
    • Does it feel like cloth, or like it has some kind of light plastic coating?
  • Craftsmanship
  • Style
    • Does it have notched or peak lapels? And how wide are they?
    • Does it have an extra ticket pocket?
    • Does it look classic and evergreen, or modern and trendy?

Fortunately, thanks to the explosion of the menswear industry over the past few years, there are now more options than ever for a suit that meets all of your criteria without breaking the bank.

how-to-buy-your-first-suit-cheap
Cheap suits can look good in photos – but not so much in real life. (Especially if they’re falling apart.)

A Word of Warning:

Don’t Go Too Cheap

It’s definitely possible to get a well made, good-quality suit for a few hundred bucks, but I’d be very wary of any suit priced at less than $100.

Better to invest a couple hundred now in a suit you can wear for years to come than to spend a quick hundred on a piece of crap that’s going to rip, wrinkle or go out of style in the next 12 months.

For your first suit, I’d recommend something in the $300 to $500 range.

Even at the low end of this range, you should be able to find a suit that you can wear for years (and maybe even decades), without having to choose between suiting up or paying your rent.

Your Move:

Spend at least $300 (but probably no more than $500) for a well-made and well-fitting suit that will last.

how-to-buy-your-first-suit-pdf-ad2 How to buy your first suit

Step 3: Get Measured

how-to-buy-your-first-suit-measuredI alluded to this above, but it’s worth repeating.

No matter what budget you’ve set for yourself, there’s one factor – above all others – that determines how good a suit looks:

How it fits.

I’ve seen very rich men wear very expensive suits that look like total crap.

And I’ve seen fiscally challenged men wear inexpensive suits that make them look like f@¢&ing movie stars.

With suits, as with all clothing, fit trumps price. So before you decide which suit to buy, you want to make sure you’ve got an accurate set of measurements to work from.

There are two ways to find your measurements.

1. Go to a Tailor

By far the best and most accurate way to get measured for a suit is to simply head into any tailor or suit store and ask to get measured up.

how-to-buy-your-first-suit-wikihow
Wikihow has a step-by-step guide for measuring yourself for a suit.

Tailors will know exactly which measurements to take and how to do so accurately.

2. Do it Yourself

It’s a little tricky, but if you’ve got a measuring tape, it can be done. Wikihow has a great little tutorial, complete with illustrations, laying out exactly how to do it.

Your Move:

Either take your own suit measurements or have a tailor do it for you.
How to buy your first suit

Step 4: Picky Any Color You Want

(As long as that color is navy blue)

how-to-buy-your-first-suit-navyThis may be the most controversial thing I say in this entire post:

Your first suit should absolutely be navy blue.

I know, I know. There are dozens if not hundreds of other perfectly viable colors out there. And yes, I’ve heard all the arguments in favor of grey, that other stalwart of a man’s wardrobe.

But for your first suit, there’s simply no more classic, versatile or sophisticated choice than navy.

how-to-buy-your-first-suit-navy-full-3Classic:

Color trends come and go pretty quickly in the fashion world, but navy blue is always in style, always masculine, and it works with any complexion.

Versatile:

A navy suit looks sharp in literally any setting, from weddings and funerals to job interviews and corporate functions.

Sophisticated:

James Bond wears navy suits. Need I say more? (Come to think of it, I probably should have led with that.)

In addition to all of that, the dark hue is much more forgiving when it comes to stains, dirt or other grime, meaning that you can wear the hell out of it and not feel like you need to run to the dry cleaner after every wear.

Hopefully I’ve convinced you that navy is definitely the way to go for your first suit, but if for some reason you’re still entertaining other colors, I certainly won’t judge you. (Unless you go with black.)

Your Move:

For your first suit, go with navy blue.
How to buy your first suit

Step 5: Choose Between Custom Made or Off-the-Rack

how-to-buy-your-first-suit-rackSince choosing the color is really no choice at all, this is where you’re going to have to make your first real decision: do you want to buy a suit off the rack or have one custom made just for you?

Let’s define each option and then break down the pros and cons.

Off-the-Rack

What is an Off-the-Rack suit?

An off-the-rack suit is one that you literally take off a rack in a clothing store (or order online).

