Men have been wearing short, fitted shorts for decades, and that’s not changing anytime soon.
A few years ago, I wrote an article called How to Wear Shorts. In this article, I told guys to avoid wearing baggy shorts that go past their knees.
I thought it was pretty good advice. Nothing too controversial, right?
Wrong.
This post became some sort of troll mecca. In short order, the comments section was flooded with “real” (fragile) self-proclaimed alpha males saying things like:
I won’t even show you the worst comments – those have been deleted – but it’s safe to say that my advice struck a nerve.
Anyway…the point if this post isn’t to define what a “real man” is or isn’t. That would be impossible.
Instead, I’m putting to rest, once and for all, the notion that men shouldn’t wear short and/or fitted shorts.
They absolutely can and probably should.
Men Who Wear Short Shorts
In no particular order…
James Bond
This entire article could be summarized with one photo:
Connery (arguably the best Bond) is wearing shorts so short, they’re practically a Speedo.
Still not convinced?
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You might be thinking, “well what if I’m not ripped like Daniel Craig?”
Glad you asked…
Bob Marley
Did you know Bob Marley was into socc–I mean, football?
It’s true. And when it was warm outside, he opted for short shorts:
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It just goes to show, you don’t need massive muscles to pull off shorter shorts.
Conor McGregor
This MMA legend rocks short shorts inside and outside the octagon.
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In fact, you’d be hard pressed to find a photo of “The Notorious” wearing shorts that go anywhere near the top of his deadly knee caps.
John F. Kennedy
One of youngest, coolest and most popular U.S. presidents loved showing some thigh while he went sailing with his wife, Jackie.
Jacqueline Bouvier sailing with her fiancé, John F. Kennedy, Cape Cod, Massachusetts, 1953. Photo by Hy Peskin, [1039 × 1164] from HistoryPorn
Long sleeve shirt, short shorts, no shoes = effortless style.
John F. Kennedy Jr.
Apparently effortless style runs in the family because JKF Jr. always looked fresh.
In this pic he wore short swim trunks, a white tee with contrast ribbing, and old school Nike Killshots.
Perfection.
Larry Bird
The one and only “Larry Legend” fist bumping Magic Johnson is a show of sportsmanship, both wearing short that hit above mid thigh.
Los Angeles Lakers Magic Johnson fist bump with Boston Celtics Larry Bird, 1986 from OldSchoolCool
These guys were at the top of their game and knew a little something about function over form.
Michael Jordan
Speaking of basketball and short shorts, Il’l just leave this here:
If MJ preferred short shorts, so do I. Simple as that.
Kareem Abdul-Jabbar
Oh, and if you thought short shorts were just a weird 80s thing, here’s another basketball legend wearing even shorter shorts in the early 60s.
Lewis Alcindor, later Kareem Abdul-Jabbar, New York City, photograph by Richard Avedon, 1963 from OldSchoolCool
He’s even got a belt buckle on those bad boys. Nice!
Jackie Chan
There are a few guys on this list who could almost certainly kick your ass (and mine, probably simultaneously).
Jackie Chan is one of them.
Jackie Chan rocking short-shorts in the 1980’s from OldSchoolCool
The pink windbreaker and gold watch really complete this look. Bravo 👏🏼👏🏼
Tom Selleck
Magnum, P.I. himself, rocking his notoriously short chino shorts:
Tom Selleck and Morgan Fairchild on the set of Concrete Cowboys, don’t show Chandler this photo (1979) from OldSchoolCool
The tucked in polo is a nice touch! #modestmanapproved
Elton John
Sir Elton John in Los Angeles in 1986…notice the smaller sized watch too?
This just goes to show, you don’t have to be a professional athlete to wear shorter shorts. It’s all about your attitude!
Arnold, Franco & Sylvester
Look at these jacked strongmen showing off their hard work with some high cut shorts.
Arnold Schwarzenegger, Sylvester Stallone, Franco Colombo and a journalist, 1980’s from OldSchoolCool
I’d love to see an internet troll come out from behind his keyboard and insult Rambo to his face 👊🏻
This Navy Seal
Go tell this Navy Seal his shorts are too feminine.
Navy Seal shooting from an aircraft carrier. 1970’s from OldSchoolCool
But yeah, “real” men don’t wear tight shorts 🙄
This 70s Rollerskating Guy
I don’t who you are, guy, but I’d like to shake your hand.
His shorts are shorter than hers, and neither one of them seems to mind.
This Reddit User’s Dad
What a guy!
I bet his kids are awesome too.
These Tennis Legends
Two of the sports GOATs looking mean in the early 80s, back when men weren’t scared to show some thigh.
Try to insult McEnroe’s shorts and you’d get a swift racket to the face!
Another Tennis Legend
If you made a Venn diagram with sports and shorts, Andre Aggasi would be right in the middle, rocking a pair of high cut stonewashed jorts.
Andre Aggasi sporting stonewashed jorts in 1988 from OldSchoolCool
What a legend! By the way, his autobiography is worth reading.
David Mcintosh
This British model/bodybuilder/TV personality loves showing off his m a s s i v e thighs.
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Can you blame him?
Cristiano Ronaldo
Ronaldo, one of the greatest footballers of all time, is no stranger to short shorts, on and off the field.
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He’s not exactly jacked (although definitely lean), which goes to show that short shorts look good on thin guys too.
Demetrious Johnson
He’s one of the best pound for pound mixed martial arts fighters in the world.
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He’s not afraid of trolls, and he’s certainly not afraid to show some thigh.
David Goggins
Let’s just round out this list with one of the most traditionally masculine men in the public’s eye today, tough guy David Goggins:
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You can’t hurt him, and you definitely can’t hurt his feelings by making fun of his clothes.
Who wears short shorts? 🙋🏻♂️
Next time you hear someone say something stupid like “short shorts are for women” just send them a link to this post.
From pro athletes and movie stars to elite soldiers and regular guys, short shorts have been a go-to wardrobe staple for decades.
Do you wear them? Share your thoughts in the comments below!
Fantastic article! Short shorts are also part of the rugged traditional dress of some high alpine cultures in Europe (for example, the native dress of Tirol sometimes includes them). So for the haters, I don’t recommend telling a guy who climbs alps everyday, and keeps up his traditional lifestyle in the face of modern society, that his leather short shorts are anything other than rugged and masculine. 😉