The following is a guest article from Nate of Iron & Tweed. This is a good one! Pay attention.



Have you ever noticed the way some guys are able to look better in jeans and a T-shirt than others do in a suit?

Everything about their look seems comfortable, confident, nonchalant yet deliberate at the same time.

What is it about these individuals that sets them apart?

Anyone remotely interested in style strives for this effortlessly cool way of dressing. While it may come naturally to a rare few, for the rest of us it takes some work to pull it all together.

Wouldn’t it be wonderful if we could just copy what we see and be guaranteed a perfectly polished style? In reality, there’s no set-in-stone formula for being stylish, such as “well dressed women carry this brand of handbag” or “stylish men always wear suits”.

It’s more complex than that.

Fortunately, there are some common habits amongst the naturally style-inclined that you can emulate. Here’s a list, along with my tips on implementing these habits in your daily life and becoming the confident, stylish man you want to be.

1. They don’t have a closet full of “comfy” clothes

How do you dress impeccably day in and day out? Simple: don’t give yourself an option to do otherwise.

If your wardrobe is full of hoodies, graphic tees, and running shoes, you can bet that’s what you’ll gravitate toward.

If you limit these items to just one set for yard work or painting, your choice is between looking great and looking even better. It’s a win-win situation!

You don’t always have to be formally dressed, but it’s best not to make a habit of looking sloppy, even around the house.

Tip #1: Donate your comfy clothes and invest in classic staple items.

2. They buy pieces that get better with age

Besides saving cash and being less wasteful, buying pieces built to last will give you an incredible aura of style. Well-worn items send the message that you know exactly where to spend your dollars.

Natural materials are the name of the game. Leather, denim, canvas, and wool all tend to develop a beautiful patina with normal use. Stylish people avoid items made of synthetic materials and faux design details.

Tip #2: Take your time when deciding on purchases. Read reviews and look for designs that haven’t changed much over the decades.

3. They dress for the weather

Stylish people know that soggy oxfords aren’t impressing anyone, so they embrace the practical accessories. Why do you think brightly colored wellingtons and rain coats are fashionable?

Stylish people made it so by proudly donning the necessities without shame.

Never be afraid to grab a rain coat or umbrella if the weather calls for it.

Tip #3: Get yourself a good pair of waterproof boots, a heavy parka, or a raincoat/umbrella to be prepared for your local climate.

4. They always “get dressed”

Stylish people make it a point to get dressed everyday, even on the weekends. They don’t lounge around until noon and then decide to stay in because they aren’t ready.

When you always look presentable, you’ll never have to miss an opportunity to grab an impromptu drink with friends, talk to that cute girl in the supermarket, or chat with a prospective business partner.

Tip #4: Being well dressed is like any other habit. Do it first thing in the morning, consistently, before you have a chance to change your mind.

5. They’re never “up to the minute”

Stylish people always find the middle ground. They’re up-to-date without being too trendy. They’re classically dressed without appearing stuffy.

Fashion changes so fast, especially with the internet, that trying to keep up will leave you broke and exhausted. The goal should be to dress in a way that doesn’t make you embarrassed of old Facebook photos.

Tip #5: Stick to classic designs for things like suits, shoes, and outerwear, then have a little fun experimenting with trendy accessories.

6. They don’t wear athletic clothing unless they’re working out

Gym clothes belong in the gym, running shoes on the track, and your North Face jacket should be reserved for the trail.

Tip #6: Try only owning enough gym clothes to get you through a week’s worth of workouts. Anything more is a waste of space.

7. They dress like themselves, not like a (any) certain celebrity

Stylish people take inspiration, but never blindly follow.

Developing personal style is the most difficult part of being well dressed. Throwing money around to look like so-and-so is easy, but you’ll never really feel like yourself.

Tip #7: Experiment with thrift store and discount items until you find a style that works for you: both functionally and aesthetically.

8. They aren’t label fanatics

Stylish people know that specific labels can give you general ideas about fit and quality, but won’t guarantee sartorial success. They also don’t buy pieces that are shamelessly branded.

No one should be able to tell what brands or designers you’re wearing at first glance.

A truly stylish wardrobe is one of diversity. High-end staples, vintage statement pieces, and discount brand basics.

Tip #8: Avoid anything with an obvious logo. It’s perfectly fine to like a brand because of fit and quality, but not just to impress your friends with a label.

9. They don’t know their size

In some shirting brands, I wear a small, and others, a large.

I can’t recall a single time I’ve bought a clothing item from a brick and mortar store without trying it on first. There’s too much variation between manufacturers and fits.

Tip #9: Know your measurements when ordering online, and try things on in stores whenever possible for the right fit.

10. They’re comfortable in their clothes

This statement is two-fold.

Stylish people take great care to make sure their clothes fit properly and are physically comfortable.

But they’re also comfortable with themselves. They’re confident.

No matter how expensive or “in” a jacket may be, if the wearer is self conscious about a loud pattern or bold color, the look will fall to pieces. Being unsure of yourself will ruin the most important aspect of being stylish: confidence.

Stylish people buy clothing that fits their personality and lifestyle. No drop crotch pants just because they’re on the runway right now.

Tip #10: This is the big one. Buy clothes that you’re excited to wear and feel great in. Confidence will follow.

With consistent application, following even a few of these steps will help you build a wardrobe and instill habits that will naturally result in the confidence exuded by these highly stylish individuals.

Now, tell me…

How many of these habits do you recognize? Do you put these into practice? Would love to hear your thoughts in the comments below.

