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How To Dress In Your 20s – Young Men’s Style Tips With Outfit Ideas

Fashion, Men's Style Guides
Thursday, 8th February, 2024

How To Dress In Your 20's - A Men's Style Guide

When it comes to picking out what to wear in your 20s, it can be tricky for guys.

But being a well dressed man when you’re young can be a lot of fun too. If you want to dress attractive, there’s certain things you need to do well.

Whether it’s the younger end where you’ll probably be at Uni or just leaving or starting your first job or moving up in the world.

Your twenties is definitely one of the biggest transitional phases in your life.

With that said, how do you dress in your 20s, and what do you wear?

Fortunately, there’s plenty on offer when it comes to young men’s fashion.

Young Men’s Style: Quick Takeaways

What You Should Do

  • Always dress For The Occasion
  • Wear what you feel comfortable in
  • The fit is everything
  • Remember the basic, staple clothes
  • Don’t be afraid to make mistakes

What You Should Avoid

  • Over dressing is as bad as under dressing.
  • Buying too many cheap clothes to fill your wardrobe
  • Using too many colours in your outfits
  • Not wearing formal or semi-formal clothes when the occasions dictates

First up, we’ll go through some of the style rules and advice you should be following. Then on to the pieces of clothing that you can consider.

It’s Time To Experiment With Clothing

When it comes to nailing down your own personal style, your twenties is going to be the age when you can experiment.

You should have more money than in your teens, and you’ll probably not have huge financial commitments. So spending money on your wears is something you can do.

There’ll be a ton of different occasions where you need to dress appropriately and differently.

From wearing a suit to an event, to wearing smart casual, and then something when you just want to chill. There’s a lot of things to think about when it comes to your own personal style;

Are you more of a punk grunge kind of guy? Do you prefer the rock or indie look with leather jacket? Do you like the idea of streewear and oversized clothing, or do you just want to keep things smart?

You can be all of the above in your 20’s, it’s the time to find out what you like best.

The Fit Is Key To Looking Good

Getting The Best Fit For Your Clothing

The usual number one rule always applies, the fit is key.

If you’re trying out certain trends the fit is less important, as it’s more about that trend. But more often than not, having the right fit of clothing is the way to go.

It will also save you money in the long run when you discover that this is a golden rule which you’ll definitely follow later in life.

It’s easy to get the fit right if you dress for your body type. This is an easy hack to looking good in most clothes.

Look For Style Inspiration

You probably already look for inspiration in fashion without even knowing it. Of course Michael 84 is a men’s fashion blog, so you’re off to a good start!

You can see what people are wearing on the street, in film or on TV, and think that’s a good look.

You can take inspiration from other guys, incorporate it into your look and add your own personal touch to it.

Get On Trend

Get on trend - Read men's fashion blogs for the latest brands and style advice

If there’s one thing you want to do with fashion in your 20s, it’s being cool which means being on trend.

This is usually done with brands, logos and whatever is cool at the moment. I think this is perfectly fine and natural when you’re younger.

If there’s one time in your life when you’re going to rock huge graphic or slogan tees, this is the time.

Mix Up Your Style With Classic Staples

A Leather jacket, white t shirt and dark pair of denim jeans

Wearing a leather jacket and white t-shirt. An easy to pull off look with timeless style.

You’ve heard the phrase stick to the classics. They’re classic for a reason, and when it comes to menswear, we’re talking about timeless classic pieces or colours.

A good pair of dark denim jeans, a white shirt, a leather jacket. These are just 3 examples of clothing which will not go out of style.

You can mix up your new trends with a classic piece of clothing.

This could be combining a new style of shirt or T-shirt with a pair of denim, or pairing something such as white jeans with another wardrobe classic.

Making Mistakes With Fashion

Don't be afraid to make mistakes with your style

This hoodie was one of the worst purchases I made in my 20’s when it comes to clothing.

We all make mistakes when it comes to fashion, especially when buying new things.

This is a good thing, because it means you’re trying new things. You’ll not get it right every time, but that’s normal. This is the perfect time to experiment with your style, and you will get it wrong.

I’ve talked about the worst fashion purchase I made which was in my 20’s, who remembers that Ed Hardy craze… 😉

Think Of Dressing For Your Lifestyle

Do you go clubbing a lot? Or are you going to the theatre a lot? Or maybe it’s both.

When you’re buying your clothes, think of the occasions which you’d wear them.

Too many times we all just go out and buy lots of clothes without thinking about when we’d actually wear them. Then we end up having a wardrobe full of stuff we don’t wear.

Wardrobe Essentials & Casual Outfit Ideas For Men In Their 20’s

Here are the must have items which you should have in your wardrobe in your 20’s, by the time you’re entering your 30’s, these should be checked off your list.

Your First Suit

Get Your First Suit In Your 20s

Job interviews, going to work, Christenings and plenty of other occasions, there’s going to be a time where you need a suit.

Getting your first suit in your early 20s is such a good idea. As already covered, the most important rule is the fit, so get one which fits you well.

Second is fabric. A 100% wool suit should be bought, which you can get for a variety of prices, depending on your budget.

I’ve talked about your first suit and colours before, and you may be thinking a black suit is the colour to go for.

But as we’ve already discussed, grey and blue hues, especially colours like charcoal and navy are better options for a first suit.

They are more versatile, and can be worn everywhere.

T Shirts

White t-shirts are easy style choices for men in their 20s

Wearing a plain white t-shirt in summer is a good casual choice.

T Shirts, T Shirts, everywhere. You’ll spend most of your money, and most of your time, buying T Shirts. They are the ultimate in any casual outfit, and can be dressed up as well as down.

Hopping on to trends and wearing the latest brands is going to be something you’re likely to do, and that’s OK.