How does it work?

It’s pre-made according to standard suit sizes, which use your chest size as a rough approximation for the size of your body. The chart below from suitupp.com outlines each standard size.

how-to-buy-your-first-suit-suit-size-chart

So if you’re trying to decide which off-the-rack suit to try on, you’d take a look at the measurements you (or your tailor) took earlier.

If your chest size says 40, you’d go for a 40 suit in one of the three fit options.

If you’re shorter than 5’6” you’ll want a 40-short, or 40S. If you’re 5’7” to 5’11” you’ll want a 40-regular, or 40R.

And if you’re 6’ or up you’ll want a 40-long, or 40L. (Sidebar: Why isn’t that last size just called “tall”?)

Pros:
  • Price
    • Off-the-rack suits are generally a much more affordable option when compared with custom made ones, which are usually more expensive.
  • how-to-buy-your-first-suit-rack-of-suitsAvailability
    • It’s easy to find an off-the-rack suit. The menswear department at any department store will be packed full of ‘em, as will stores you can find in any mall like Banana Republic and J.Crew.
Cons:
  • Imprecise Fit
    • It’s very rare to find an off-the-rack suit that fits like a glove. Instead, what’s more likely to happen is that you’ll find a suit that fits you in the chest and shoulders, but is a little bit off in terms of sleeve length, waist size or pants. If you choose the right size off-the-rack, a good tailor should be able to make some tweaks so that it fits you (almost) perfectly, but you’ll have to factor that cost into the overall price of the suit.
  • Quality
    • Don’t get me wrong: many off-the-rack suits are exceptionally well made. But because they’re often mass-produced, some are going to be cheaply assembled. If you decide to opt for something off-the-rack, choosing the right brand will be crucial (more on that later).
  • Generic Styling
    • Because you’re choosing a suit that’s already been manufactured, you have no control or input into details like the color, material, lapel style, button stance, etc. All you can do is sift through the racks to find one that you like. (But to be fair, there are so many options out there that this usually isn’t a problem.)

Custom Made

how-to-buy-your-first-suit-bespokeWhat is a custom made suit?

A custom made suit (also called a Bespoke or Made to Measure suit) is exactly what its name implies: a suit custom made just for you, to your exact specifications and preferences.

How does it work?

You visit a suit maker, who measures you even more thoroughly than your tailor would. They’ll ask you questions about every facet of the suit’s style and fit: what kind of lapels do you want? What kind of fabric? How many pockets? How long do you want the jacket? And so on.

They then go off and cut the fabric of your choice into a pattern tailored just for you. The end result is a one-of-a-kind suit that’s specifically made to fit you perfectly.

how-to-buy-your-first-suit-harvey-specter
Harvey Specter wears custom made suits. (Though it should be noted that in addition to being fictional, he’s also rich as shit.)
Pros:
  • Perfect Fit (obviously)
    • There are other reasons to get a custom suit, but this is the main one. A man never looks better than when he’s decked out in a custom kit made just for him.
  • Quality
    • Custom suits are usually made with high-quality fabrics and a great attention to detail. As a result, they not only look great on their intended wearer, but can last a lifetime if properly cared for.
  • It’s Classy as Shit.
    • People who have custom suits made include Steve McQueen, James Bond and Harvey Specter. And yes, two of those people are fictional. But they could both kick my candy ass – and look dapper as shit while they’re at it.
Cons:
  • Price
    • To paraphrase an old adage: there’s always a catch – and the catch is usually money. A custom suit will fit you perfectly and meet all of your criteria for the perfect suit, but you’ll pay for the pleasure.
  • Scarcity of Sources
    • While it’s easy to wander into a mall and find a ton of great off-the-rack options, it’s a lot harder to find a good suit maker who will craft something custom for you. But, harder doesn’t mean impossible. Brands like Indochino (more on them below) have popped up over the past few years to make custom suits more widely available.

Your Move:

(aka The Verdict: Custom or Off-the-Rack?)

For your first suit, I’d definitely recommend going off-the-rack.

As mentioned, you can easily find plenty of stylish and well made options, then have a tailor tweak it so it almost looks like it was custom made for you – all for a hell of a lot less money than you would drop by going custom.

