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Home / Blog / Clothing and Style

5 Easy Tips for Dressing Like an Adult (2023 Men’s Guide)

Published on April 6, 2020 by Eric Rodriguez · Clothing and Style May contain affiliate links (what's this?)

The other day I spotted a young couple in the subway. They appeared to be somewhere in their late 20s to early 30s.

Table of Contents

  • Upgrade Your Jeans and Shorts
  • Upgrade Your Footwear
  • Upgrade Your Shirt
  • Upgrade Your Headgear
  • Upgrade Your Backpack
  • Closing Thoughts

It was a beautiful Saturday afternoon, so I assumed they were spending the day together.

The young woman was smartly dressed in a wool turtleneck sweater, loose fitting knit trousers, modest heels and a nice handbag. A classy New York outfit perfect for brunch or lunch in a nice Manhattan bistro.

The young man, on the other hand, was wearing ill-fitting faded jeans, a red sweatshirt/long sleeve t-shirt with some type of graphic on it, running shoes, which have seen better days, and a multi-colored nylon backpack.

Couple holding hands
Source: Pinimg

“What’s wrong with how he was dressed?” you might say.

There’s nothing wrong per se with his outfit, but in comparison to his partner, he was dressed like your average 13 year old boy.

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How to Dress Well In Your 40s and 50s (and Beyond)

Don’t worry, it opens in a new window 😉

I believe the only time you could get way with dressing like a 13 year old is if that 13 year old is your son and it’s something like ”Father and Son Dress Alike Day.”

If not, then it’s definitely time to upgrade your wardrobe. If this sounds like you and you feel you’re ready to start dressing like a mature man, then keep reading.

Here are 5 simple things you can do to elevate your look from frat boy to a stylish adult.

Upgrade Your Jeans and Shorts

For a long time I wore jeans practically every single day. Truth be told, they were the only pair I had. Sound familiar? Lots of guys wear nothing but jeans, sweatpants and in the summer, shorts.

Example of summer clothes that need improvement
Source: Flickr

Now there’s nothing wrong with jeans or shorts, as long as those jeans are not worn out, full of holes and bunched up at the ankles.

Baggy jeans
Source: Flickr

A nice pair of tailored, dark wash jeans will go a long way.

Perfect cuffed jeans

Want to bring it up a notch? Try a nice pair of chinos. In the winter, throw on a pair of wool trousers and in the summer, a pair of linen pants are perfect.

Short sleeve button up and chinos

These upgrades are very simple and easily elevate your look from frat boy to mature man.

Oh, and please leave the sweatpants for the gym. 😉

Upgrade Your Footwear

Men love to wear sneakers. Heck, some of us wear them way after they should have been tossed out.

Now I’m not saying you need to completely stop wearing sneakers, but unless you’re trying to look like Steve Jobs, leave the running shoes for the track and switch them out for a pair of simple minimalist sneakers.

Something like Greats’ Royale, Koio’s Capris, or any other type of minimalist style sneakers, preferably in white or black.

Cuffed chinos with white sneakers

Want to bring it up a notch? Switch to a pair of comfortable Chukka boots or loafers.

Jeans with chukka boots
Source: @ericrnycstyle

Both work well with a pair of jeans, while giving you a more stylish look.

Upgrade Your Shirt

I get it, you’re a Marvel or Star Wars fan and you want everyone to know. Hey, I’m a fan, too, but let’s leave the graphic t-shirts for when you’re attending Comicon.

Aeropostale store

It’s time to move away from those graphic t-shirts and move on to something more mature. Think collar and buttons. An Oxford Cloth Button Down (OCBD) shirt is perfect.

Button up shirt with jeans and leather loafers
Source: @ericrnycstyle

The OCBD goes great with everything from jeans to chinos. It looks great with the sleeves rolled up for a lazy Sunday brunch look or with a tie and blazer for a bit more sophisticated look.

If that’s moving too fast for you, try a polo shirt or even a henley.

Leather motorcycle jacket with jeans and henley
Source: @ericrnycstyle

Think of these two as the more stylish version of the t-shirt. You get the same feel as a t-shirt, but the addition of a collar and/or some buttons and you now have a more stylish look.

Upgrade Your Headgear

One piece of clothing that I feel definitely gives a man a more juvenile appearance is a baseball cap, even more so when worn backwards.

Baseball cap worn backwards
Source: Wikimedia

To elevate your look, replace the baseball cap for a stylish flat cap. Is there anyone more stylish or bad ass than Thomas Shelby from “Peaky Blinders?”

Flat cap and wool jacket
Source: @ericrnycstyle

Want to turn it up a notch further? Try a fedora. The right fedora can give you that sophisticated Don Draper from “Mad Men” look or, if you’re really daring, that rock and roll look of Johnny Depp.

