Tuesdays with the Pretty Girls: Who (should) wear short shorts? We should…maybe.

Fred from Unabashedly Prep on location in Hawaii sporting the short shorts.

Ladies, how do you feel about the inseam on men’s shorts creeping closer to your own (i.e. 5″ inseam)?

F. E. Castleberry / UnabashedlyPrep.com


I LOVE short shorts on men. (And speedos.) Always have. My pick: A pair of vintage Ocean Pacific’s on tan and toned legs. Oooh, or- 7″ inseam Carhartt cords. Not sure where you can still acquire these but happy hunting, men!

Guys in itty-bitty teeny weeny shorts always make me think of uber preps on their way to their tennis games. Unless you’re running a marathon, shorts should not reveal your pasty thighs. Booty shorts may be worn only as a joke… and please cross your legs when you sit.

Just as I don’t prefer men wearing deep V-neck shirts or denim as skinny as mine, I also don’t want them wearing shorts as short as mine. I haven’t seen many men attempting to pull off the 5″ inseam so I can’t say it never works (and Steve McQueen alone proved it can). I will say, however, that if you are even thinking of attempting this look, you better have some muscles on your bones and some sun on your skin; moxie doesn’t hurt, either.
I have no problem with men wearing shorter than the norm shorts. Comfort is key. If you’re comfortable and confident with showing off those muscular legs, go for it.
Not a fan.
Alright, so long as your pack of Reds 100’s isn’t coming out the bottom of your shorts, I say I’d feel comfortable myself wear a pair of short shorts. Hell, I sleep in a pair a 6’5″ Olympic runner would deem a little on the risque side. But I dig em.
Got a question for the Pretty Girls? Send them to MomentumofFailure@Gmail.com.


9 responses to “Tuesdays with the Pretty Girls: Who (should) wear short shorts? We should…maybe.

  1. Ahh, I’m kinda ambivalent on the short shorts thing… Though I do HATE super long shorts that look like high-water pants, I’m also not a huge fan of too much guy knee. But I do think it’s ok if you’re European. Weird, I know.

    Live Love LA

  2. Usually not a fan, but on FE, anything looks great!

  3. I think a guy should wear short shorts if he wants to and I’m not going to rag on him for it. I’m sure half of the things I wear guys don’t like. But as long as guys rock them unapologetically, I don’t think it really matters. If you can pull them off and if you can project that, it just comes off as confidence. And that’s sexy. Plus, sometimes it’s damn hot and you just need to be as scantilly clad as possible. I’m not going to make a guy sweat in longer shorts while I’m all airy in super short shorts.

    • momentumoffailure

      I agree to a point: When the inside of the pockets start poking through the bottom, I think a line must be drawn. Aside from that, shorts, when worn, like you said, “un-apologetically,” at any length are fine. Well, no. No jams.

  4. Does the showing of pockets apply to women’s denim cutoffs? I don’t have any that show pockets, but I’ve seen many. But I guess that’s a question of whether guys think there is such a thing as too short of shorts/skirts/dresses on women, and that’s not the topic at hand so disregard my digression 🙂

    • momentumoffailure

      That’s a fine line too, but it’s a line women I feel can get away with WAY more than guys. There’s a white trash border of which you need to be careful, but for the most part, short shorts get me every time.

  5. I like to have my shorts hit right above the knee. With swim shorts however, I don’t mind a slightly shorter inseam.

  6. I think shorter guys actually have the advantage here and can pull off the shorter inseam because it’ll help add length to their lower half. The same rules don’t apply to women as taller women can still wear shorts mid thigh, a little higher if possible but for men of the same height, I personally feel it won’t work.

    I like my shorts to be right above the knee (and not skinny/tight but slim fitting) but the length Fred has his is also right on the money.

  7. I am less confused by guys in short shorts than I am the girl in the giant purple scarf at the top of this post. Is that scarf trying to eat her neck away? Is it some sort of boa constrictor/scarf hybrid? I think we should be less alarmed by guys in short shorts, because they are all horrible people who don’t deserve our attention, than by girl who are being attack by ugly, terrible, and make no sense scarves. It’s a public service really.

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