How to buy your first suit

Step 6: Choose a Store/Brand

how-to-buy-your-first-suit-retailersAs I mentioned earlier, the world of menswear has exploded over the past few years.

So if you’re wondering not just how to buy your first suit, but where, the good news is you have a ton of options to choose from.

The bad news is you have a ton of options to choose from.

After all, some psychologists have argued that increased consumer choice can lead to anxiety and paralysis by analysis.

Suiting up should be fun, not nauseating. So to make your decision more manageable, let’s review a few of the most popular stores and brands that sell stylish, well made and (mostly) affordable suits.

how-to-buy-your-first-suit-jcrew-ludlow
The J.Crew Ludlow

J.Crew

For most guys looking to buy their first suit, I highly recommend J.Crew. Their off-the-rack suits come in two main fits, which they call their Ludlow and Crosby lines.

They’ve had their Ludlow line for years, and it’s become a staple for guys looking for a sleek, modern and crisp-fitting suit that doesn’t break the bank.

Their newly added Crosby line is similar, but is specifically made with a little more room to accommodate guys who have been sticking to their workout plan. (If you’re not sure which line is right for you, Dappered has a great summary of the differences here.)

Both lines are well made from fabrics that look and feel like they should cost twice what they do, which make them an obvious and excellent choice for your first suit.

how-to-buy-your-first-suit-jcrew-factory-thompson
J.Crew Factory Thompson

J.Crew Factory

Think of J.Crew Factory has J.Crew’s kid brother: it’s got many of the same sensibilities, but not quite the same level of refinement (or budget).

At J.Crew Factory you’ll find the Thompson line, which is similar to the Ludlow in style but lacks the quality that really sets J.Crew’s main line apart. The boys over at the subreddit r/malefashionadvice have summed up many of the differences between the Ludlow and the Thompson here.

Personally I’ve tried on a few different Thompson suits and found them a bit uninspiring. While a 40S in the Ludlow fit me like a glove and cut a striking profile right off the rack, the Thompson in a 40S ran considerably bulkier, so my tailor would have to work a bit of magic to get the slimmer profile I’d prefer.

With that said, it’s probably doable for the tailor, so if you’re not too picky about fabric and you’re on a stricter budget, the Thompson is a perfectly legitimate option.

how-to-buy-your-first-suit-br-standard
Banana Republic Standard Fit

Banana Republic

Like J.Crew, Banana Republic (BR) has a pretty wide selection of suits that cut a trim and modern profile, and have the advantage of being easily found in almost any mall.

They also offer two main fits, but avoid J.Crew’s penchant for cute names: BR just calls them the Slim Fit and the Standard Fit, which is pretty self explanatory.

For the first time suit-buyer, the difference between a J.Crew suit and a BR option is going to be pretty minimal.

I find that the shoulders on BR’s suits have a little more padding, as opposed to J.Crew, which is more natural. Which you prefer will depend on your build and personal preference.

In general, both are fine options, and you should spend some time trying on suits in both stores.

Suitsupply

how-to-buy-your-first-suit-suitsupply-napoliMoving out of the mall, Suitsupply is a more recent addition to the North American market that sells suits both online and in a few select stores across the continent.

Unlike J.Crew and BR, which only offer two basic choices in style, Suitsupply offers 13 (each with a fancy sounding Italian name), which can be a little overwhelming for first-time suit buyers.

Another downside with them is that their suits are not sold in separates. Suit separates means you can choose whatever size jacket you want, then also choose a matching pair of pants in whatever size you want.

You might say it’s a system that makes total sense, which is why you’ll find it being offered by most modern suit vendors, including J.Crew and BR.

But Suitsupply is old school. They sell one jacket and one corresponding pair of pants together, and mixing/matching is verboden. So if you take a 40 jacket but would rather have a 34 waist instead of the 32 waist that comes with it, you may be out of luck.

One thing they do have working in their favor is an excellent staff who really know their stuff. At Suitsupply, selling suits is literally all they do, and they’re definitely experts.

As a first-time suit buyer, you could probably just explain that you want a good all-purpose navy suit you can wear year-round and trust that you’re in good hands. (For a little more context, check out Dappered’s review of the entire Suitsupply experience.)

