Ten Habits of Highly Stylish People

by   |  in Lifestyle

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.