The rules of wearing boat shoes

The best thing about getting dressed this time of year is not having to think too hard about what you're putting on. But, if you want to look good, you can't throw away the rules completely. Take summer's iconic boat shoe, for example. Too little consideration for how you're wearing them and you might look like a guy who just got kicked off his college campus. (If you're over 30, that's an especially unfortunate look.) But observe a few simple rules and you can basically go on auto-pilot for the rest of the summer. That said, here's what those rules are. As for the rest of your summer gear, check out our What to Wear Today series for all kinds of easy-to-follow, important-to-know advice.

Stick with the Classics

Unlike driving shoes, which come in a range of bright colors, we tend to think boat shoes look best when they're simply luxurious versions of the original Sperry Top-Sider from 1935. Think: Neutral leather, moccasin-style upper with rugged laces and a slip-proof rubber sole. Wen it ain't broke, don't fix it.

Sperry Top-Sider burnished-leather boat shoes, $85, available at mrporter.com

Get Some No-Show Socks

Unless you're experimenting with some new-wave take on '80s, Ivy League prep (which admittedly, could be cool) it's best to keep your ankles bare. But don't skip socks completely or your boat shoes won't make more than a few weeks. Grab some no-show socks made for shoes with a lower vamp.

Nice Laundry Ghost no-show socks, $49 (pack of 6), available at nicelaundry.com

Go for Shorter Length Pants

You see a lot of guys wearing boat shoes with pants so aggressively rolled, they look like they just came off the shore. Remember: A little roll goes a long way—especially when you're nowhere near the dock. When in doubt try cotton trousers, suits, and jeans that skim the tops of your shoes to begin with.

Vince cropped chinos, $198, available at matchesfashion.com

Keep the Preppy in Check

The boat shoe is a preppy staple, so it'll feel at home with chinos and polo shirts. Perfectly fine. The objective is to look like JFK and not your average American frat guy, so pump the breaks on pastel colors, embroidered belts, and Croakies. It never hurts to keep it simple.

Orlebar Brown Albert polo shirt, $310, available at orlebarbrown.com

This story originally appeared on GQ.