But you’ll have to be able to find them in order to do that, and unfortunately their coverage isn’t very broad. They have 11 stores in the US with five more on the way, along with one here in Toronto and another one coming to Montreal.

Even though the pre-determined pant size thing is a bit of a bummer, if you happen to live in close proximity to one of their stores then I would still definitely recommend them.

Other Options:

how-to-buy-your-first-suit-indochino-essential-navy
Indochino Essential Navy
Indochino

They actually make custom suits, so their prices can run pretty steep. (To learn more about Indochino’s made-to-measure process, check out this review from friend of the blog Brock McGoff over at The Modest Man.)

Pop into any of their 10 North American locations, get measured, choose your fabric and details, and they’ll make something to your specs.

Unfortunately, their showrooms are clustered along the east and west coasts, so if you’re in the heartland you’re out of luck.

Department Stores

You can still do what our fathers did, which is head down to the menswear section of your nearest department store.

You’ll find some decent options there, but more often than not they’ll be priced somewhat exorbitantly, and potentially be less modern than you’re looking for. Proceed with caution.

Discount Department Stores

There are diamonds to be found in the rough at places like Nordstrom Rack, Marshall’s, TJ Maxx and the like – but there is a lot of rough. It’s probably not worth wasting your time sifting through the racks if you’re looking for something with both the style and the quality that will let you wear it for years.

Men’s Warehouse

If you’re on a tight budget, you could do worse than Men’s Warehouse (or Moores, as it’s known here in Canada). But it’s pretty easy to do better.

Your Move:

Survey the brands/retailers above and familiarize yourself with the landscape. Check out their websites and narrow down the top three that you think you’d like to try on in person.

how-to-buy-your-first-suit-pdf-ad2 How to buy your first suit

Step 7: Try it On

how-to-buy-your-first-suit-try-it-on-1
“Oh. Hell. Yes. The only thing that looks better than this suit is this dope-ass smirk.” – This Guy

Most of the brands I mentioned above offer e-commerce, but it’s worth emphasizing how important it is to try your suit on in person.

Buying any clothes online is a bit of a gamble. And just as the size of a medium sweater or a size 9 shoe will vary from brand to brand, so will suit sizing.

See It (On You) to Believe It

Don’t think that just because you’ve taken your measurements, you’re safe to order that size 40R Ludlow from J.Crew.

What if you’re actually more of a Crosby fit? Or maybe the Banana Republic or Suitsupply 40R fits closer to your frame? There’s only one way to find out.

I’d recommend trying on at least five different suits before buying your first one, ideally from at least three different brands/stores. It’s easy to look at a model on the J.Crew website and think “I want that,” but how it fits, looks and feels on your body is an entirely different story.

Invest in Yourself
how-to-buy-your-first-suit-try-it-on-2-1
Don’t forget to check the suit from all angles.

Keep in mind that you’re not just buying something, you’re making an investment. You want to buy something you can wear for years to come, so taking the time to do your due diligence now is worthwhile.

Plus, once you’ve surveyed the landscape and have a feel for what you like, buying your second suit becomes a hell of a lot easier.

Love that first blue Napoli suit you bought from Suitsupply? They also make it in multiple shades of gray, any of which might be right for your next kit.

Your Move:

Try on five different suits from three different stores to get a sense of what’s out there, what you like and what looks, fits and feels right on your frame.

How to buy your first suit

Step 8: Pull the Trigger!

how-to-buy-your-first-suit-paymentYou’ve got your measurements, you’ve surveyed the landscape and you’ve even tried on multiple options.

It’s time to pull the trigger and buy your first (motherf@¢&ing!) suit!!

Of course, just because you’ve made the purchase doesn’t mean you’re ready to step out in your suit just yet…

Your Move:

Go for it: purchase your first suit.

How to buy your first suit

Step 9: Get it Tailored

how-to-buy-your-first-suit-step9If you’ve read this far, this one won’t come as much of a surprise.

Assuming you stuck with my advice and bought a suit off the rack, you’ll definitely want to get it tailored.