Learn a few shortcuts to dressing well

Enter your first name and email, and I'll send you a free eGuide with quick and easy tips you can use today.

20 Responses

  1. Wes on

    You forgot one thing. They are without a doubt or exception, always healthy, thin people. Or at least thin ish. Fat is never stylish.

    • Nick P. on

      Yes and no, I have seen some large men and women (though less for women) who are extremely stylish and have impeccable attention to detail and fit. I agree that being fat is not stylish, in and of itself, but that does not negate that people of less than healthy stature are not stylish.

      • Tod C on

        Good article Nate – I try and follow most of these already (even if I came about doing it by making a lot of mistakes).

        Certainly fitness forgives a lot of ills you need to work around if you aren’t thin. I am carrying about 20 pounds more than my optimal weight and I have to really watch the fit of shirts, drape of trousers and the cut of my jackets as a result. So I degree agree with your point but people tend to expand a bit as they age so you will need to prepare for that.

        As far as women go I find the opposite – as they have more wardrobe options in general a lot of bigger women (healthy still but not skinny) look great if they play to their strengths. Part of that might be the definition of thin – I certainly find many women unattractively skinny.

        • Nate on

          Thanks Tod! Making mistakes is how we all learn. It’s great that you know what works best for you. It’s a key skill of stylish people.

          Don’t give up hope though, it’s never too late to fight the expansion.

      • Matthew on

        100% without a doubt, size does not affect how stylish you are. Confident is the #1 indicator of a “stylish person”. Without confidence, they’re just clothes on a form.

        I’ve been all sizes and find it key to make sure clothes fit well at any size. Too big or too small (regardless of size, ie tight sleeves around muscles) will always look messy.

        • Nate on

          Great point Matthew. It’s all about learning how to dress in a way that makes you feel comfortable.

          I’ve also been a few different sizes and have always had a difficult time finding things that fit off-the-rack.

          Whether you’re slim, chubby, or muscular each body type comes with its own challenges.

        • Dan J. on

          I disagree with your first statement. Size does matter. It’s not the be-all and end-all. It doesn’t mean that if you’re oveweight you might as well not even try. But Barron starts this article talking about guys who look better in jeans and a t-shirt than most guys do in suits. Those guys are seldom if ever overweight. If you’re Brad Pitt, you look great in anything. If, like me, you’re Not Brad Pitt, it takes a lot more effort and attention to detail. Heavy guys can look good but they usually have to step up the formality a notch or two to compensate. Very few overweight guys look good in jeans and a tshirt, even perfectly fitted, high quality jeans and tshirt.

    • Nate on

      I’m definitely an advocate of staying fit, it makes dressing well so much easier. I have seen some larger men who were impeccably dressed, it just takes more effort.

      When bigger guys do look good, it’s usually because they’re dressing for their bodies and not trying to wear the same style as their thinner friends.

  2. Bo on

    Definitely agree with No.’s 1, 4 and 6 especially — I’ve (perhaps somewhat unconsciously) phased out all of my “comfy” clothes for daily wear (even on the weekends) simply because I don’t think it looks polished and I just don’t like to wear that kind of gear anymore. I’ve also pared down my workout clothes to no more than a week’s worth of workouts (kind of goes with No.1, too) and I definitely make it a point to “always get dressed” — it’s kind of crazy how those simple things really will improve your style ten-fold!

    • Nate on

      You’re spot on Bo! You could spend all the time and money in the world putting together the perfect wardrobe, but if you’re stuck in the habit of wearing workout gear, it won’t do you much good.

      We buy nice clothes to look and feel good. I say, wear them as often as possible.

  3. Glen on

    #9 reminds of a buddy of mine. I know my size and I also try everything on to make sure the item isn’t too long as I’m short. My friends give me shit for taking so long. So my buddy buys a shirt with his correct neck/arm size and tries on that night at home, French cuffs. Doesn’t own cuff links=expensive rag. Same buddy, similar story, different shirt. This time, the shirt has a placket cover; added to the rag pile. When possible, try before you buy.

  4. Adam Aguinaga on

    This is a great post Nate! I really relate to number 6 because it is a pet peeve of mine to see people wearing gym clothes everywhere. I do work out a good amount and looking to get a job it that, but I hate wearing them more then I have to. I’ve always avoided overt labels, I guess it’s for the mystery. But you have hit it right on the head and it gives us some good pointers. I’ve been aspiring to get to this level, just haven’t reached it yet.

    • Nate on

      I know what you mean, Adam. When I’m in the gym and look out the window, there’s a steady stream of people in gym clothes walking my way. But about half of them go next door for brunch. Go figure.

  5. Sirilly on

    I can honestly say I’ve grown into all these habits naturally, not to brag though. I’ve always been ocd about everything and it just so happens me and my meticulous ways have paid off. Thanks for the reassurance though, because I’m kind of in a style rut right now (all neutrals boring!) but I really can’t afford to buy anymore clothes. Otherwise I’d be living beyond my means. This makes me feel a lot better though. Thanks Nate!

  6. Michael Blind on

    Great Article! Noticed I’ve been subconsciously doing most of them but Number 2 was a first. It sounds like solid advice and I’m going to try and take it into consideration when buying clothes. Awesome Job and keep it coming!

  7. Gazman on

    #11 – They don’t care what others think; they dress for themselves.
    #12 – They don’t mind shopping and they buy their own clothes, No GF or wife in tow.