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Want to Impress Women? Skip the Shirtless Selfie and Wear Shorts with Tall Socks

Increase your sock appeal
man wearing a t-shirt, shorts, tall orange socks and orange sneakers, set against a wavy blue background

by Megan Collins Updated: June 4, 2025

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There’s a new (old) men’s trend emerging for warm weather season, and it’s got me tapping “like” on Instagram ‘fit pics faster than you can say summer fling. I’m talking about the return of men rocking a tall socks with shorts outfit.

stylish man wearing a striped shirt, olive green overshirt, dark shorts, tall socks, and canvas sneakers
@goralfootwear
man in white t-shirt and shorts with tall socks and sporty sneakers
image: @ryanjh7
man smiling, wearing a yellow bucket hat, white t-shirt, green shorts, and tall socks with Vans sneakers
image: @triplepape_
man sitting at an outdoor cafe drinking a coffee and wearing a grey sweatshirt, shorts, and white sneakers with tall socks
image: @alexxwalther
man wearing tall socks with shorts, standing in a kitchen
image: @1lrg

Sock Appeal

Feeling style whiplash? It’s understandable. You probably have a drawer stuffed with no-show socks —maybe half of which actually stay up over your heels when you wear them — because that’s what you’ve been told looks good.

And it does! Women love to see a man flash some ankle bone when he’s sporting shorts.

But what once was a trend reserved for surfers and skaters — complete with Vans sneakers and board shorts — has now grown up. Today, wearing a tall socks with shorts outfit looks decidedly modern, and doesn’t require you to have ever mounted a surfboard or skateboard, even for a lesson.

Today, the combo of tall socks with shorts makes for a playful juxtaposition of casual and dressed-up, with a hint of rebellion against the grown man’s typical spring and summer uniform.

Styling tips for wearing tall socks with shorts outfits for men

@rrrampaa

Shorter Shorts, Taller Socks: Keep the shorts on the shorter side. Think: chinos or well-fitting athletic shorts that hit mid-thigh.

RELATED: The Best 5″ Shorts for Guys

On your feet, opt for calf-height socks. Nothing higher, you’re not a child prince.

Or, if you’re on the shorter side, snag yourself a pair of “half-calf” socks, which are, you guessed it, taller than a quarter-height or ankle sock, but shorter than a calf-height sock. They’ll showcase your legs for a more balanced look without overwhelming your calves in a tall socks with shorts outfit.

Sock Style: A neutral-colored crew sock always looks good. You truly can’t go wrong with white, but don’t be afraid to experiment with colors and patterns which add fun visual interest.

What kind of shoes to wear with a tall socks with shorts outfit

Obviously flip flops are out, but you’ve got more options than just sneakers when it comes to tall socks and shorts. Keep scrolling for outfit inspiration.

Tall socks with Birkenstock clogs

image of a man wearing a navy t-shirt, green drawstring shorts, tall white socks and brown Birkenstock clogs
image: @kennth_sylvester
man sitting on a bench outside wearing a baseball hat, white t-shirt, shorts, and tall socks with birkenstock clogs
image: @ethan_kieffer

Why yes, we’re still wearing Birkenstock clogs in 2025. And now, we (well, you) are wearing them with shorts (well, hopefully).

The key here is to find a balance. Keep the shorts clean-cut and tailored – think chinos or well-fitting athletic shorts. For the socks, a white sock that’s not overly athletic looks best.

Tall socks with black loafers

man wearing a tall socks with shorts outfit
image: @isaachudson
man wearing a tall socks with shorts outfit
image: @juliusgod

Granted, this look takes a good amount of confidence to pull off. A guy who can rock a quirky style choice like loafers and socks with shorts with self-assured swagger has to believe in his ability to tackle a trend. It shows he’s comfortable in his own skin, which is very attractive.

Shop men’s tall socks

Shop men’s half-calf socks – best for shorter guys

close-up of man's feet in suede Birkenstock clogs and calf-height socks, next to an image of a 4-pack of the same socks
Bombas Men’s Solids Half Calf Sock 4-Pack, $53 | shop on Bombas

More Men’s Shorts Style Stories from SG HQ:


What to Wear with Linen Shorts

3 Drawstring Shorts Outfits

The Best 5″ Shorts (Updated for 2025!)

Megan Collins

I started Style Girlfriend to help guys look, feel, and act their best.

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