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How To Dress Better: 3 Rules for Guys Who Want to Upgrade Their Style

Clothes don’t make the man. But they do help. Dressing better boosts your confidence and makes you look and feel better. Here are 3 rules to follow, along with Nate’s personal story of upgrading his wardrobe.

Nate GreenNate and long-time friend (and web developer) Jason Lengstorf.

In March of 2012, after moving to a new city and feeling consistently underdressed in public, I sold or gave away most of the stuff in my closet, put together a list of “wardrobe essentials” assembled from blogs and magazines, and bought new clothes.

No more stupid logo t-shirts. No more too-long, untucked button down shirts. And, much to my girlfriend’s delight, no more helmet hair.

I couldn’t have known it at the time, but dressing better (and getting a new haircut) turned out to be one of the greatest personal investments I’ve ever made, right up there with building a strong, healthy body, and starting my own business.

I felt like a brand new man. Still do, actually.

And I’m not the only guy who looks and feels better after upgrading his style. Take Gabe, a web developer who lives and works in New York:

Gabe StyleThe result of new clothes that fit better and some simple grooming. Photo by Alex Crawford.

According to my friend Dan Trepanier, founder of the men’s style blog TSBMen — the site responsible for Gabe’s makeover — the most exciting part about Gabe’s transformation wasn’t just the way he looked in the “after” photo, but the difference in how he felt.

“His whole demeanor changed,” says Dan. “His posture improved, he was walking taller, speaking more confidently…even his jokes were funnier.”

A haircut and sharp clothes can change a man.

Which is why this article explores three simple rules I followed to upgrade my style. Rules you can use too, if you’re up for it.

But First, Why Care About Style?

Tyler Durden said, “You are not your fucking khakis.”


But Tyler Durden still looked cool. He still had style.

And recent research shows that what you wear affects how you perceive yourself. (So maybe you are your khakis to some extent…)

Tyler DurdenTyler Durden from Fight Club still had style.

So why care about style and the way you dress?

Better first impressions.

“People judge you every day,” says Dan.

“It sucks, but it’s true. The way you look — and the way you dress — is your only true first impression. When you dress well, people act differently toward you. They’re more friendly and approachable. 

In other words, dressing better opens more doors. With potential employers. With potential dates. With front desk clerks, and airline representatives, and waiters, and complete strangers.

Classic clothes last a lifetime.

Think of clothes how you think about food. Some food is high-quality, delicious, and healthy. Other food is complete crap.

Same thing with clothes.

There’s cheap stuff that will fall apart quickly and there are quality clothes that will last a lifetime. (Or at least more than a couple years.)

The more you buy high-quality clothes, the longer they’ll last, and the more character they’ll have.

Case in point: my dad wears a black leather jacket that my grandpa bought over 40 years ago. It’s as classic now as it was back then. And it’ll still be classic 40 years from now.

By buying quality clothes, you’ll also spend less money over the long run as you won’t have to buy a new wardrobe every year or two.

Also note: there’s a difference between “cheap” and “inexpensive.” You can find some great clothes (jackets and shoes, especially) at thrift stores for only a few bucks.

Because it’s OK to care about how you look.

I don’t want to get into the discussion of what a “real man” is and all that, but I do want to point out that how many of the classic “manly” guys care about the way they dress.

They look sharp, period. And it’s at least a small part of the reason they got to be where they are.

Style iconsEastwood. Ali. Craig. Cash.

Ready to Upgrade? 3 Style Rules To Follow

So dressing better makes you look and feel better. But where do you start?

I asked Dan to give me his 3 rules for guys who want to upgrade their style. Here they are, along with some thoughts from me.

Rule 1: Find someone that has cool style.

“Whether he’s an actor, athlete, or blogger – we all have those guys we look at and say, ‘He always looks cool.’ Having a mentor to observe and emulate is an easy way to start feeling more confident about your style.”

I have to give credit where credit’s due. Dan’s blog is the first place I thought “Huh, he looks cool. I want to dress like that.”

So I started paying attention to what kinds of clothes he was wearing. Not the brands of the clothes, mind you. But the actual pieces: a pair of jeans that weren’t baggy. A black leather jacket. Button-down shirts. Shoes that I once would have thought were “too dressy.”

I went through my closet to see what kind of stuff I had that loosely matched. I sold or donated clothes I hadn’t worn or that I knew didn’t look that flattering. And I started strategically buying new pieces.

Dan TrepanierDan Trepanier. (Photos by Alex Crawford.)

Rule 2: Explore slimmer fits.

“Wearing clothes that fit better can make a dramatic difference in the way you look.”

Another way of saying this: most guys wear clothes that are way too big.

For years I wore a size large. As a guy who lifts weights, I just automatically assumed I needed larger shirts. Not true. Most of the time, I was swimming in them. Now I wear a medium or even — and I hate to say this — a small.  I had to get over my ego.

Same thing with pants. Because I told myself that my “legs were too big”, I always went a size or two up. So even though my waist may was 30 inches, I’d get 32″ or 33″ jeans that required me to wear a belt to keep them up.

Luckily, I found a couple brands that fit my thighs while staying true to my actual waist size.   (I’ll share those below.)

One more thing: “slim” is different than “skinny.” No one is saying you should wear skin-tight clothes where you can barely move. The key is to get something that fits your body well and is comfortable.

Rule 3: Plan the perfect wardrobe for your lifestyle.

“Start by investing in quality staple pieces that you will wear most often.”

Personally, I don’t own a suit. When I finally decide to buy one, I’ll probably have it custom-made. I want it to look good and last. But the reason I don’t have a suit is because I don’t really need one.