(If you sprung for a custom made suit than it should fit like a glove by the time you take it out of the store. Congrats! Now move on to step 10 to find out how to make it look even better.)

The exact tailoring your suit needs will obviously depend on you, your body and your new suit, but here are a few of the most common alterations you’ll want to consider.

how-to-buy-your-first-suit-sleeve-length-2Sleeve Length

A perfect fitting suit says, “I’m confident and in command.” A suit with sleeves that are too long says “I borrowed this from my dad.”

When your arms are hanging straight at your sides, you want the suit to reveal about ¼ to ½ an inch of shirt cuff (assuming your shirt fits properly, of course).

Go any shorter than that, and the suit might say, “I borrowed this from my kid brother,” which is also not what you’re going for.

how-to-buy-your-first-suit-sleeve-lengthWARNING:

Do not let your tailor pressure you into leaving the sleeves long. (Actually, don’t let him pressure you into anything.)

Most tailors are from another generation (i.e. old guys) and have very different impressions of how your suit should fit.

Know what you want going in, explain it clearly and have them repeat it back to you. Be polite, but firm. You just dropped half a grand on this thing, and you want to make sure you’re getting the final product you want.

Pant Length

how-to-buy-your-first-suit-pant-lengthAgain, you want to get this right so you neither look like you’re drowning in fabric nor preparing for a (handsome-ass) flood.

If you read GQ or other men’s fashion magazines, you might have noticed that the modern style is to keep the pant legs cropped pretty short and show a lot of sock (or bare ankle, weather permitting).

This looks great on some guys, but it can be a bit tricky to pull off without looking like you spontaneously went through an overnight growth spurt.

If you want to play it a bit more conservative, tell your tailor you want about ¾ of an inch of “break.” The break is the part of your pant leg that crinkles a bit when it touches the top of your shoe.

You definitely don’t want to overdo it, but leaving just a little extra fabric will allow you to cross your legs without treating your wedding date or potential employer to that gnarly scar on your shin.

how-to-buy-your-first-suit-jacket-waist2Jacket Waist/Midsection

You should be able to find a jacket that fits pretty well across the chest and shoulders based on your measurements.

But depending on how trim you are through the middle, you might find that the waist needs to be taken in a little bit.

As a general rule, when the top button of your suit is done up, you want to be able to fit your closed fist between the button and your stomach.

Leave any more room than that and you’ll find that the silhouette of your jacket looks too boxy. Any less and, well…

Pant Waist

how-to-buy-your-first-suit-pants-waistIf you opt for one of the brands above that sells suit separates, you should be able to find a fit off the rack that hugs your hips and butt appropriately.

But occasionally a little nipping and tucking is needed, particularly if you want to go beltless.

And just in case this doesn’t go without saying: it’s easier to take pants that are a little too loose in, than it is to let tight pants out out.

If you’re concerned about having room where it counts, consider sizing up when buying, then have your tailor take them down to a comfortable level. (He can always let them back out again later if you add a little heft.)

Your Move:

Take your new suit to a tailor and have him or her make any necessary adjustments.

How to buy your first suit

Step 10: Accessorize

how-to-buy-your-first-suit-accessoriesOK, so you’ve got a suit that fits like a glove and you’re ready to strike out on the town.

There’s just one problem: you can’t exactly pair your new suit with your Nikes and your gym clothes. (I mean, you could, but… please don’t.)

You’re definitely going to want a shirt and tie, and maybe a few more accessories to take your look to the next level.

One of the many great things about a navy blue suit is that it can be accessorized in about a thousand different ways. But to help get you started, here are a few recommendations that you can combine for an overall look that’s modern, classic and, as they say on London’s Savile Row, classy as shit. (They definitely don’t say that.)

how-to-buy-your-first-suit-shirtShirts

A shirt isn’t really an accessory — it’s a necessity — which also makes it the best place to start.

With a navy blue suit, you really can’t beat a crisp white dress shirt. Other viable options include light blue and a lighter shade of gray.

Where to Get Shirts:

Pretty much all of the brands/stores I recommend above will also sell good quality dress shirts. (My personal go-to is the Banana Republic non-iron shirt pictured here.)

