One of the unfortunate realities of the world we live in is that even though we know we shouldn’t, we judge other people based on their appearance.
Here and there you find a rare soul who has learned to look past appearance, but for the most part, people are going to judge you based on what you look like whether or not they should.
Most of the time, this doesn’t matter. But sometimes it does — like when you’re interviewing for your dream job, when you’re going on first dates, and when you’re stopped by police officers for speeding. The impression you make in situations like these can have a real, measurable outcome in the quality of your life.
For a long time, I knew nothing about style. I wore clothes that didn’t fit, that were too small or too large, that were ratty, mismatched, and generally just not something in which I should leave the house.
Obviously, the clothes I wore on the outside didn’t determine who I was on the inside — but they sure as heck determined what people thought. Once I figured out how to dress myself in clothes that fit and matched well, my life changed in surprising ways.
I started being offered jobs at trendy companies downtown, professors wanted me in their private seminars, and people wanted to take me on dates, because I now looked the part.
The good news is, style can also be fun. You can still use clothes to express your unique inner self and make a good impression on those who matter. You don’t have to keep up with fashion or know the latest trends (I certainly don’t). All it takes is knowing a few timeless guidelines:
- Only wear clothing you find comfortable.
No one looks good if their clothing is uncomfortable. Why? Because people walk differently in uncomfortable clothing. When you’re wearing uncomfortable clothing, you’re constantly adjusting it. You’re walking funny to compensate for how uncomfortable it is.
Most importantly, when you wear uncomfortable clothing, you’re constantly thinking about when you get to go home and take off your uncomfortable clothing and put on some damn pajamas. That kind of distraction will make any work or social event unpleasant and will make you more likely to cut and run. Do yourself a favor, and only wear clothes that are comfortable enough that you forget you’re wearing them.
- Wear clothes that fit
Of all the style sins out there, this one is probably the worst. It doesn’t matter how cute a shirt is, what a great color it is, or how trendy it is if it doesn’t fit, because if it doesn’t fit, it won’t look good(1).
How can you tell if something fits?
Typically, to ensure something fits, you buy the smallest size you can fit on your body that still allows you a full range of motion. For pants, you should buy the smallest size that still allows you to squat, twist, kick out your legs, or lounge comfortably. For shirts and coats, you should buy the smallest size that still allows you to raise your arms, clasp your hands in front of and behind your back, and otherwise provides you full flexibility. Your clothing should make you look good and flatter your form without being painted on your body or causing you pain at the joints and seams.
Clothing that fits tends not to be too wide at your arms and waist. Clothing that fits is an inch or two wider than your body at the openings for the arm and waist, but isn’t billowing.
Furthermore, clothing should be able to stay on your body without an unnecessary amount of belts, straps, buttons, or zips being done (or undone). If you need to wear a waist belt with that shirt in order to make it look good, the shirt is too big. (The obvious exception here is belts for men’s pants).
If clothing has belts/straps/buttons/zips/fasteners of any kind, you should be able to fasten them all up without issue (unless they are intentionally designed not to be fastened). You shouldn’t own jeans for which you can’t button the top button or coats for which you can’t button the bottom one.
Just because you think it fits, doesn’t mean it does
Most of the people I’ve met who wear clothes that don’t fit can’t tell they don’t fit. They’ve always worn clothing that’s too big their whole life, so they feel like clothing that fits is constricting and uncomfortable.
To check and make sure you’re not one of these people, just head to the store and apply the above fit rules. If you find that one size smaller still allows you a full range of motion, chances are the clothes you’ve been wearing are too big.
Pick the right shoes
The one thing that can bring an outfit down most quickly is shoes. If someone is wearing a three-piece suit and muddy sneakers, they will look bad — but if they are wearing track pants, a gray tee, and brand-new Air Jordans, they will look good.
Use this principle to your advantage, and pick good shoes. No, I don’t mean pick expensive shoes — it’s easy to find sharp shoes for cheap prices if you know where to look. I mean pick good shoes.
Avoid clothes that are worn out.
Are your sleeves fraying at the hems? Are your novelty tee designs cracking? Are your jeans ratty at the cuffs? If you have any clothes like that, it might be time to make them pajamas instead.
You may not notice these things because they’re your clothes, but other people will. It’s not as if people will spot these flaws and judge you harshly, but it will contribute to an air of being unkempt and ruffled — and if you’re reading an article about how to appear stylish, I doubt that’s what you want.
Avoid dated styles
I’m not saying you have to buy new clothes every year to keep up with every stupid fashion trend, but do try to stay abreast of the major style changes going on in our culture. For instance:
Slim-fit jeans have been in style for the last seven years, and probably will be for the next seven as well. If you have any boot cut or flare jeans in your closet, it’s time to let them go.
Square-toed shoes are a trend, and they’re a trend that has been out of style since the late nineties. Round-toed shoes, on the other hand, are a classic that never go out of style.
Cargo shorts — and indeed, any shorts that extend below the knee — haven’t been in since the nineties. If you’re a man with long shorts in his closet, it’s time to switch them out for something that ends at the knee instead.
If you’re wondering what is and isn’t dated, just take a look at what people age 25–30 are wearing. People in that age group are typically old enough that they aren’t taken in by stupid fashion trends, but young enough that there aren’t clothes from the nineties hiding in their closet.