The 21 Most Stylish Guys, 21 and Under

Its easy to read the GQ's and Esquire's of the world with the most stylish men in the world in them. What's not so easy to find is to find the guys that you can go to for style inspiration (the kind you need on a daily basis) from our generation. Sometimes you just need someone who looks like you (age wise) to go to for some guidance, you know?

After hours of research and analyzing street style photos, we've gathered some of the most stylish men under 21 years old to make your life easier. This is not a list of the celebrities with the most expensive clothes, but a plethora of bloggers, models, and athletes who's closets we'd walk far and long to get a piece of. 

Harry Styles

Images:  Vogue and Oyser Colored Velvet

This list isn't made any particular order and isn't a 'rankings' list, but this guy's first for a reason. The one direction star has the type of style that can be used if you want to be a rock star for a day, or turned into "NY Fashionisto" by replacing the KISS shirt with a V-neck and getting rid of the tattoos. We don't recommend copying outfits, but if you copy either of these we won't be mad at ya'. 


Jaden Smith

Image: Just Jared

Image: Just Jared

Get your pen and paper out. Now write two words: Go Monochromatic. One of the coolest ways to look cool without trying is wearing all black. If you google "Jaden Smith" you'll mostly find him wearing all black, yet he's considered one of the most stylish young celebrities even by GQ...see how easy it is?

Moral of the story: Wear all black if you want to be in GQ.

Nolan Gould

Image: Zimbio

Image: Zimbio

The Modern Family star is always red carpet ready, and that's why he caught our attention. Whether Nolan's wearing a tux or a floral shirt and jeans, he's someone you can look up to when it comes to formal occasions. Doesn't everyone wear those cheap black tuxedos to prom?

Devin Booker

Image: Fox Sports

Image: Fox Sports

Suit goals: dress like NBA rookie Devin Booker did on draft night, every night.

Justice Winslow

Image: GQ

When GQ creative director Jim Moore serves as your stylist for draft night, that means something. If you checkout Justice's Instagram (@Iamjustice) you won't be disappointed by his casual off-duty style. Your one takeaway from Winslow's style is the light blue suit, which is one of the most stylish statements you can make. Get away from navy, its getting more boring as the seconds pass.

Jovany Perez

Image: Upscale Hype

After forming "The Young Crafters" with Diggy Simmons, this young entrepreneur caught the attention of many in the fashion world. If street style's your thing then this is dedicated to you. If you're partnering with Diggy Simmons for a collaboration then you're doing something(s) right.

Lucky Blue Smith

Simplicity and superb fit. Those are the words that describe Lucky Blue Smith's style; and yes, that is his real name. He's killing the fashion game right now by keeping it simple, and any picture you'll find him in is a good starting point for anyone just getting serious about their style. With 1.3 million followers on Instagram, even his feed proves that it doesn't take a lot to say a lot when it comes to your style. 

Justin Bieber

Who would've known that JB and the word "GQ" would go together? Well he looks pretty GQ to us in this photo, especially with the non-navy suit (see the theme here?) with black shoes. If you checkout more of his style, you'll find some pretty decent contemporary street wear in his repertoire. Touché Mr. Bieber, touché.

Brooklyn Beckham

Brooklyn may not have invented the tee shirt and blazer look, but we might have to do some extra research based on this shot. Just like his dad, Brooklyn always looks effortless whether he's in a tux, or wearing a casual dinner/coffee date look the second outfit.

Don't forget the signature smirk, your best accessory.

Romeo James Beckham


Image: Star Kiddo

He starred in Burberry's first Christmas Campaign, so it's safe to say the 'the little bro' belongs on this list too. A few style secrets from Romeo are to

1) Don't be afraid to pair a scarf with a suit. It'll be one of the classiest moves you make in your life.

2) Don't be afraid of a pop of color down low. This young man wore pink sneakers, PINK sneakers, and it looks amazing.

Igee Okafor


You may have caught him at New York Fashion Week: Men's, and if you didn't then I can tell you that you missed out on meeting one stylish guy. Igee Okafor is a menswear blogger, currently in enrolled in school in New York. Over on his blog you'll find him wearing dapper combinations along with casual looks that are perfect for a Sunday brunch (of many occasions).

Dean (aka ProperKidProbs)

After starting his blog Proper Kid Problems before his first year of college, Dean has grown a site that raises the standard among our generation for both style and lifestyle. We need more people like Dean in the 21st century, and the evolution of his style and brand resembles his maturity at only 21 years old. This outfit with a sand desert boot and red jacket is a great way to stay 'preppy' while going outside of the box (or not having one at all).

J. Bradley

He loves his Jeep, rowing, and The Office. If you relate at all, get to know J. Bradley who started his brand J. Riley at an early age which advocates classic, American style. If you're a young man at sea or you're a fan of the preppy tradition, you can view his work at

Sunny Murthy

As an undergrad student studying Biochemistry, Sunny looks to inspire college students to dress their best despite their age. You can view his work at

Alonso Mateo

Image: Gilt

Image: Gilt

The kid on Instagram (@luisafere) that you're three times older than, but three times less stylish than.

Jalil Peraza

Image: Complex

The founder of Appeal Clothing and the Kanye Proto J who's making serious moves in style and fashion. Checkout this article to see what he's doing.

Diggy Simmons

Image: Hotel Fashion Land

Gio Serna - Menswear Blogger



Instagram: @RyanSecret

Collette Wixom


Instagram: @ministylehacker

Written by: 

DJ Hargrave (@tailormadedj)

Founder & Editor of College Style Guy