Fedora and topcoat

If you’re just not quite ready to get rid of the baseball cap altogether, stick with a simple solid color baseball cap with either no graphics or very minimalist graphics.

Plain baseball cap
Source: Lululemon

And for Goodness sakes, whatever you do, do not wear it sideways or backwards. This screams frat boy or 80s rapper.

Upgrade Your Backpack

Personally, I haven’t used a backpack since my college days.

Kid with big backpack
Source: Peakpx

My bag of choice, until about a year ago, was a leather messenger bag. A messenger bag, whether leather or canvas, gives you more of an adult look.

It’s also easier to wear on those days when you’re wearing a blazer. A nice leather bag, preferably with a removable shoulder strap, works well in and out of the office, too.

Now if you prefer a backpack, look for something with a clean, minimalist design. Avoid nylon backpacks with multiple zippers and go for something cleaner, like Aer’s Day Pack or Carl Friedrik’s Bowen Backpack.

Sleek black backpack
Source: Squarespace

Both are simple, yet very stylish choices.

Rugged leather backpack
Source: @ericrnycstyle

Aer is better for minimal, streetwear type aesthetics, while Carl Friedrick is great for rugged, preppy and refined looks.

Closing Thoughts

So basically, that’s all it takes to upgrade your look. Now you may say, “I like the way I dress” or “My wife/girlfriend has no problem with the way I dress.”

Well, that’s fine. My intention is not to make you feel bad about how you dress or mock you in any way, but I can tell you that once you do decide to upgrade your look, things will change.

So go ahead and implement these 5 simple changes into your wardrobe today and see how simple it is to go from frat boy to stylish adult.

Welcome to adulthood.

Clothing and Style backpack, Men's Jeans, style

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About Eric Rodriguez

Eric is a Brooklyn-based male model and men's fashion enthusiast who enjoys writing about boots, hats and everything in between. You can follow Eric on Instagram.

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  1. George E Givens Jr says

    April 18, 2020 at 5:13 am

    Hi Brock,
    Enjoyed the article and as usual have something to say :-).
    First, sorry I’m so late getting to it. I recently lost my father-in-law and then Covid-19 restrictions came etc., etc.
    I whole heartedly agree with losing the tattered jean look. I’ve noticed even older guys are wearing them, ugh! I use some of the wardrobe apps like Able Style, Lookastic.com and Dress Right. Almost every other casual suggestion is a ripped jean! Also not a fan of the really skinny jeans or the crop pants (don’t care that Dwayne Wade wears them) either. Especially for guys over 35.
    However, I disagree a little about the sweatpant. Have you seen the new “everyday” pant like the Ace or Radius pants by Mack Weldon? I own both and if I have no where important to be I practically live in them (especially the Ace) in spring, early summer, and fall. They look great and feel even better.
    Additionally, I’ve become a fan of the Henley shirt, long and short sleeve, heavyweight and lightweight. They’re very versatile and comfortable.
    Finally, even though I’m an OG (old guy (69) not old gangster) I am a fan of the superhero, Star Trek and Star Wars tee. At the beginning of the Marvel and DC movie series my wife gifted me a complete set! So I must admit in warm weather if I don’t have to be anywhere I wear them almost everyday. Sometimes I even wear in winter over a long sleeve tee, like Sheldon on “The Big Bang” TV show. Believe it or not my wife loves me to wear them. Now that they’re a few years old they look even better than when new :-).
    Stay safe and well.
    Best Regards,
    GEGJr aka OG

    Reply
  2. Dirk says

    April 7, 2020 at 11:36 am

    I like this blog even though I am 6 ft tall and not a modest man 🙂 Some years back Robert Bly wrote a book entitled “The Sibling Society” which detailed the phenomenon of a world without adults, and he touched on men dressing like boys.

    Reply
  3. Roman says

    April 6, 2020 at 6:00 pm

    Hi
    Excellent and informative article, thank you. Your headline about seeing men around dressing up as boys is so true, with some men not making much effort in the same way as some of the ladies do. We have an overall similar culture here in New Zealand, although things are slowly changing for the good in the way some men are responding to the men’s clothing we design and offer in ours menswear shop. The other things I would like to mention please, encourage men of all ages to add some quality, colorful button up shirts in their wardrobe with interesting shapes and patterns. So overall, lets get men out there to wear some more color, not only just the classic basic greys, blues etc. and combine these with good quality fitted smart casual shorts.
    Your male model in this article is spot on, an excellent model, current looking and very inspiring to look at.
    Thanks
    Regards
    Roman

    Reply

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