I never thought it came to this, but last year was my first time wearing shorts in public since 1997. I want to get back into wearing shorts, but lack the same confidence in coordinating items as I do with the rest of my clothing. Do you have any recommendations on what ensembles would look good? Currently, I have mostly comic book logo t-shirts, and my casual shoes are Converse, Doc Martens, and recently Sperry Top-Siders.
What to Wear with Shorts?
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I usually wear polos or short sleeve button down shirts with khaki shorts and boat shoes like you mention; sometimes I wear nonathletic sneakers with them.
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VR6ofpain
Good choice. They look great with shorts. Just make sure you skip the socks. If you wear socks with them, you may just get arrested.
My typical outfit:
Your ring of course. 
Actually, I go with a short sleeve button down and Birks, I live at the beach.
Actually, I go with a short sleeve button down and Birks, I live at the beach.
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If you mean Chuck Taylor Converse All-Stars, please don't wear high tops with shorts (unless they're athletic shorts and only if your going to play some hoops). Oxfords only. Thank you.
T-shirts and sandals are great with shorts. Of course, I'm in southern California. You can also go with knit polos, buttoned short-sleeve shirts and boat shoes if you want. But no socks.
First I would recommend that you wear underwear with your shorts. Don't want anything hanging out. After that do what ever you want.
Socks and sandals is a Pacific Northwest phenomenon.
Let's hope it never spreads.
Let's hope it never spreads.
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- #10
Unlike my "urban" neighbor residents, I am very much against sagging. I find it to be a very nasty, tasteless trend that has grown out of proportion.
Thanks for your advice. Xillion, a funny story: I was outside wearing the Black Lantern t-shirt, and a man passing by smiles and points toward me. Of course, I am weirded out. After pointing, he gives a thumbs up, revealing he was wearing a Green Lantern ring.
What to Wear with Shorts?
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Grownup should probably not be wearing comicbook t-shirts either.
OK, maybe one or two ironically, but they should be the exception in your wardrobe.
OK, maybe one or two ironically, but they should be the exception in your wardrobe.
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- #13
I've seriously considered it (especially since people do not recognize the difference between Superboy's logo and Superman's nowadays,) but it's among the things I can actually get away with. Hopefully, I can coordinate a guayabera with a pair of shorts.
Solid colored shorts or cargo shorts (9-inch inseam), button down shirt with tails (NOT tucked in), Johnston & Murphy basket-weave loafers in brown. A nice, casual summer look that's relaxed and classy. 
Alternate look: add white crew-neck t-shirt and leave shirt unbuttoned.
Alternate look: add white crew-neck t-shirt and leave shirt unbuttoned.
A pretty woman in a thin, short summer dress on your arm. No one will care what else you were wearing with the shorts, but they will remember the pretty woman and that she was with you. 
I wear shorts from American Eagle, 11 inch inseam I think. They fit great for a big guy like myself (6'5'' 265). I agree with the shorts, topsiders and polo look. I'm 24 and I wear that all the time to go out for a few beers with the fellas. However, if you wanted to go for a younger more athletic look, I'll throw on a pair of no-show socks and a good looking pair of sneakers (right now Im wearing all black adidas bounce cross trainers) and something of a more athletic top like a nice t-shirt. Some of my favorite t's are the super cheap, super comfortable v-neck plain t's from Old Navy.
And please, don't wear socks and sandals. As a matter of fact, don't wear sandals at all hahaha. Mandals are a crime
And please, don't wear socks and sandals. As a matter of fact, don't wear sandals at all hahaha. Mandals are a crime
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- #18
Trust me, after years of working retail, I do not have pretty feet. Sandals are the last thing on my mind. I usually like to wear Chucks during the summer time in spite of their lack of support.
Yesterday, I had on a red t-shirt with khaki cargo shorts, and these:
Yesterday, I had on a red t-shirt with khaki cargo shorts, and these:
C'mon guys...your aloha shirt, no one??!
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- #20
No aloha shirt for me. Guayabera, yes, but my aloha shirt phase was back in 2004 (btw, I need to pick up a few more.)
