Fit Lesson 4: Shorts.

Posted on July 28, 2009 in Basic Fit Lessons, Body Type, Casual, Fit Lesson, Shorts.

I omitted shorts from my fit guide on pants, but that isn’t because they are unimportant, or that guys wear them correctly, it’s because they belong in a class all to themselves. Just like shoes, guys typically don’t put that much thought into a pair of shorts. They check to make sure they fit in the waist, they don’t ride up too high on the leg, and they’re done.

A lot of guys still revert to their college days where they can just throw on a pair of shorts, because it was all casual, all the time, and the super-sloppy look was cool and acceptable. Dressing like a grown-up means no more baggy shorts. That means ditch the ill-fitting wrinkly cargo shorts made famous by American Eagle and Abercrombie and Fitch (BTW, if you’ve graduated college you should not be anywhere near an A&F or their counterparts). Instead opt for well-tailored and clean shorts.

So, it’s time to update the way your shorts fit. Since you’re showing more skin off, shorts are particularly susceptible to look awkward based upon body type (more below).


As usual, we start with the biggest problem. Most guys wear their shorts waaaay too long. The killer is, that no matter what your body type, shorts that are way too long accentuates it. If you’re shorter, it makes you look like a midget. If you’re super tall, it makes you look too stretched out.

The shorts in #1 are almost halfway down his shin, making him look like a child. Whereas, #2 are above the knee and makes him look like a suburban dad.


Photo credit: iStock.

Photo credit: iStock.


Photo credit: Target.

Photo credit: Target.

The ideal short length for most guys will hit between halfway down the kneecap to just below the knee. Anything longer and you look like a midget. And anything shorter makes everybody around you uncomfortable, despite the recent urban trend of shorts that are well-above the knees. Shorts #3 hit just the right area of the knee.


Photo credit: Original Penguin.

Photo credit: Original Penguin.

Leg opening

Trim is the way to go. If you have chicken legs, too wide of leg openings will accentuate that, and make you look even more ridiculous. If you’re stocky, shorts that are too baggy make you look even more so. For just about everybody, baggy shorts make you look too sloppy. Notice how the shorts in #4 are way too large for the guy making him look goofy (it isn’t just the popped collar).


(cc) Photo credit: Malingering.

(cc) Photo credit: Malingering.

Since shorts are inherently casual, you don’t need them to be as slim as your pants, but you still want them to fit precisely. Like #5; much cleaner.


Photo credit: Urban Outfitters.

Photo credit: Urban Outfitters.

I used to think cargo shorts were the devil (despite admittedly owning a pair of baggy ones). It goes against the whole “don’t dress like an undergrad” mantra I’ve been espousing. But, I have recently come to appreciate the well-fitting cargo shorts. What you want to look for are the cargo shorts whose pockets don’t bulge out. They can still strike clean lines even with the additional pockets. See #6.


Photo credit: Banana Republic.

Photo credit: Banana Republic.

*A note for the bigger guys: OK, this is where the rules get a little bit bendy. If you’re a bigger guy (but not stocky), it is OK to wear shorts that are a little bit longer (just below the kneecap) and slightly baggier than for trimmer fellows. This gives you a little bit more room, and prevents you from looking like you shrunk your shorts and your junk is in a bind.

Cargo shorts help to add a bit more lines for the eye to look at, breaking up your profile and makes you appear a bit slimmer. BUT, don’t go crazy. You want to be comfortable but not swimming in your shorts. And if you do go with cargo shorts, still don’t get them with huge pockets, like dude #1.


No jean shorts. Just about everything else is fair game.

If you wear shoes that aren’t sandals with your shorts, wear no-show socks. This compliments the clean look, and does away with the ’90s gym attire vibe. Go for something like #7; just perfect..


Photo credit: Gap.

Photo credit: Gap.

3 Responses to “Fit Lesson 4: Shorts.”

  1. jc says:

    kudos on knocking the current short short trend for men. i can safely say, being a woman myself, we do not want to see that much thigh. can i ask, though, what brought this movement on men wearing short shorts?? fashion historians have been known to point out that women’s skirt lengths can be traced to times of war and peace (i.e. peace = shorter, war = longer). it would be interesting to see if there were any social similarities between this current trend and say, whatever male basketball players were experiencing in the 1970’s.

    one more thought: your take on fatigue patterned shorts? you said only jeans were a no-go, but i think this too often sported pattern should also be on the automatic veto list.

  2. CYH says:

    I’m not sure what exactly was the impetus for the recent trend of shorter men short’s. I don’t know how much the 70’s era basketball shorts have influenced this particular trend, as those were *really* short, whereas the mainstream version of the couture style is a little bit less revealing.

    I think with most things fashion, it came about by needing to be different to stand out. If everybody is doing long shorts, then to make a name for yourself you do the opposite, and you end up with short men’s shorts. Same goes for ties (though I definitely applaud this trend), cut of ones trousers, etc. It’s just to be different. I remember, not to long ago, seeing a ton of men’s capris style short/pants…perhaps this is in rebellion to that?

    You mean camo shorts? Yeah, I’m not so much for that either. If you want a little bit more pop in your shorts, go with a madras, plaid, or striped pair. Leave the camo to the professionals.

  3. […] Just like with shorts, the most common mistake is going too baggy. The key here is to go for slim and precise leg […]

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