There comes a time in a man’s life when he decides he’d like to dress better and step up his style—and for many guys, this revelation is often followed by another, related one: the sudden realization that you have no idea how to shop for men’s clothes.
One of the most fundamental tenets of menswear is obvious: not all clothes are created equal. If they were, you’d have just as much respect for the guy in the baggy cargo shorts and loose-fitting tank top as you do for the guy in the perfectly tailored three-piece suit.
But the handsome devil is in the details, and a lot of guys quickly come to realize that the reason they have no idea how to shop for men’s clothes is because they don’t know what to look for.
What Guys Need to Know About Buying Clothes
What makes some pieces of menswear superior to others? What sets some clothes apart? And what are the best shopping tips for men who want to improve their look?
After years of pouring over style bibles like GQ and Esquire – combined with far more time than anyone should spend at the mall – I came to discover five fundamental factors guys need to keep in mind when learning how to shop for men’s clothes.
So let’s dig into what matters, and what doesn’t, when looking for clothes that will help you look and feel more confident.
How to Shop for Men’s Clothes
The Five Factors That Matter Most
1. The Most Important Factor (By Far!) is…
When determining whether or not you should invest your hard earned dollars in a piece of clothing, nothing matters as much as fit.
A sweater can look amazing on one guy if it hugs his shoulders and torso perfectly, complements his arms and wraps around his neck just so.
The exact same sweater can look ridiculous on another man if it drapes over his shoulders like a gown, billows out from his hips and hides his arms underneath layers of fabric.
So when trying on a new piece, make sure you’ve got the right size before you make any other judgments.
If you’re a skinnier guy, you probably want to consider sizing down from whatever you’re used to. Growing up as a scrawny kid, my family members were constantly buying me clothes that were one or two sizes too large, on the assumption that I would “grow into it.”
And while I did grow, my basic proportions didn’t change – my shoulders didn’t get much wider (until I started a workout plan and clean up my diet, that is) and my arms didn’t get any longer. So the size large sweaters that I was supposed to “grow into” continued to look ridiculous on me well into my 20s.
It was only after I accepted that in some cases I’m a size Small, not a Medium, that I started to cut a more refined profile.
If you’re on the other end of the size spectrum, the reverse may be true. Just because a medium used to fit you perfectly doesn’t mean it will forever – at some point, you may need to consider moving up to a large in order to make sure your clothes hug your frame without putting it in a death grip.
2. Choosing Colors That Complement You
For years people (and by “people” I mostly mean my mom) would buy me red or orange shirts and sweaters. I really don’t know what motivated these purchases, other than the fact that bright colors probably jump out off the rack and catch the eye of prospective shoppers.
I never had the heart to admit that I would have to relegate these rouge gifts to the bottom of my drawer, or take them back and try to exchange them. You see, while there’s nothing inherently wrong with red and orange as colors, they just don’t go well with my particular skin tone.
I can trace my lineage to one half Irish and one half Italian. In the summers I get pretty tanned, in the winters I’m pretty pasty, and at all times I’m prone to having my nose and face turn red if I catch a cold, blow my nose too much or get too much sun.
As a result, red/orange shirts only serve to bring out the redness in my face, which doesn’t say “I’ve levelled up my life” as much as it says, “I’m on the verge of passing out from heat stroke.”
If you’re not sure which colors will best complement your particular skin tone, I recommend keeping it classic.
You can check out this great color and pattern guide from Men’s Insights to learn how to choose the colors that will complement you best, or take a look at this post for 18 great color combo ideas, and figure out how to work them into your overall look.
3. Crafting a Look That’s Unique to You
How do I know? Because they fall outside of my Personal Style Profile. A Personal Style Profile is a template for your overall look that makes you – and no one else – feel comfortable and confident. It provides a framework for everything you wear that helps you ensure the clothes you’re putting on will make you feel your best.
Let me give you an example. Imagine you’re a young businessman working for a tech startup. You feel at your best in some skinny jeans, a well-fitting shirt, knit ties, Chuck Taylors, and chunky plastic glasses. Your Personal Style Profile is somewhere in between “modern business casual” and “So-Cal skater.”
If that’s the kind of look that makes you feel empowered, then you’re probably not going to drop a thousand bucks on a leather moto jacket, no matter how great it looks on some fashion model (or how tempted you are when you see it in GQ!).
The good news is that creating your own Personal Style Profile is easy. Check out this post to find out how to create a look that makes you feel comfortable and confident.
4. Finding the Right Feel
I have to admit I have a weak spot for those cheap, button-up shirts they sell at H&M for like 15 bucks. They fit so well (which, as noted, is key) and they come in colors that tend to complement my complexion.
See, one of the reasons H&M can sell those shirts so cheap is because they skimp out on the fabric. They use some super lightweight, synthetic material that feels more like plastic than cotton, and it shows when I wear the shirt.
For one, it’s so lightweight that it’s almost see-through, and flashing your nips is never a good look for a young man concerned about his style. For another, it feels more like I’m wearing a cheap Halloween costume than a sharp and put together get-up.
So, while fit and color are important, give some thought to the material your clothes are made of as well. The better a piece feels to the touch, the better it tends to look – and the longer it lasts if you care for it properly.
5. How Much Should You Spend?
It’s not by accident that price comes last on this list.
When it comes to how much your clothes cost, here’s a good rule of thumb to keep in mind: cheap clothes are almost always made cheaply, so if the price is too low, you have reason to be skeptical.
But – and this is key – a high price tag does not guarantee high quality.
There are plenty of brands who price their merchandise at the high end of the menswear spectrum not because their design, fit, material and construction justify it, but because they want you to think they do.
Positioning is a powerful concept in marketing and sales – generally speaking, when we see something priced high, we assume there’s a justification for it, making us more likely to pay that price without thinking much about it.
But there are plenty of great deals to be had on menswear that don’t require you to pay an arm and a leg. When it comes to your local mall, stores like Club Monaco and Massimo Dutti are (in my opinion, at least), frequently over-priced and not worth much consideration.
On the lowest end, stores like Old Navy are cheaper for a reason, though if you choose carefully you can sometimes make great finds there for a fraction of the price. (For instance, their workout gear is quite affordable, and holds up surprisingly well.)
In general, if you keep the rule of thumb in mind, look for sales as much as possible, and be discerning about the price tag of your clothes, you can definitely find pieces that will help you level up your look without bottoming out your bank account.
Oh, and keep in mind that regardless of how much you spend, the devil is in the details. Enter your email address in the form below and I’ll send you an email explaining the nine details you need to nail in order to elevate your look.
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Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a (patient, if long-suffering) Toronto sports fan and the husband of a wonderful (and fortunately much more patient) wife.