Basics on Dressing Yourself (Guy Edition)

Your early twenties are a weird time. Some of your friends are partying every night. Some of them are engaged. Some are even married with kids. Some are in their respective careers, and others are still in school and working at Barnes and Noble. It’s such a weird time and only made stranger because we are supposed to be adults, but no one really explains what that entails. And clothes and wardrobe are even more confusing during this weird limbo of life. That’s why I hope this basic guide on how to dress will help you out. Nothing triggers social anxiety more for me than being overdressed or underdressed. 

If it were up to me, the social norm would be sweatpants, a t-shirt, and an oversized hoodie, but sadly, it’s not. Well, with COVID, it’s more normal to see people in their loungewear clothes, but it won’t be like this forever. 

What you wear to go shopping at Target won’t be the same thing you wear to the bar with your friends or a job interview or a wedding, but what do I wear to those places? Why is picking an outfit so hard? So whether you are reading this to dress a little more your age or if you are looking to fill the holes in your wardrobe, here you go. 

The Essentials

Suits

I stand by it. Every single guy should own a suit. Not just because when you put one on, you look and feel great. Ever put on a tailored suit? Talk about a confidence booster. And please don’t buy a cheap one. If it means you gotta save up for one, then do it. A suit that costs $100 is probably going to start falling apart right away. In the wise words of my mother, “You get what you pay for.” Now, this doesn’t mean you need to spend a thousand dollars on a suit. We’re in our twenties. Most of us ain’t got it like that, but a good number for a quality suit that will last you a good while is about $300-$400, give or take. I know, that’s a PS5. 

Buying a suit can be so confusing and overwhelming. There are some subtle and not so subtle differences in suit jackets that can go over our heads. How many buttons should my jacket have? What kind of pockets? What sort of lapel should I have? The list goes on, but you get the point. 

There are some great articles breaking down suit styles, but the best one you can use is just going to Indochino. You get to sit down and figure out what you like most in your suit without it ever getting too complicated. Honestly, it’s suit shopping made easy. 

As for the actual suit, if this is your first one, make sure it’s navy blue. You can wear navy to almost any event that you’ll need to wear a suit. It’s perfect for weddings, interviews, anniversaries, and so on. It’s the most bang for your buck. 

Oxford Shirts 

This should be a staple in your closet. This might be the most versatile piece of men’s fashion. You can wear this with your navy suit for work or dress it down with some jeans and sneakers for a more casual look. You can wear an Oxford with almost anything, and it’s a step up from the graphic-t that we all love. 

Honestly, my favorite place to get my Oxfords is at American Eagle. They have the basic colors and some nice patterns to pick from if you want something other than a solid color. 

Jeans

While you are checking out Oxfords at AE, you should check out their jeans. Their jeans are the best. 

The worst thing about jeans is how uncomfortable they can be. I mean, no guy wants to chafe every time they wear jeans. And if you’re like me and your body isn’t a twig, then American Eagle is where it’s at. They have different cuts of jeans for different kinds of body types. It’s the best. My favorite is the athletic fit, but you have to try them out to find what is most comfortable for you. 

In terms of the actual jeans, the best color to get is dark blue. It goes with everything. And if you want a second pair, black is always a good bet, and make sure to grab a pair of khakis too. Just take your time, and try on a few different sizes to see what fits the best. And if you’re not sure, then don’t be afraid to ask someone who works there. They will be glad to help you out. They are jean experts. Trust me. I used to work in the backroom of an American Eagle. 

Crewnecks and Polos

I get it. You don’t want to wear a button-up all the time. I can’t blame you, but that doesn’t mean you can’t still look good. The hardest thing about crewnecks and polos is finding ones that fit you well. Some people have no problem with this. Lucky them. Some of us can’t find clothing that fits perfectly on us off the rack. It sucks. My shoulders are an XL, but the rest of my torso is large, so most crewnecks and polos are too big or too small. The struggle is real. I feel like Goldilocks looking for the perfect porridge. 

In all seriousness, my favorite crewnecks and polos are from Banana Republic. They can be a little pricey at times (though you can find great finds on their sales rack), but there is no beating finding shirts that fit me properly. 

Don’t be scared to mix it up when picking out your shirts. You should definitely have black, white, and grey crewnecks, but when it comes to picking a polo, have fun with it. Pick some fun colors or patterns that can act more than just a basic piece. 

Outerwear

I’m the biggest fan of oversized hoodies that you will probably ever find. On rainy Saturdays, you will find me in an oversized hoodie watching movies or reading all day. You can bet on it. 

But you can’t wear hoodies all of the time, and there are so many types of outerwear. What kind should you even consider? I think to start, the best three pieces of outerwear every guy should own are a crewneck sweater, a cardigan, and a bomber jacket. 

The crewneck sweater is perfect when it’s not cold enough for a jacket but still a little nippy out. Grey is a great color choice. It goes with most of the other things in your wardrobe like the blue jeans and oxford you bought. 

A cardigan is just so classy. I mean, there’s a reason Mr. Rogers wore them. And let’s be honest, we should all strive to be a little more like Mr. Rogers. 

A bomber jacket is great for when you want to look good and feel good. They go great with a t-shirt and jeans or paired with trousers and a collared shirt. You can wear them casually when you hang out with friends or dress them up a little for a nice birthday dinner with your friends where you might not need something so formal. Just match the style and color with your overall outfit, and you’ll feel like a million bucks. 

Accessories

I’m not a big fan of jewelry on my hands and wrist. Bracelets and rings get so annoying. But that’s not everything when it comes to accessories, especially for guys. I wear glasses, my ears are pierced, and I have a septum piercing. Those are all accessories that I can work with to add little touches to my outfits. I tend to go all black on all of them just because I like how it looks. 

Glasses

f you wear glasses, then maybe the next time you need a new pair go to LensCrafters and ask the people who work there what frame looks best on you. It took me a while to find a pair that I liked. I look back on my old frames and cringe at how weird and small they look on my big head. And no, don’t buy your frames from those places. You shouldn’t be spending $400 on frames just because they are name brand. There are some great websites out there with affordable frames. You just need to know your prescription. I bought my newest pair at Glasses USA. 

Watches

A nice watch can really up your outfit. You don’t need anything big or gaudy. I hate G-Shocks. You don’t want something that is going to distract from your outfit but complement it. My favorite watches are from Fossil because they are nice, affordable, and customizable. 

Shoes

Shoes can make or break your fit. You wouldn’t wear your beat up skating shoes with a suit, right? 

White sneakers are perfect for casual outfits. 

Laced-up boots are great for more semi-formal outfits. You can wear these to work and on the weekend. Their greatest trait is being stylish and versatile. 

Brown dress shoes are a must. We all need a pair of nice formal shoes for job interviews, internships, or weddings. If you take good care of them, then they will be the only pair you will need. 

To sum it up

Being an adult can be overwhelming at times, especially with how confusing your early twenties can be. I’m almost 24, and I have a full-time job. I pay rent and bills. I cook for myself. (Most days.) My taxes say I’m independent, but there are days that I don’t feel like an adult. Imposter Syndrome at its best. I know this is cliche, but “faking it til you make it” really is the motto of getting through this weird transitional time in life. And there is no better way to fake it than looking the part, so hopefully, this guide on the basics of dressing yourself helps out. 

Sometimes, we can lack confidence in the clothes we wear because we don’t look or feel the way we want. It can be hard to take care of yourself. The first step is healthy sleep habits. You can read more on that here.