from brogues to sneaks:

dressing up with sneakers:
almost every guy has at some point or another considered sporting a suit or slacks with sneakers. for the most part, most of us even have a few tried and failed attempts - that's good, and now here's how to nail it.
first, a foreword: own a pair of solid shoes, i'm referring to leather-bottomed brogues/wingtips/cap-toes in black or dark brown. if you don't have a rock solid dress shoe, then stop reading here, and start reading here, because understanding the suit with sneakers look is understanding how to dress a suit down. you should know how to dress a suit up before learning how to dress it down for the same reason that you need to truly learn the rules before you can artfully break them.

here's the basics:
keep your sneakers clean and simple without a chunky sole, this has been stated before. as a man grows up, so should his style. to explain good sneakers for suits, i like this quote from an article by gq explaining the style commandments:
It’s fine to own crosstrainers and running shoes and hightops. but save them for the gym. when you’re on the street, keep your sneakers simple and classic. go for ones like stan smiths, jack purcells, and sambas. they work with everything, including suits.

next, the look should generally be informal (like the picture at the very top) - sneakers look great with cotton pique suits, sock-less, with the tie a bit loosened, and maybe topped off with a messier hairdo. you're wearing sneakers with a suit, so don't take yourself too seriously, it's ok for a few things to sit a bit off-kilter. in fact, it's essential to have at least one or two other things in your ensemble to be less formal in nature.

as always, consider your proportions and fit. the worst is for your sneakers to be swallowed up in a sea of pant folds, or for your trim and cut suit to be off balanced by some massive skate shoes or dirty worn out kicks. a simple shoe without a chunky sole is critical, and i know this is hard, but a shorter very trim and tapered trouser leg like the one above looks best and shows some sock (or lack thereof) to finish off the look. sport the sneakers with your suit, just remember to keep the look casual, taper and raise the hem of your trouser, and keep your shoes simple and classic.

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