My lifestyle doesn’t require it since I work from home. (For all you know, I could be wearing pajamas with penguins on them right now…)

Your wardrobe depends on your lifestyle and what you do on a day-to-day basis.

Where do you live? Where do you work? Do you need a rotation of suits or can you get away with more casual wear? Do you want to dress up a little more than the average guy? Or do you only want to wear t-shirts and jeans?

There’s no wrong answer.

But after you make that decision, the key is to buy what Dan calls “staple pieces” — the clothes that will make up the bulk of your wardrobe. The stuff you can mix and match with everything.

For some that may be a navy suit, a charcoal gray suit, and some other “business casual” wear. (To see Dan’s essentials check out this and this.)

For me? Well, here’s what I started with.

THe Casual “Starter” Closet

I always find it helpful when writers actually show me how they take their own advice.

So here are the items I invested in to start building my wardrobe. Remember, I saved up for this stuff. Some of the items (like the leather jacket) will last me for decades.

You do not need to go buy a new wardrobe right away. Instead, just pick the few essential items you’ll wear most often and build from there.

I included brand names and links wherever possible. You’ll notice that I’m loyal to some brands, mostly because I like the way they fit.

(Note: First-time visitors to get 20% off their entire order. Just something to consider.)

Style Homework – 8 Things To Do

Remember: Clothes don’t make the man. But they do help. Dressing better boosts your confidence, improves the way you look, and sets you apart as a guy who “gets it.”

Here are 8 things to do if you want to start today.

  1. Pick a “style icon” or some guy that just looks cool to you. What kind of stuff does he wear?
  2. Go through your closet and take out all the stuff you don’t wear or that you know looks shabby. Ask a trusted friend if you’re not sure what to keep.
  3. Donate the clothes you’re getting rid of.
  4. Of the clothes you’re keeping, try everything on and see if any of it needs to fit better (shirts that need to be taken in on the sides, pants that need to be hemmed). Take that stuff to a local tailor and have them help you.
  5. Make a list of 5-10 items you need to start building your wardrobe around your lifestyle.
  6. Once you have your list, hit up some thrift stores to see if you can find any of it. Don’t worry if the items don’t fit exactly right; as long as they’re close, most stuff can be taken to a tailor.
  7. After the thrift stores, check out sales at the mall, department stores, or online. See if you can find any of your “staple” pieces there.
  8. Depending on your budget, buy a new piece of clothing every pay period until you develop a wardrobe that makes you look and feel awesome.


Nate Green

13 Responses to How To Dress Better: 3 Rules for Guys Who Want to Upgrade Their Style

  1. Carlos Einzberg says:

    I would just like to add to the clothes article on psychology today that even visualizing the movement of your exercises you will train better, or even gain some skills from it. It is still less than physical training. Please be aware that there also might be some unintended influence of the test personal to the volunteers, as well as confirmation bias. (Also our mind is amazing with the placebo effect).

    article: in article):

    (Ans thanks for the hero handbook+workout +scrawny to brawny tips)

  2. Nathan Paul Davis says:

    Oh bloody, too much swag for me to take this article seriously.

    • Nate Green says:

      And by swag, you mean recommendations? :) I’m just sharing the stuff that I personally bought to start building my wardrobe.

      • Guest says:

        The first picture screams to me; “swag;” I would rather try not to take this person as a businessman. Whether it is true or not seems irrelevant if your intending to create good business impressions and fail.

  3. Rob Figulski says:

    Please tell me 5″ shorts are not coming back!

  4. Ian Thompson says:

    Hey Nate, the experience that you describe (“my legs are too big”) sounds awfully familiar. Any advice — recommended brands, etc. — for someone who’s not entirely comfortable ordering pants online? Or who lives in Canada and doesn’t want to pay shipping fees? I think I’m at least one of those two sorts of people.

    • Mark says:

      I’d be interested in this too. Normally, I’m more than willing to pay extra for quality, but buying pants online is an exception.

      Related question. They say not to wear pleated pants because you will look like you have wide hips and legs. What if you already do? Other than don’t keep anything in your pockets.

  5. Tvtimeout says:

    One of the best gifts to give a guy coming out of college is a lesson in shopping for men’s clothes.

    Too bad I’m going through S2B right now, because anything I’d buy may not fit 9 months from now :) However, it also means most of the clothes I currently have will need a makeover, so it’s a great strategy for Spring ’14!

  6. Mike Samuels says:

    Nice blog Nate.

    I always remember a quote from the Hero Handbook when out shopping. (At least I’m pretty sure it was from there and hopefully I’m not misquoting you!) –

    “Buy well and buy once.”

    I now don’t fret spending £70 on a pair of jeans or £30 on a tee shirt if it fits well and I know it will last me. I’d say I spend less now following this rule than I did when I bought stuff that was “okay” and just bought it in the sales.

  7. Eric Bach says:

    Great stuff!

  8. James_Orr says:

    Looking at the examples and Dan’s website, I kept thinking, “Awesome. Instructions on how to be a hipster.” But the shorter shorts are growing on me, and the advise applies regardless of style. What I wonder is how to (once you’ve found someone to emulate) find out where to find those pieces.

  9. Tiger Joe Sallmen says:

    I actually prefer the ‘before’ Gabe in loose casual dress as opposed to the ‘after’ Gabe in tight fitting business attire. I actually prefer loose fitting clothes over snug fits, and it’s a matter of comfort.

    Anyway, you wanna see bad taste in clothes? Check out Anthony Robbins here: