How to Dress for (Social, Professional & Romantic) Success

Pop quiz: which of the two guys here would you rather talk to?

OK, same picture, new question: which one do you think someone else would rather talk to… or hire… or date… or interact with in any way, shape, or form?

Chances are it’s not the guy with the dishevelled hair, who looks like a total mess (despite the fact that his chambray shirt game is on point).

These two stock pictures of the same model perfectly demonstrate the way that investing some thought and effort into your appearance can make people see you as a much more appealing social, professional or romantic prospect.

As I’ve written many times before, when you look good, you feel good. But not only do you feel good, you make other people feel good about you—which makes communicating with them a helluva lot easier.

So to wrap up our series on how to look like someone worth talking to, let’s explore a few things you can do to sharpen up your look and put your best self forward.

Dress for Success Men:

A Head-to-Toe Checklist for Looking Your Best

1. Your Hair: On point, or unkempt?

Let’s start with an obvious one. Your hair is one of the first things people will notice about you.

Make sure you’ve got the right cut to fit your head shape, the right product to maintain your style, and that you put at least some effort into maintaining it before you leave the house.

Not sure where to start?

Check out this guide from Real Men Real Style, which lays out everything you need to know about choosing the right style for your head shape, and (crucially) explaining what you want to your barber.

2. Your Face: Smooth, Stubbled, Scruffy, or Scraggly?

Moving down from the hair on top of your head, let’s talk about the hair on your face.

Whether you opt to go clean shaven, keep some stubble, or grow out a beard, make sure your facial hair looks well maintained.

This is an easy step to skip – let’s face it, shaving can be a boring chore, and sometimes a real pain in the ass – which is exactly why you should pay attention to it.

The good news is that studies have shown that women prefer guys with stubble to guys who are clean shaven.

But if you’re going to go all Grizzly Adams, you still need to make sure that you keep your beard well groomed. (There are exactly zero studies suggesting that women like a guy with neck hair.)

Pick up a good beard trimmer (I swear by the Wahl Lithium Ion) and make sure to clean up your neck and jawline at least once or twice a week.

A good beard can say, “I’m a masculine man capable of taking care of myself and those around me.”

A bad or unkempt beard says, “Neither the old refrigerator box I live in, nor the alley in which it’s located, has a good place to shave.”

3. Your Shades: Helping, or Hindering?

The right pair of sunglasses can instantly make a man look cool.

The wrong pair, however, can make you look like you have no idea how to dress like a grown up.

As a general rule, remember that sports sunglasses are ONLY for sports.

If your shades are labelled Oakley, Adidas, Nike or any other athletic brand, do not wear them in casual, social or professional settings.

To help you figure out which frames make your face look best, check out this post outlining seven of the most classic men’s sunglass styles.

Any of the options listed there will help you shield your eyes in style.

4. Your Collar: Standing Strong, or (ahem) Flapping Flaccidly?

Moving down from your face to your neck, let’s discuss a mistake I see far too many guys make with their shirt collars.

While men, of course, consist of multitudes, your shirt collar can only convey one of two options: either you’re stiff, or your flaccid.

(I don’t think I have to tell you which one is preferable…)

To keep your collars from flapping listlessly, try using magnetic collar stays like Wurkin Stiffs.

Slide the metallic stays into the slots on the back of your shirt collar, then use the small magnetics to keep your collar standing up straight.

Below is a quick 1-minute video demonstrating how they work and here’s the link to where you can find them on Amazon if you’re interested.

5. Your Button Stance: Too Much, or Just Right?

Still got those little magnets from the collar stays?

Good, because you can also use them to make sure your collar is always unbuttoned the perfect amount.

On the chest hair spectrum, I personally fall closer to the Robin Williams end than the Justin Bieber end.

And while, generally speaking, I’d rather fall on the Robin Williams end of any spectrum than the Justin Bieber end, when it comes to chest hair, it can make leaving my shirt collar unbuttoned a bit awkward.

Often, undoing only the top button can look a little stuffy, especially in warmer months.

But many shirts have a low button stance, meaning that if I undo the second button, my chest hair pours through the collar like an unwanted waterfall of body hair.

