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How do you style shorts?

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I don’t really know how to style shorts or what type of shorts I should get and I’m looking for advice. Im about 5’5 and most of the shirts are have go really well with jeans. I’ve tried looking for guides and what other people at my school wear but when I’m in short of a rack of shorts I have no idea what to get.
 

johng70

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Some additional thoughts on shorts:
  • Unless you're actually hiking/backpacking I would avoid cargo shorts
  • My preference is for shirts to be un-tucked with shorts - if you go this route you want shorter shirts - it looks a bit sloppy if the shirt is too long
  • footwear to match depends on how casual you want to go and what you'll actually be doing:
    • Loafers (e.g. penny loafers)
    • Tennis shoes (my least favorite option)
    • boat shoes (if you prefer the preppy look)
    • Sandals or Flip-flops for ultra-casual
  • If you're going to be in high heat and/or a lot of physical activity you want to look at shorts designed with purpose not just fashion.
    • For example, on my beach vacations I have some shorts made by Billabong (they make board shorts) - great technology that is light and can get wet and dries quickly for when I'm going to be physically active and around water.
    • For hiking / camping I have various shorts that are technical in nature
    • For the rest - I prefer chino-style shorts
  • Shirts:
    • For casual wear when it's hot, I like linen or silk button downs - they're lighter and more breathable than cotton.
    • For ultra casual I still like t-shirts.
    • As with wearing shirts with pants, make sure the shirt is properly fitted to your body shape - not too loose or too tight (unless you really have the muscle tone to pull off a tight shirt)
 

rjc149

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This advice is intended for an older person. If you're in school, you're young, and you have more latitude with how you dress.

For street wear, go with chino shorts that end 1-2 inches above the knee, and are tapered down to the opening. You don't want shorts that bell out (giving a pyramid shape) or cover the knee. You want them to be smaller, shorter, and more fitted. If you're 5'5, large baggy shorts will emphasize your modest stature.

Don't wear cargo shorts for street wear. Hiking only. And avoid jean shorts if you can -- especially if they were formerly long pants.

With footwear, you want to go with a slimmer, more understated sneaker that is intended for casual wear -- not exercise. Again, you're young so you can be a little louder with your footwear. I personally have wide feet so the canvas Sperry/Vans/Converse or leather "fashion sneaker" don't work for me. I wear a pair of suede New Balance vintage-style sneakers with shorts.

Make sure your socks don't rise above your ankles. You want to give your legs the appearance of being long and slender, which is flattering. Ankle socks or tube socks will break that continuous smooth line from your hip to your ankle, and make your legs appear shorter and stubbier.

Since I never wear sandals or flip-flops anywhere but inside my apartment or in a sketchy shower stall, I can't recommend them as street footwear with shorts. There are studies showing that your feet get covered with an absolute f--kton of disgusting bacteria and filth if wearing sandals out and about. It also limits mobility. Not sure why it's so popular. But it is.

If you're a boat shoe guy, go with no-show socks. I can't recommend going sockless, since my buddy does that and his shoes smell like decomposition and anus when he removes them. I can smell his feet when we're at the bar. But if you want to go sockless, go there. I suppose it's stylish. Same goes for loafers.

Personally, I don't ever tuck shirts into shorts -- shorts are ultra-casual summer lounge wear, and tucking a shirt is an attempt at formality that I feel is out of place with shorts at best, and pretentious at worst.

Any shirt intended to be worn untucked goes well with shorts. I like long-sleeved linen shirts with the sleeves rolled up and a tank top underneath.

I like canvas belts for shorts. It's more comfortable and breathable, and again, the belt should be covered with your shirt anyways.
 
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Panama

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I am updating my shorts with Mr Marvis pique waffle shorts, they will complement my new Rivieras. I have plenty of Smedley and Sunspel Polo's and lightweight linen and cotton shirts.


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dieworkwear

Mahatma Jawndi
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I personally like short shorts that flare out a little. Shorts that are about mid-thigh and have a 5" or 6" inseam (I'm 5'10" and normally wear a 30" inseam). I think when the leg flares out, it gives the illusion of leg muscles. Also just looks sportier to me.

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I think those sorts of things can be worn with camp collar shirts, Cuban collar shirts, looser linen shirts, etc. I wear them with Vans slip-ons or huaraches.

I also love the look of short shorts with a long-sleeved knitted top. Something like a thin sweater in the early spring months or a long-sleeved tee in the summertime. Harrison Ford wore this once to a film festival. Love the look.


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I personally struggled with shorts when I tried to stay too conservative. At that point, the look just doesn't feel comfortable to me. Almost made me feel like a schoolboy. Like these long chino shorts with a polo.


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I think when building a casualwear wardrobe, you just have to find what resonates with you. Every niche has its own look for shorts. If you're into workwear, you can wear Freenote Cloth's deck shorts with a stout white tee. If you're into sportier looks, Patagonia Baggies look great with long-sleeved tees. If you're into prep, you can wear those sorts of chino shorts with a polo.

Sounds corny, but I would go by your eye and what emotionally resonates with you. Some examples of short outfits I like:


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mak1277

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I like the fits posted, but I have a hard time with the shorts+jacket or shorts+sweatshirt in practice. If it's warm enough for shorts, rarely is it cool enough to tolerate a sweatshirt or jacket. Maybe just me, but there is probably only about a 3 degree temp range where those fits would work.
 
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dieworkwear

Mahatma Jawndi
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I like the fits posted, but I have a hard time with the shorts+jacket or shorts+sweatshirt in practice. If it's warm enough for shorts, rarely is it cool enough to tolerate a sweatshirt or jacket. Maybe just me, but there is probably only about a 3 degree temp range where those fits would work.
I find it works in temps between 65 and 75. That's much of the Bay Area during this time of year.
 

johng70

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I like the fits posted, but I have a hard time with the shorts+jacket or shorts+sweatshirt in practice. If it's warm enough for shorts, rarely is it cool enough to tolerate a sweatshirt or jacket. Maybe just me, but there is probably only about a 3 degree temp range where those fits would work.
it depends on environment. In some climates or times of year you can have a 20 degree temperature swing. So layering is important. If you ever go to a high desert climate or Midwest US in the Spring/fall this is pretty common
 

mak1277

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I find it works in temps between 65 and 75. That's much of the Bay Area during this time of year.
Makes sense, and I could probably live with it in that range, if it wasn't humid. But honestly, I'm still wearing trousers until it gets near 80.
 

rjc149

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Same, if the daytime high is over 75 F then I’ll wear shorts. 65 to 75, chinos. 65 or below, jeans or chinos. I generally keep my shorts in storage from Labor Day to Memorial Day unless there are unseasonably hot weekends.
 

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