But keep in mind that unlike suits, which can last decades if cared for properly, shirts have a pretty short lifespan.

While you still want something of fairly high quality, shelling out too much for a shirt might not be a great long-term investment.

Ties

how-to-buy-your-first-suit-tiesFew combinations are more powerful than a navy blue suit, a crisp white shirt and a maroon or burgundy tie. (Brown, blue or even black could work well too.)

Unlike shirts, ties can potentially last a lifetime if you treat them well. And while it’s certainly possible to shell out big bucks for expensive fabrics, personally I’ve always found the lower cost options to look just as good — if not better.

Where to Get Ties:

One of the best options you’ll find is The Tie Bar, the online retailer that specializes in low-cost high-awesomeness ties and other accessories.

I’ve also had great luck with Amazon, particularly when ordering knit ties. Which reminds me…

Full Disclosure

Amazon has muscled into the menswear world in a major way, and it’s actually become a great resource for most of the accessories listed here, so I’ve included links where relevant in this section.

But in the interest of full disclosure, you should know that if you decide to click any of the Amazon links below and purchase from them, I’ll get a small commission. Just wanted to be as upfront and transparent about that as possible.

OK, boring transparency out of the way. Moving right along…

Belt/Shoes/Watch

how-to-buy-your-first-suit-belt-shoesIf you remember nothing else about accessories, remember this: your belt and your shoes should always match – or at least be in the same family.

That means a brown belt gets brown shoes, and a black belt gets black shoes.

The same rule applies if you’re wearing a leather watch strap: you’re either going all black or all brown, not mixing it up.

The black shoes/belt/watch combo can work with a navy suit, but since brown and blue are such a killer combination, I recommend sticking with brown.

how-to-buy-your-first-suit-shoesWhere to Get Them:

Shoes are like suits: sizes are supposed to be standard but can vary widely, so you definitely want to try them on in-person before buying.

In addition to the suit stores I recommend above, I also love Johnston & Murphy, and have even had good luck with certain Aldo shoes (though they’re obviously not quite as well made).

Belts on the other hand are actually the perfect thing to buy online because they really do come in standard sizes. Almost all major menswear retailers sell them. And of course, here’s your perfunctory Amazon link, where you’ll find hundreds of options.

Pro Tip:

With belts, the sleeker the better. Thick, chunky belts can look good with jeans and casual looks, but not so much with suits. Look for one about 1 to 1.5 inches wide.

Watches can be found just about anywhere, and you can probably guess where I’d recommend looking online.

Pocket Square

how-to-buy-your-first-suit-pocket-squareThank Mad Men for bringing the pocket square back to prominence. Nowadays they’ve become so prolific that to not have one almost looks like you’re missing something.

Where to Buy Pocket Squares:

Buy a multi-pack at any of the discount department stores I mentioned above, or (here it comes) on a certain online retailing giant that shall not be named, and get one with multiple colors/patterns.

Just make sure it also includes a plain white one; you can use that one with your navy suit (or any time you where a white shirt), and keep the rest for future shirt/tie/suit combos.

Pro tip:

Mad Men made the razor sharp corners of the perfectly folded pocket square the go-to move for awhile, but the trend has evolved. Fold yours in a way that’s purposely less precise (like in the photo above) to add a bit of personality to your look.

how-to-buy-your-first-suit-tie-barTie Bar

Though not necessary, the tie bar makes a great addition that brings the whole look together and helps set you apart from the crowd a little bit.

Where to Buy Tie Bars:

As mentioned, The Tie Bar has a ton of cool and affordable options to choose from. I also found this cool little online start-up that apparently sells stuff. (Spoiler alert: it’s exactly who you think it is.)

Pro tip:

If you opt for a metallic tie bar, make sure the color matches the metal on your watch and belt buckle.

BONUS:

Socks

how-to-buy-your-first-suit-socks
“And if you’ll just take a look at this tablet, you’ll see — why yes, these ARE new socks. Thank you for noticing.”

Socks are… well, they’re f@¢&ing socks.

You could hardly be blamed for thinking no one’s going to notice or care, and most of the time, you’d be right.

Pull on a pair of navy blue socks that roughly matches the hue of your suit and you’ll be totally fine.

