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.
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
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
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
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
More Men’s Shorts Style Stories from SG HQ:
What to Wear with Linen Shorts
The Best 5″ Shorts (Updated for 2025!)
