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Do I get a pair of Sperry Topsiders, and in what colour is the most 'classic'? Are there other options? Are socks not allowed?
No, n/a, yes, no, no.
I wouldn't call that stepping out of the crowd. Have you ever been to a high school?
A sport coat and knee socks.
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.
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.
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.