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How To Effortlessly Look Stylish Every Day

Style doesn’t have to be expensive or take a lot of time

Megan Holstein
Jan 3, 2020 · 9 min read

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:

1. 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.

2. 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.

3. 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.

Here are some guidelines for picking good shoes:

  1. The soles of your shoes should be white, not yellowed (if they are yellowed, it’s easy to make them white again)
  2. The laces, if there are laces, should not be fraying (shoelaces are inexpensive on Amazon)
  3. The color of your shoes (or laces) should not be washed out or faded
  4. If your shoes are leather, the leather should be clean (cleaning leather is also easy)
  5. If your shoes are fabric, there should not be any spots where the fabric is wearing through

Notice that nowhere on this list do I mention brand-name or expensive shoes. You don’t need to be wearing $200 shoes to own shoes that look good. The leather sneakers I wear every day came from a resale shop for $14 (and they are a Target brand, meaning they weren’t more than $50 when they were new), yet people compliment them often.

4. 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.

5. 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.

One of my basic observations about style is people wear what’s in their closet that’s most comfortable. In other words, people tend to select the clothes in their closet that are minimally acceptable for a given occasion, but maximally comfortable. If a woman is going out for the night with her friends, she’s going to select the top that is very comfortable but mildly flattering over the top that is very flattering but mildly comfortable.

This is because humans have a limited amount of willpower, and we tend to avoid using willpower for decisions we make routinely; decisions like, say, what to wear. When we set an intention to dress in a more stylish way, we are facing this natural inclination to wear what is most comfortable.

The solution I’ve found is to work with this natural inclination by only stocking my closet with things I find both highly stylish and highly comfortable.

The good news is that you probably already have everything you need in your closet. Most people own far more clothes than they wear regularly, which means that you can craft a stylish wardrobe from what you already own.

When you have some time, gather up all the clothes you own — yes, all of them, even the things in storage — and ask two questions of them:

  1. Is this comfortable? The answer to this question is not to try it on right now, but to ask yourself how frequently you wear it. Comfortable clothing gets worn often, and uncomfortable clothing doesn’t.

    Another way to answer this question is to ask yourself how often you notice wearing this clothing. Do you ever have to pull at the sleeves, or at the crotch, to relieve discomfort? Or does the clothing seem to disappear onto your body when you’re wearing it?
  2. Is this the kind of thing you want to see yourself wearing? If you saw a photo of yourself wearing this, would you feel good about your appearance? If you had one chance to impress a potential partner, would you feel good wearing this?

Anything which does not get a resounding “fuck yes” is a “no,” and all “no” items should be donated or sold to resale shops at your earliest convenience.

This may inspire a bit of anxiety, or perhaps a bit of guilt. You may find yourself donating a lot of clothes, and feel anxious about how much you’re getting rid of, or perhaps frustrated that you’ve spent so much money on clothing only to now be getting rid of it all.

Unfortunately, all I have to say is: yes, it hurts, but it’s worth it. (In the future, you can avoid this pain by purchasing clothes pre-owned, which allows you to get a hold of nearly-new condition clothes for a fraction of the cost).

A Quick Note About Men’s Style

If I may generalize, most of the people I’ve met who violate these style rules are men. Women seem to be better at intuitively understanding style rules than men, in no small part because we are punished far more harshly for not knowing. In my experience, a man who wears ratty clothes that don’t fit can still succeed in both professional and romantic capacities, while a woman who wears ratty clothes that don’t fit typically fails in both. A man who wears old and dated clothes can still be seen as a competent provider and viable romantic partner, while a woman who wears old and dated clothes is seen in a much less flattering light.

case in point

Style is simply a necessity for success for women in a way it isn’t for men. As a result, women who put effort into appearing stylish generally appear to be ‘typical’ women, whereas men who put effort into appearing stylish come off as stylish, sophisticated men.

If you’re a man, this is good news. It means that investing even a small effort into your style will reap major rewards. If you’re a woman, it means… nothing good, unfortunately. I’m sorry.

At the end of the day, unless you’re running for President as a woman, style doesn’t matter that much. There are many things that are more important in this world than appearance, and most people appreciate that (on some level). But you will get farther with good style than without.

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FootnotesI have no doubt some critical readers will tell me that some folks don’t have the money to go buying new shoes every time their laces fray. I understand this. If that’s you, just do what you can with the closet you have.(1): There are some exceptions, of course; right now, it’s in style for women to wear skinny jeans or leggings along with oversize sweaters and coats. But even in the case of exceptions, there’s a general rule for how big something should be, and what kind of things should be oversize. When intentionally deviating, make sure to follow the example of others.

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