6 raw tips for guys! How to dress in your late 20

Time to MAN UP
how to dress late 20s

Wondering how to dress in your late 20 as a guy? You’ve come to the right place!

Admit it, the adolescent period for us guys doesn’t do much of a change. Our late 20s age period is when all significant physical and mental changes occur.

All those working so hard, partying even harder, drinking, and vices all come together, making our once teenage figure into a mess.

Then we put workouts and diet as our answer to restore our body figure in order.

The question is, can your time allow you to do such? In fact, these solutions will take a lot of time for us to see results and be presentable once again.

Yet there is one faster and proven effective solution to make us look great in no time, regardless of your current daily routine. It’s none other than fashion.

Dressing up appropriately in our late 20s age.

Here’s a guideline about how to dress in your late 20s for guys.

  • Fit matters; consider your current body type.
  • Long-term Wardrobe investment instead of a short-term fashion statement
  • Neutral Colors are now your best friend
  • Prioritize comfort for your everyday life
  • Start investing in some good shoes
  • Be well dressed and not overly dressed.

1. What’s your current body type?

how to dress in your late 20 guys
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Let’s talk about the most important of all here, the fit.

How to dress up appropriately. How not to look like a guy dressed like a boy or someone very uncomfortable just to look at.

A. How to dress in your late 20s for a scrawny body

If you have a scrawny body, wearing any T-shirt is fine.

When you’re in your late 20s and still wear one, don’t be surprised why people start calling you “a walking clothes hanger.”

Go for a henley instead of your regular tees.

Not only would it make you look mature, but it will also make you look sophisticated and neat.

It has the same feel as an ordinary T-shirt but looks more appropriate for your age now.

B. How to dress in your late 20s for a muscular figure

If you are muscular, stop stating the already obvious by always wearing a tank top. It looks very intimidating and somehow gross for the ladies.

You could go for either a relaxed fit or oversized clothing. Oversized because you want to give em’ ladies something to be curious about.

Hiding those ripped muscles you worked hard for is a great surprise underneath.

Relaxed fit for your comfort and for you to look less intimidating and clean looking.

As you walk or move with comfortable fit clothing, those muscles will do the talking for you, giving you a silhouette like a greek god.

C. How to dress in your late 20s for medium build guys

For medium build guys, especially those with ABS, “A Big Stomach”.

Choose clothes that are mostly fitted in the chest and loose down below.

It would create an illusion that you are well proportioned and not giving too much emphasis on your tummy looking like a man who’s about to give birth.

It also looks manly if you choose to clothe only fitted around the chest. A great example of this is Ribbed clothes.

It adds volume to your upper body and emphasizes the chest more.

Creating the illusion that you are packing more on the chest than on your belly.

MUST READ if you have a man’s boob: How to hide gynecomastia FOR REAL

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We are not that young anymore and still always want to wear what we see in the media, especially on the internet.

Not to mention, it is expensive for such a lifestyle. Late 20s guys should be more considering their financial security by now, starting with what they wear.

A. Denim

Go for clothing that never goes out in trend. Denim is our best friend for this. Especially our jeans. We guys love our jeans, which last a very long time.

Consider buying quality types of denim. Go for brands that are proven to last for ages. But hey, it doesn’t mean you should go for an expensive brand!

There are a lot of reputable brands in denim items of clothing that provide high-quality clothing.

Denim jackets, vests, a couple of jeans, a denim polo, perhaps? These are types of denim that can be easily paired with one another without any problem at all.

Also, in general, dark hues denim looks way more sophisticated than light-washed ones.

B. Leather

Leather is also one type of timeless fashion for us guys. Consider having one as well.

Many guys focus on the shoes but hey, let’s not forget a rusty leather jacket can look irresistibly masculine.

C. Turtlenecks

Turtlenecks are here to stay, so why not grab some for your wardrobe?

High-neck tops can always make you appear to be slightly more polished and intelligent – I mean, who doesn’t want that?

D. Blazers

Most importantly, invest in some formal clothes. Specifically blazers.

Blazers can be worn for either formal or casual compared to your standard coat. It also blends well with most common getups for us guys giving us this instant gentleman appeal.

If you are in your late 20s, I SERIOUSLY suggest you get your blazer tailored. Trust me, the difference is real.

3. The right color choice

Loud and vibrant colors sure are fun to look at. Sure, if you are a teenager.

