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What do I wear with shorts and a polo?

post #1 of 59
Thread Starter 
Do I get a pair of Sperry Topsiders, and in what colour is the most 'classic'? Are there other options? Are socks not allowed? Also do I iron creases into chino shorts?
post #2 of 59
Almost 1,000 posts and you're asking this? C'mon man, this is pretty basic; boat shoes, plimsolls, espadrilles, drivers, etc... in whatever color you want.
post #3 of 59
Quote:
Originally Posted by BareSolid View Post
Do I get a pair of Sperry Topsiders, and in what colour is the most 'classic'? Are there other options? Are socks not allowed?
Also do I iron creases into chino shorts?

No, n/a, yes, no, no.

Do not under any circumstances get the most boring option of every white middle aged, middle income American in the summer time. No boat shoes, no baggy chino shorts, no bandy legs with skinny bare ankles.

Get some adidas Stan Smiths and wear with short white socks. Make sure your shorts are tapered to fit the width of tour legs. Do not go bare ankled. There are loads of adidas Samba or Gazelle colourways if you want to match them up or show a bit of colour. Show some imagination and step out of the crowd.
post #4 of 59
A sport coat and knee socks.
post #5 of 59
Quote:
Originally Posted by Ianiceman View Post
No, n/a, yes, no, no.

Do not under any circumstances get the most boring option of every white middle aged, middle income American in the summer time. No boat shoes, no baggy chino shorts, no bandy legs with skinny bare ankles.

Get some adidas Stan Smiths and wear with short white socks. Make sure your shorts are tapered to fit the width of tour legs. Do not go bare ankled. There are loads of adidas Samba or Gazelle colourways if you want to match them up or show a bit of colour. Show some imagination and step out of the crowd.

I wouldn't call that stepping out of the crowd. Have you ever been to a high school?
post #6 of 59
Quote:
Originally Posted by chrisb0109 View Post
I wouldn't call that stepping out of the crowd. Have you ever been to a high school?

It's certainly stepping out of the crowd of boring gits I see at every diner I've ever been to on a Sunday. Sambas would be an earth shatteringly radical departure for these dullards.
post #7 of 59
boat shoes / sockless loafers.
post #8 of 59
Quote:
Originally Posted by Mr. Moo View Post
A sport coat and knee socks.

This.

Don't forget the balmorals
post #9 of 59
Quote:
Originally Posted by Ianiceman View Post
It's certainly stepping out of the crowd of boring gits I see at every diner I've ever been to on a Sunday. Sambas would be an earth shatteringly radical departure for these dullards.

It'll just make you look like your average high schooler instead of your average adult.

Neither is necessarily desirable.
post #10 of 59
This is a classic, but unconventional enough to get you up out of the Topsiders/Weejuns rut.

http://www.llbean.com/llb/shop/11575?feat=pprv
post #11 of 59
looks like a boat shoe designed by a more rustic company.
post #12 of 59
A pair of very well worn saddle shoes, loafers, or oxfords can make a noticeable addition to (and this is key here) a well-fitted polo and short.
post #13 of 59
Quote:
Originally Posted by Irving View Post
A pair of very well worn saddle shoes, loafers, or oxfords can make a noticeable addition to (and this is key here) a well-fitted polo and short.
+1. A classic look regardless of the age of the wearer.
post #14 of 59
If you go with boat shoes, I strongly advise navy ones, with either a white or red sole
post #15 of 59
Quote:
Originally Posted by Ianiceman View Post
No, n/a, yes, no, no. Get some adidas Stan Smiths and wear with short white socks. Make sure your shorts are tapered to fit the width of tour legs. Do not go bare ankled. There are loads of adidas Samba or Gazelle colourways if you want to match them up or show a bit of colour. Show some imagination and step out of the crowd.
I might steal this tip. I rarely wear polos with shorts (preferring guayberas and other button downs), but for when I do I usually go with running shoes or flips flops. I like the Stan Smiths.
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