Fortunately, the menswear blog Dappered has come up with a perfect solution: you can use the small magnets that come with Wurkin Stiffs to basically create your own button in between the first and second buttons on your shirt.

Check out their post to get the full details on how to always show the right amount of skin (and the right amount of chest hair, which of course is as close to zero as possible).

6. Your Belt: Don’t Waste Your Waist!

When your belt goes well with your shoes and watch band (more on those below), it can help tie your entire look together and contribute to an overall sense that you’re a guy who knows what he’s doing.

But when you cinch some monster-sized leather strap with a big gaudy buckle around your waist, it doesn’t make you look like the World Heavyweight Champion; it makes you look like a kid wearing a cowboy costume.

As a general rule, you want your belt, watch band (if it’s leather) and shoes to match, or at least be in the same family.

That means DO NOT wear brown shoes with a black belt, or vice versa.

Also give some thought to the width of your belt.

If you’re wearing business casual or anything fancier, you want to keep your belt pretty narrow, in the 1 to 1.5 inch range. If you’re rocking a more casual look, you can go with a belt that’s up to 2 inches wide.

Again, I cannot stress this enough: only wear a belt wider than that if it was handed to you by the ref after your come-from-nowhere victory over Connor McGregor.

Here’s your perfunctory Amazon link, where you can find literally thousands of good belts at decent prices.

And here’s how to measure your belt size to make sure you get the perfect fit.

7. Your Watch: Got the Right Wrist Game?

With watches, you want to follow the same rule as sunglasses:

Leave the athletic, sporty designs for the actual sports.

Baseball helmets have visors that block the sun, but you wouldn’t wear one around to run errands and get groceries, right?

(Please tell me you wouldn’t.)

Likewise, leave the sporty watches for the field. For day-to-day wear, opt for either a metallic or leather band.

And again, if you go with leather, make sure it matches (or closely mimics) the leather of your belt and shoes.

Also, note that if you go with a metallic watch, you ideally want it to match any other metal pieces you’re wearing, namely your sunglasses and belt buckle.

And just like with belts, you don’t want to go too big.

8. Your Socks: Are Your Ankles Out of Place?

Yes, we’re actually talking socks.

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

But the whole idea of this list is to nail the details, remember?

Pull on a pair of socks that roughly matches the hue of your pants and you’ll be totally fine.
But as you may have gathered by now, you’re not just going for fine. You’re going for stylish.

Rocking a pair of socks with a funky pattern or a pop of color can help you stand out from the generic-looking crowd.

I have literally had people (and by people I mean women, who tend to notice these things far more often than guys) tell me “Hey, I love your socks!” That’s a good feeling.

While not 100% necessary, try to keep the colors in the same family as the rest of your get up. Pick up a couple multi-packs with various color patterns and you should be all set.

Bonus: Skip the Socks Entirely

If the weather’s warm enough, sometimes the most stylish thing to do is rock the sockless look, but be warned: if it’s especially hot (or you’re especially sweaty), you’ll risk exposing those around you to the smell of a foot funk.

If you’re going to try it, check out this post about how to go sockless while avoiding shoe stank.

9. Shoes: Got the Right Kicks for Your Kit?

And finally we come to your shoes, the secret weapon to stepping up your style. (Pun very much intended.)

When deciding which shoes to wear with an outfit, first ask yourself what overall look you’re going for.

Is it casual and laid back? Rugged and masculine? Sleek and refined?

Whatever it is, make sure your shoes fit into that template. I see far too many guys wearing a sleek suit with a clunky and casual pair of shoes, which ruins the entire get up.

A great little hack to step up your shoe game is to apply the 10% rule – that’s when you dress 10% better than you have to in any situation – specifically to your shoes.

If all your friends wear boat shoes all summer long, try showing up in a good pair of brogues or some stylish suede oxfords.

In the casual office where I used to work, 90% of the guys wore casual chelsea boots most of the year.

I opted for the slightly dressier Karnes cap toe from Johnston & Murphy, and received frequent compliments for my marginally more stylish choice.

Remember, your shoes should complement and complete the overall look you’re going for, not detract from it.

If you’re able to step it up a little and throw on a pair that you think will also help you stand out from the crowd, all the better.