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.
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.
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).
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.
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.
*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..