But as you may have gathered by now, in suits, as in life, details matter.

Rocking a pair of socks with a funky pattern or a pop of color is just another way to stand out from the generic-looking crowd.

Where to Buy — Oh, F@$& It

You know where.

how-to-buy-your-first-suit-socks3Pro Tip:

While not 100% necessary, try to keep the colors in the same family as the rest of your get up.

If you’re wearing a burgundy tie with your blue suit, look for socks that utilize those two colors in a cool pattern.

The pattern on the far right in this picture fits the bill, and you can get them as part of a multi-pack with other patterns in the same family.

Your Move:

Use a few of the tips above to sharpen up your new suit and stand out from the crowd.

How to buy your first suit

how-to-buy-your-first-suit-handsomeBONUS:

Step 11: Look Handsome as Hell

If you’ve followed all the steps above, this part will be a given.

You’ve chosen the right suit for you.

You’ve had it tailored to perfection.

You’ve nailed the details by accessorizing.

Now stand up straight, hold your head high, go forth and conquer – actually, that’s a bit much.

Maybe just go forth and confidently be a man of style and substance.

People tend to like that more than conquering.

For more tips about how to step up your style game, sign up for my free email series below and discover nine details that have a huge impact on your overall look—and how to nail them.

Want to Out-Dress the Other Guys?

The (handsome) devil is in the details.

Enter your email address below to discover the 9 Details You Need to Nail.

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Photo Credits:
Waist-measuring photo Douglas LeMoine via Flickr
Custom suit tailor photo Rprakash1782 via Wikimedia
Suit rack photo Robert Sheie via Flickr

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Dave Bowden
A reformed journalist, award-winning blogger and inveterate joker, I founded Irreverent Gent to help guys overcome over-thinking, escape insecurity and take control of their confidence through self-improvement.
  • Silas York

    This is the single most helpful piece on this subject I have found on the Internet-I need a suit within a few weeks and was panicking until I found this comprehensive overview…thank you so much, sir!

    I did have one question: just to clarify, where should I go for the initial sizing measurements for an OTR suit? Would any local alterations shop be OK…and would they charge for it? I live in the Southeast US if that makes a difference…

    Thank you again!

    • Dave Bowden

      Hey Silas! Thanks for the kind words, super glad you liked the guide. For the initial sizing, any tailor or local alteration shop should be able to take your measurements, and I suspect most will do it for free. If you go in and tell them you’re buying an off-the-rack suit, they’ll probably measure you for free with the hope that you’ll bring the suit back to them for the alterations.

      To be safe, you could call ahead and ask if they charge for it – that way if they say they do, you can just call someone else until you find one who will do it for free. As I say, I don’t think it’ll take too long.

      Good luck, and let me know how you make out!

      • Silas York

        Thank you sir! I did have one more question though if you don’t mind: would you say that for the price Banana Republic sells better suits than Mens Wearhouse/Moores? I can get BR’s Slim suit 40% off for USD $340…how would that compare to a $500 suit from MW? My family seems to think I should go to MW…but is BR a better value for money?

        • Dave Bowden

          Hey Silas, sorry for my late reply, I somehow missed this follow-up question. I did a bit of digging and it seems like going with BR when they’re on sale is where you’ll get the best bang for your buck. As an additional tip, go try on the suit in-store to make sure it fits, then go home and buy it online. Before you do, sign up for BR’s email list to get an additional 15% off, which usually stacks on top of whatever other discount they’re currently running.

          To read a bit further on this, here’s a great subreddit I found on r/malefashionadvice (see the comment from “Big Texas_”): https://www.reddit.com/r/malefashionadvice/comments/30qc2v/banana_republic_for_suits/?st=izjtcba1&sh=4c11d821

          Sorry again for the delay! Definitely let me know which one you go with and how you make out.

          • Silas York

            BR didn’t have my size and I was in a time crunch, so I ended up getting two wool suits from MW-one blue and one grey-for the price of one. I feel satisfied and like the way I look…thanks for all your advice!

          • Dave Bowden

            You bet! Glad you’re satisfied with what you got. You’ve piqued my curiosity, too – I may have to go give MW another look.