How To Dress in Your 20s: Male Edition

hen it comes to dressing as a man, the truth is that the bar can be pretty low. As a man in my twenties myself, I have noticed time and time again how guys my age refuse to wear anything but shorts, t-shirts, and hoodies. Sure, shorts, t-shirts, and hoodies are comfortable, but putting a little more thought into your outfit can yield some real benefits. Dressing well can let you stand out in the crowd, improve the way you’re viewed by others, and even increase your confidence in day-to-day life.

There are plenty of ways to improve your style with the way you dress, but if your closet looks the way it does for most guys, it may be time for a trip to the thrift store. In this post, we’ll help you improve your wardrobe and teach you the following:

• How to Find Your Style - how you can discover what you look best in
• Where to Find Your Style - how to find affordable threads for all styles

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How To Find Your Style

If you’re looking to improve your style, then first you need to find your style. What kind of outfits speak to you? There are plenty of looks to choose from, or mix and match to create something new. But as a man, the first step for finding your style is deciding what you will wear for specific occasions.

Men’s clothing styles can typically be divided up into 5 categories:

• Casual - Fashionable but comfortable and not too over the top.
• Smart Casual - A mature outfit to match slightly more important occasions.
• Business Casual - A semi-professional but not formal look for work.
• Business Professional - A professional and intelligent look for formal occasions.
• Cocktail Attire - A snazzy and elegant outfit for functions and parties.

These are styles that you can follow by definition, or customize based on your own personality. If you’re looking to develop a well-rounded style, you should consider putting together a couple of outfits for each of these styles. At the very least, you should have a casual style for everyday outings and a more professional style for special occasions and formal meetings. Here are some ways to customize each of these five styles.

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Casual

Casual, while the least fancy of the styles, can be the most important. When we say casual in terms of style, we’re not talking about sweatpants and slides, we’re talking about a leisurely and comfortable outfit that still has some thought put into it. This is what you'll wear every day when you’re out and about, like at school or out on the town.

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Here are some of the kinds of clothing items you’ll want to consider for a casual style.

• A good pair of jeans
• Solid color t-shirts
• A thin jacket 
• Accessories like scarves, necklaces, or bracelets.

Here are some of the kinds of clothing items you might want to avoid when you’re trying to develop your casual style.

• Sweat pants
• Workout clothes
• Sliders or flip-flops
• Old/worn-out sneakers

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Smart Casual

Smart casual is just a small step above casual. You’ll want to go smart casual when you’re out having a nice dinner, at a wedding, or at a particularly important birthday party. This can be one of the most versatile looks you’ll have, so I’d recommend putting together a variety of smart casual looks. We’re not thinking formal or a suit and tie, but instead something in-between casual and formal.

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When putting together your smart casual look, you should consider the following clothing items.

• Long-sleeved shirts
• Button-ups
• Blazers
• Chino pants
• Leather shoes or boots

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Business Casual

Business casual is one step above smart casual but still less fancy than a suit-and-tie look. This is what you’ll want to go for if you’re working in an office environment or a traditional workplace. This is also the way that your professor might ask you to dress for an important presentation. Here’s a tip — for business casual, just take the business professional outfit you would ordinarily use (like a suit and tie) and just take out the tie and/or the blazer.

When you’re putting together your business casual look, you’ll want to look for these kinds of items:

• Button-ups with collars
• Slacks
• Dress shoes
• Accessories like a watch or a hat.

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Business Professional

Business Professional is your go-to look for important professional occasions. This look is pretty simple because a suit and tie with some dress shoes will work just fine 100% of the time. Something to consider is that for the business professional look, you’ll want to keep the suit a solid, dark color as opposed to a bright, primary color. In professional settings, it’s best to keep things tame with a black, grey, brown, or navy blue suit. Save your more flamboyant blazers and slacks for your cocktail attire. This is also what you should wear to job interviews.

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Cocktail Attire

Your cocktail attire will be for your more high-end functions and parties. Think fun formal instead of boring formal. The most common cocktail attire for men is a three-piece suit with a blazer, tie, dress shoes, slacks, and a vest. Your aim here isn’t to look professional so much as it is to look elegant. With cocktail attire, you can go crazy with the colors, combinations, and accessories to your heart’s desire. 

Here are some common additions to a three-piece suit for cocktail attire

• Hats like a fedora or a flat-cap
• Watches
• Bow-ties instead of normal ties
• Loafers
• Pocket squares

A great place to start in terms of improving your style as a man is to put together some looks for your casual, smart casual, business casual, business professional, and cocktail attire styles. The best way to find your style is to just try on what you can and see what you feel good in!

Once you become more familiar with what you feel good in, then you may even want to branch out into more unique styles like dark academia, Y2K, goth, or techwear.

But where do you find the clothes to revolutionize your style? 

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Where to Find Your Style 

The main reason a lot of guys in their 20s don’t dress as well as we possibly can is because of two reasons. One is that the steep prices of clothes make it seem not worth it to invest in something like a suit that will cost at least $200. The other is that a lot of guys just don’t know what to wear so we just default to what’s most available. So how can we fix these problems, and where is it that you can find your style?

If price is your problem, then the go-to answer is the thrift store. Thrift stores allow us to find decent clothes without breaking the bank. Chances are there are several thrift stores within a few miles of where you are right now, and if you know what to look for, then you can get your hands on something decent for less!

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Chances are, you have one of these thrift stores near you:

• Goodwill
• Plato’s Closet
• The Salvation Army
• Other Community-specific thrift centers

Thrifting can be difficult because you’re never sure if the location will have what you're looking for in your size or not. This is a reason why expert thrifters recommend always hitting multiple shops when you’re on the hunt for a certain article of clothing. Thrift stores may be unpredictable in terms of their inventory, but if you’re hitting multiple stores, then the chances are high that at least one of them will have a version of what you’re looking for.

Another way to find inexpensive clothes is to find knockoff brands of famous lines. If there is a piece of designer clothing you like, then chances are there will be plenty of knockoffs for a fraction of the price on sites like Temu or Shein. Designer clothing is often much more expensive than it needs to be, so investing in it is not recommended unless you have the funds for it. Sure, it may be nice to have the official designer version, but a lot of the time that piece of designer clothing is something like a white t-shirt that is nearly indistinguishable from one you can get at Walmart.

If your problem is instead that you really just don’t know what to wear, the easiest way to fix that is to copy other people. Yep, I mean it. Go on Google or social media and find an outfit that you like, then take a trip to a couple of thrift stores and see how close you can get to your reference. Chances are you won’t be able to replicate it exactly, but using a reference can help you find the colors and accessories that work for you.

Also, if you don’t know what to wear as a man, then go with the basics. You can’t go wrong with a T-shirt and some jeans for a casual outfit, and a button-down and some slacks for your business casual. Then just add a blazer to that for your business professional. As a young man, your wardrobe does not need to be complicated, you just need to put a little thought into your day-to-day outfits in order to show the world your merit.

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How You Should Dress in Your 20s

As a man in your twenties, you’re entering the prime of your life. You’re developing your identity, having fun, going wild, and learning lessons that will stick with you for the rest of your life. Your style should reflect this as well. You don’t have to go all out with your everyday outfits, but putting some thought into how you look can increase your merit and your confidence.

Dressing well doesn't have to be expensive either. With plenty of thrift stores all around us, it’s not hard to find the fits you need at a fraction of the price of designer clothes.

So if you’re looking to improve your style and dress better as a man in your 20s, here’s the scoop. Now you can stand out in the crowd and endeavor forward as a new, more fashionable man. 

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