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Footwear to wear with shorts

swiego

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Awkward post here but, well, here goes!

I've been a suit-and-tie workaholic for a long time, typically in climates where it doesn't get too hot, so I've never worn shorts much. Work dress code is always slacks, shirt, tie, jacket, as are many evening extracurriculars, and when it's casual times with friends it's still late enough and probably cold enough that khakis, jeans etc. are the informal clothing du jour. Now I'm traveling for work to warmer places, spending my weekends with my girlfriend who lives in the hotter parts of Texas, and basically changing my wardrobe around a bit.

I'm good with shorts and a t-shirt, but to be honest I'm at a total loss on footwear. For someone who wears dress shoes to work, cross-trainers to the gym, driving moccs at the track (fair amount of competitive racing as a long-time hobby) all with socks, but does not own a single pair of sandals or other summery footwear... what should I be looking for? Basically, at a high level, what are the broad categories of footwear that are worn with shorts (they all look like sandals to me) and what/how many would I need to build a basic starter wardrobe of summertime footwear for various occasions? (occasions = hours of walking in hot weather; beach time; boat time; outdoors kicking-back time.) Also, the cheap flipflops I used to wear when I was 7 years old at the pool are bad now, right? Just checking.

Apologies for such a basic question... I think I could identify the brand and describe the market positioning of a dress shoe by sight, but I have no idea what to wear with shorts. Help!
 

acidboy

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boat shoes and canvas sneakers.
 

j

(stands for Jerk)
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White Purcells with super short or no socks. They're surprisingly comfortable and supportive.
 

daveboxster

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Originally Posted by swiego
Awkward post here but, well, here goes!

I've been a suit-and-tie workaholic for a long time, typically in climates where it doesn't get too hot, so I've never worn shorts much. Work dress code is always slacks, shirt, tie, jacket, as are many evening extracurriculars, and when it's casual times with friends it's still late enough and probably cold enough that khakis, jeans etc. are the informal clothing du jour. Now I'm traveling for work to warmer places, spending my weekends with my girlfriend who lives in the hotter parts of Texas, and basically changing my wardrobe around a bit.

I'm good with shorts and a t-shirt, but to be honest I'm at a total loss on footwear. For someone who wears dress shoes to work, cross-trainers to the gym, driving moccs at the track (fair amount of competitive racing as a long-time hobby) all with socks, but does not own a single pair of sandals or other summery footwear... what should I be looking for? Basically, at a high level, what are the broad categories of footwear that are worn with shorts (they all look like sandals to me) and what/how many would I need to build a basic starter wardrobe of summertime footwear for various occasions? (occasions = hours of walking in hot weather; beach time; boat time; outdoors kicking-back time.) Also, the cheap flipflops I used to wear when I was 7 years old at the pool are bad now, right? Just checking.

Apologies for such a basic question... I think I could identify the brand and describe the market positioning of a dress shoe by sight, but I have no idea what to wear with shorts. Help!


If you live in Austin, then you'll find a lot of sandals. I wasn't a sandals-guy until I moved here and have a great pair of dress ones that I love to wear with shorts when wanting to dress less casually. I'm not a fan of birkenstocks, or the like. That's just a personal choice.

And, this one will get a lot of comments (guys, don't bother... enough has been written about this)... but Crocs are worn a lot by men in Austin. Frankly, I resisted them completely until my wife bought me a pair. Now I wear them frequently (gasp!) with shorts. But, NEVER with socks. And not with long pants either.
 

highball

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Leather sandals and sperry's are all good recommendations. I have a pair of suede moc-toe loafers I like to wear without socks. Why not wear your driving moc's?

I also have a pair of Onitsuka Tiger's that have a real classic tennis shoe look, but I find these harder to pull off wthout jeans than the white sneakers mentioned above.
 

borderline

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Birkenstocks are much better than flip flops. I used to wear Chacos but not so much any more.

Birks or low top Converse.
 

Flambeur

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Originally Posted by Epaulet
I also like basic white sneakers like the Adidas Stan Smith or Converse Jack Purcell.

yup, or nice well made sandals/flip-flops (preferably well-made leather ones, but not the ones that have a closing strap, etc)
 

citoyen

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oxfords. nice look. no socks of course.
 

HHD

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Boat shoes, no socks (obviously ;-)). What are your driving mocs like? You could wear those, too. I wouldn't go for sandals.
 

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