Plain white T Shirts are of course timeless, and can be a good investment, but you can also buy seasonal logo tees from your favourite brands and designers.

If there’s one point in your life when you’re going to drop serious cash on one designer t-shirt, it’s in your 20s.

Dark Denim Jeans

The most versatile pair of jeans, dark denim can be worn casually, and in a smart casual setting too.

When you don’t want to wear trousers, dark blue or black jeans are there to save you, keeping you looking smart.

Always remember to get the fit of denim correct, so they always look good on you.


If you feel you’re too young to wear formal trousers for your day to day wears without a suit (unless your work uniform dictates it), the go to trousers are the informal kind. chinos.

The cotton twill pants are the perfect go to option when you want a change from jeans and need a smart edge.

Hoodie & Sweatshirts

Sweats such as hoodies and sweatshirts can become part of a laid back casual look for you in your twenties when you’re out and about.

They’re perfect to wear for relaxing in the house for any age, but are particularly trendy with younger 20-somethings.

From going to Uni to going to the Gym, they’re items which never look out of place.

For a contemporary look you can go for a plain colour sweatshirt. A hoodie is more casual, and a zip up can be used as a light jacket and layered with a tee for a relaxed look.

White Shirts & Upping Your Shirt Game

Wearing a white shirt with a blazer

You’ll want to up your shirt game for smart occasions.

The classic white shirt can be worn in any environment when you need to look a bit more dapper than usual, and can be worn with almost anything.

You should be looking to wear more than one colour and give yourself some options.

Navy and black are great colours, adding in a sky blue shirt which can be interchangeable with the white shirt is another good idea.

Check and other patterns are also good options for when you want to add a bit of edge to a smarter look.

Edgy Clothing

If you want some edgy clothing style, you can’t look past a good leather jacket.

A leather jacket is timeless, and is going to be in your wardrobe for a long time. If you’re into this look, it could be considered an investment piece.

But if you’re just looking to try out the style for an outfit, you could get away with faux leather or pleather.

It’s cheaper, and if you really embrace the look, can upgrade to a better quality real leather jacket.

A Blazer Or Smart Jacket

There’ll be a time where you need to wear a jacket in a smart or smart-casual setting, it gets cold a lot here in the UK.

A perfect go to jacket is a plain and simple blazer.

If you’ve got yourself a suit as suggested above, and it’s navy or charcoal, you can wear the jacket without the trousers. This creates a ‘separates’ look, using just the jacket as a blazer.

A Bomber Or Casual Jacket

Bomber Jacket

I think the most perfect casual jacket for men in the vast majority of situations is a good bomber jacket.

I have plenty of them, and love to wear them.

Picking out one in a staple colour such as blue, grey or black will mean it will go with pretty much everything else in your wardrobe, keeping you warm as well as looking good.

Smart Shoes

Wearing smart shoes as man in his 20s

When I’m talking about smart shoes, I’m talking about either the Oxford or Derby style. These are shoes which can be worn for the most occasions, and you’ll want a fairly good pair to last a while.

Owning at least 1 pair of smart shoes is a must when you’re in your 20’s. (here’s how many shoes you need to own)

Wearing them to work, on a night out, to formal occasions and even informal occasions, a good pair of smart shoes will serve you well.

You can get yourself a nice pair of black, brown or tan shoes, or if your budget can take it, get at least 2 different colours.

You don’t have to spend a fortune on a traditional shoemaker just yet, that can come later in life.

White Trainers

Men's Summer Style - All White Trainers

Wearing all white Nike Air Max trainers with black denim jeans

For your Summer, or even for just a casual pair of trainers, a good pair of white trainers is something you’ll want to be wearing in your 20’s.

They are always stylish and can be worn with a series of outfits, and will not go out of style during your decade of having fun. Just make sure you keep them clean.

A Reasonable Watch

Get A Decent Watch In Your 20's - Men's Style

Wearing a watch adds some sophistication to your outfit

There’s just something gentlemanly about watches, and are one of the few accessories men actually have available to wear.

I say a reasonable watch, as there’s some serious money which can be spent on watches.

Save the money until you’re in your 30s, when you’ll appreciate the heritage and tradition of timepieces.

Until then, a nice clean minimal watch is not only an understated style piece, but very fashionable at the moment.

There’s plenty of reasons to wear a watch, and starting in your 20’s is a good time. It will add something extra to any outfit you’re wearing.

Style Rules To Follow In Your 20’s

  • Experiment with trends to find your signature style
  • Buy a good pair of smart shoes
  • Buy casual clothing items such as T-shirts, sweatshirts and jeans
  • Invest in your first suit
  • Dark jeans are your friend
  • Blazers will add an element of class to a smart casual outfit
  • Have fun with your outfits

After your 20’s

After your 20’s comes your 30s. By this time you should know what direction you want to take your personal style in, what you like and don’t, and what works best in your life.

You may have already began to invest in good quality clothing, and you’ll want to do that even more, investing more in your own personal style.

Check out the what to wear in your 30’s style guide when you’re ready to enter the more mature years.


Dressing in your 20’s should be fun.

It’s a great time to experiment with different styles, and decide what works for you, and what you like.

It’s a time where you can experiment, wear super casual clothing as well as something a lot smarter.

It’s also a good time to spend disposable cash on clothes, so later in life you’ll not end up wasting money on menswear you’ve already discovered isn’t for you.

You can of course read a lot more on fashion tips if you’ve got some pieces in your wardrobe and want to know what to wear or how to style them.

Michael Adams

About Michael

Michael Adams is the founder and editor of Michael 84, blogger from Newcastle, UK. Sharing men's fashion tips, style advice and lifestyle information for all guys.

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