A key fashion rule most men don't seem to know: wear running shoes when you're running, but sneakers when you're strolling. Can't count how many times I see men wear Nikes or ASCISs with jean, khakis, even a summer blazer - for the love of God, stop and buy some sneakers, man!
When it comes to sneakers, no one will begrudge you for going with a classic, like Converse, Keds, or Vans - but no one will walk up to you and say "Cool shoes!" either.
To step it up a notch, swap the canvas out for suede leather and switch the regular cap-toe of the Converse All-Star for some dressy brogue detailing. None of this has to cost any extra: to wit, the ASOS suede sneakers pictured above. The Tan Brogue Trainers cost $43 and (if you want to channel your inner Elvis) Navy Brogue Trainers cost $40. They run true to size and feel good, even when sockless. Note the shoe sizes are UK. If you - like me - treat your sneakers as beater shoes to wear the hell out of and toss after a year, you shouldn't pay more than ~$50 per pair.
Don't bother with the competition, BTW: the Hush Puppies Carver and Hawkings McGill Sheriff have cheap, awful looking suede. The Ben Sherman Nloy looks great, but fits tight and has a thin sole and cushioning. The Polo Orrick just looks weirdly off-balance with only 2 eyelets. Only the Generic Surplus Wingtip comes close, with nice suede and a comfortable lining and sole, but the wingtip is so truncated at the front that makes your foot look funny.
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