But if you want to look more mature, and well-mannered looking, go for neutral colors.

These neutral colors are perfect for men, even beyond their late 20s. There are the colors:

  • Navy Blue or Lighter Blue
  • White
  • Cream
  • Khaki or British Khaki
  • Beige or Off white
  • All shades of Gray
  • Black
  • Olive Green

These colors are very versatile and very manly for us guys. Versatile, as you can use this on any occasion or any activity.

Looking like a well and properly-groomed man whenever and wherever the time calls you for.


Do you know ladies LOVE men wearing dusty pink? Feel free to team a pink button-down with khaki shorts.

Thanks me later man.

4. Your wardrobe should fit your lifestyle

how to dress manly not a boy
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We will be sure to have different daily lives once we get to our late 20s. Our schedule and daily activities will hugely impact our fashion sense.

That is why most of our fellow men ignore fashion and call it a day with whatever.

Here’s some advice that may keep your looks right on track.

A. How to dress in your late 20s business guy

If you are more of a corporate guy and always on the go, fill your wardrobe with clothing that can still stand on its own, even if you put down that coat.

Turtle necks and henleys would be the ideal examples of these.

You can have an instant outfit for an after-work activity just by taking off your coat and letting any of these two do the work for you.

B. How to dress in sporty and classy in the late 20s

For the guys whose daily lives are filled with athletic activities or involve a lot of physical activities, consider sweatshirts and joggers.

Not only can you still look fresh after a long and tiring work/activity, but it also won’t restrict you from moving freely and relaxing those stressed muscles.

For a more appealing fashion sense, have some denim clothing to sport out those physiques even more.

C. How to dress sophisticated and approachable

And if you are more like a “Mr. Nice Guy.” Some sort of a writer, director, librarian, gamer, work-from-home dude, you know, the likes.

Transform yourselves from being a nerdy dude to a charming guy next door vibe.

Cardigans, scarves, stoles, and oversized white shirts will elevate your look into a lovely man.

If you are a hoodie guy, why not go for harem pants? Acquire that urban ninja looks and make yourself look excellent with every step.

You can also alternate your hoodie with a bucket hat to provide variation with your upcoming outfits.

5. Stepping forward to fashion by stepping with quality shoes

The late 20s is the point we should lie low with those Chuck Taylors and consider a different kind of perspective. Something to make us look more like men than average boys.

Leathers should be our main priority for stepping up. At least a pair of good leather that suits your personality will go a long way and also be a good investment.

Any formal occasion would not be a problem anymore once you had one.

This is the right time to invest in those nice kicks. It doesn’t have to be splurging and spending everything to the point you can’t.

A good brand with a very comfortable design is a great way to start.

Nike Air force one and Reebok Classics are great examples of this. They provide comfort and fashionable looks without breaking the bank.

Designs are also neutral making them easy to pair with any outfit.

6. How to dress maturely as a man? Balance

How to dress maturely male
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This saying is true even in fashion. You are a man, not a walking storage hook with a bunch of accessories.

Remember to always keep it simple, compact, and less.

Adding more means making it more complicated; outfits should not be.

Too much of this and that will make you look unpleasant and not neat, regardless of your good hygiene.

A razor doesn’t need anything else besides being sharp, and neither do you as a man. Simplicity makes you look slick, tidy, and sexy.

As for accessories, even modern celebrities tend to just wear two kinds of accessories most often. A watch and one single chain on the neck. That’s it.

Youngsters will find this ironic to still wear a watch since a smartphone has a clock. But in your late 20s, men should think better.

It is the point of our life where the statement “you’re not getting any younger” starts to linger within us. That is why we wear a watch to keep tabs on time.

Making sure everything goes along with the schedule with just a flick of the wrist. It is also an excellent way to flex our financial stability to others, depending on how much it costs.


Needless to say, engaging with men’s fashion and becoming a well-groomed man is simple and more straightforward than we might think before.

All this time, we only needed proper guidance and the motivation to be fashionably inclined.

Fashion doesn’t make us less of a man but makes us look more like one.

Considering your well-being and appearance is one mature way of showing instead of telling. Improve to a better version of yourself and know that age was not even a hindrance afterward.

Have you enjoyed our entry for How to dress in your 20s, guys? If you love this, high chance you will find the popular read below useful. MAN UP in all aspects dudes!

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