A Simple Formula for Transforming the Way You Dress

Ah, first impressions…

It’s no secret that how you dress and how you carry yourself affect how people perceive you.

Is it fair? No. It’s just human nature.

Deep down, you probably know that improving your personal style would benefit you personally and professionally…But maybe you’re not sure where to start.

It’s easy to get distracted by all the “noise” in the fashion industry. If you’re not careful, you might end up thinking that dressing well is all about fancy designer brands or “what’s hot now.”

Well, I have good news for you: you don’t need any of that stuff to look your best.

You see, by following just a few fundamental principles, you can dramatically increase your style IQ and transform the way you dress.

First…It All Starts With Fit

Remember that saying in real estate about how the three most important things when buying a house are “location, location, location?”

Well, in style it’s “fit, fit, fit.”

No matter what your budget or personal tastes are, you can look about 79.7% better just by wearing clothes that ACTUALLY FIT YOUR BODY (ok, I admit that figure may not be scientifically supportable…but stay with me).

The biggest issue most men have with their clothes is wearing stuff that doesn’t fit.

And more often than not, it’s because their clothes are too baggy. If you’re a slim-ish guy like me, normal off-the-rack shirts don’t really fit around the mid-section.

Even if you’re a bigger guy, you might be tempted to wear things a little looser because you think it hides your problem areas. I’m going to level with you: it’s not doing you any favors.

No matter their shape or size, men look way better in clothes that actually fit their bodies.

I had my own personal “awakening” regarding fit a few years ago. I’ve never been a “style for style’s sake” guy, but one day I had some shirts taken in by a tailor. It cost about $15 extra, but the results were mind-blowing.

After I experienced how well those tailored shirts fit, I basically broke up with the rest of my closet.

People asked me if I had lost weight, they complimented me on how nice I looked…I had a new spring in my step. My clients noticed, my coworkers noticed. Suddenly I had this newfound confidence…and it created what Guy Kawasaki would call “an upward spiral.”

Just to give you a sense of the difference, here’s a side by side comparison of me in an fitted shirt vs. an off-the rack shirt:


Kyle in a fitted shirt vs. an off-the-rack shirt


Such a simple change, right? But what a difference it makes in terms of how you feel and the way people treat you.

Again, so much of your life depends on first impressions—snap judgments people make about you based on how you dress or your posture.

So, it’s no surprise that wearing clothes that fit can make all the difference for getting ahead at work or getting attention from women.

In fact, dating site Ok Cupid and custom suit maker Arden Reed recently did a study to find out how important fit was in selecting a potential mate (er…date, I guess…).

They took two handsome models and created two identical profiles for each of them on Ok Cupid. On one profile, each man wore a boxy, off-the-rack suit…and on the other profile each wore a fitted suit. Then for 3 months they measured the results.

OkCupid/Arden Reed Study: How Fit Effects First Impressions

OkCupid/Arden Reed Study: How Fit Effects First Impressions


Did such a small thing like the cut of their suits make a difference?

You bet it did.

The profiles with the fitted suits got three-and-a-half times more messages from women than the unfitted profiles.

Same guys, same profiles. The only difference was HOW THEIR SUITS FIT!

So, are you convinced that fit is important yet?

Good man.

Now let’s talk about how you can make the philosophy of fit actionable in your life. These are some of the same tips I cover in my step-by-step Style Course:

Step 1: Re-evaluate Your Current Wardrobe With Fit in Mind

Unless you’re homeless or live in a “clothes-optional” camp on the fringes of a wilderness town, you probably have a closet—or at least a place you keep your clothes (but let’s call it a closet for the moment).

And that closet is full of clothes. Clothes that…yes that’s right…probably don’t fit you very well. So, you need to get that sorted out. Plus, now is your opportunity to purge the clothes that you rarely or never wear.

Go through your closet, try everything on and divide everything up into three piles: “keep, alter, and giveaway.”

Step 2: Get Comfortable With Basic Alterations

Remember that “alter” pile we talked about a moment ago? Pick it up off the floor (for heaven’s sake, were you raised in a barn?!). Now, take one of those items to a tailor and get it adjusted to fit you.

You don’t need to go crazy here. For basic alterations like taking in the body of a shirt, you may be safe with your neighborhood dry cleaner. But even if you go with a “pro” tailor, you should still just start with one item—probably a dress shirt. Get a sense of their workmanship before you ruin 20 of your favorite outfits…

Plus, you might be a little wary of the whole “alterations” experience at first. So another reason I’m only asking you to start with one shirt is that once you experience the look and feel of a fitted shirt, I know you’ll be hooked.

Side note: some people think you should only get fancy or high-end clothes tailored. My buddy Brock at The Modest Man makes a compelling argument against that assumption: if fit is so important, shouldn’t you make sure all your clothes fit well? And if you think about it, the less you spend on the original item, the more you can spend on alterations to make it fit absolutely perfectly…

Step 3: Going Forward, Only Buy Clothes That Fit You

If you’ve tackled steps 1 and 2, you’re well on your way to having a wardrobe of clothes that ACTUALLY FIT YOU. Congrats! Now the trick is to keep it up…

Again, the beautiful thing about getting those first few shirts altered and finally having clothes that fit is that you become sensitized to how clothes should fit. Suddenly, you’ll find yourself passing on items in the store that before you might have taken home. “Uh…no thanks. I can fit two of me in those pants!”

As you shop for new clothes, you’ll also notice that certain brands fit you better than others. It’s okay—even encouraged—for you to stick with a few brands if they work better for your unique body type.

You should also fully embrace the new trend of “made-to-measure” clothing. If you haven’t taken advantage of it yet, you’re missing out.

Made-to-measure lies somewhere between off-the-rack and “bespoke” or fully custom. They take pre-existing patterns and adjust them for your unique measurements. So ultimately, you get clothes that fit you almost perfectly…for a fraction of the price of “custom tailored” clothing.

I recently did a video documenting my entire adventure of ordering a made-to-measure shirt through a company called Original Stitch.

But there are a ton of other made-to-measure companies worth checking out, like Trumaker, Indochino, Modern Tailor, and Blank Label, to name a few.

Best of all, most of them have great return policies. So even if you completely mess up your measurements, they’ll help you out and make sure you’re satisfied with the final product.

Wrapping it Up

At the end of the day, you have the power to decide how you want people to perceive you.

And something as simple as how well your shirt fits can dramatically change how desirable or confident you come across…and possibly even make the difference in whether you “get the girl” or nab that next big promotion.

Maybe it’s worth spending a little more time and effort dress your best after all, eh?

Good news is, all it takes is a little bit of basic knowledge and the willingness to improve.

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Kyle Ingham is the founder of TheDistilledMan.com, where he writes about a variety of “gentlemanly” topics. Find him on Twitter and grab a copy of his free ebook, 48 Hour Gentleman: Your One-Weekend Plan to More Confidence, Poise and Manly Know-How.

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