Opening Ceremony x Timberland Water Shoe
Buy It Now at Opening Ceremony, $48

Toeing the line between a sick tech sneaker and a casual shoe, water shoes have traditionally been well… really, really ugly. Like, “no one should wear these” ugly. Then Opening Ceremony reworked Timberland’s water shoe a couple of years ago, and they actually came out looking really dope. Mixing a simple silhouette with pops of color and using materials like waterproof suede, mesh, and neoprene, they’re like a wetsuit for your feet… and your feet will feel like Laird Hamilton, or something. Look, the point is pro surfers get laid a lot, and these will help you do that too.

Doc Martens Barrett Tassel Loafer
Buy It Now at Zappos, $126

The Tassel Loafer is the Penny Loafer’s classier cousin, and is often thought of as being a bit dressy. This interpretation by Doc Martens sticks it on a lightweight sole and adds a kiltie at the end for extra European influence.

Chambray LP Slip-On
Buy It Now at Vans, $55

The slip-on sneaker and summer go together like peanut butter and jelly. Ever since slacker Spicoli rocked the checkerboard Vans in Fast Times At Ridgemont HIgh, they’ve been associated with burnouts, stoners, and chill-ass dudes ever since. Get some menswear cred by copping them in this breathable chambray fabric.

Bass Buckingham
Buy It Now at Shoes.com, $79

Gleaning their name from the nubuck material they’re made from, bucks are a lightweight oxford made for stomping around in the summertime. Whether you rock them with a cotton suit, shorts, or light trousers, you can’t go wrong. Sure, you can opt for a white pair and mess them up with grass stains and the like over the course of the season, but a nice brown pair of “dirty” bucks will go a long way in terms of what you can rock them with.

Sperry Topsider for J. Crew Washed CVO Sneakers
Buy It Now at J. Crew, $75

Plimsolls are the fancy Euro term for any old canvas and rubber sneaker. Whether you stick with classics like Vans Authentics, Chuck Taylors, or Superga 2750s, you can’t go wrong. Dirty ’em up all summer long, and throw them in the washing machine to freshen them up when they get rank. Just don’t put them in the dryer. In fact, dry them in the sun for a cool faded look over time.

Brown Beefroll Crepe-Sole Penny Loafer
Buy It Now at Oak Street Bootmakers, $336

This preppy mainstay gets a facelift from the heads at Oak Street Bootmakers, throwing it on a lightweight crepe sole that’s perfect for summer stunting, and when they get worn down you can definitely replace them with another sole of your choosing. The “beefroll” stitch at the sides and apron stitch at the back keeps things casual, so rock these with shorts, jeans, or anything really. Who says you can’t wear them with a tank top or tee?

Quoddy Canoe Shoe
Buy It Now at Quoddy, $245

Consider these the summertime equivalent to a boot. Combining the light ruggedness of a boat shoe with the ease of wear of a slipper, camp mocs have been outfitting cool dads for centuries. Not saying they’ll make you look like an old man, but these are the perfect warm weather footwear choice to rock with your faded selvedge jeans and close-cropped facial hair. Quoddy’s been making great ones for years, and the quality Chromexcel leather will feel like butter against bare feet. Just be sure to use shoe trees to keep them looking and smelling fresh.

Sebago Docksides
Buy It Now at Sebago, $100

With their lightweight soles and handsewn construction, boat shoes are the ultimate summer shoe. Nothing feels as comfortable as a sneaker yet looks great with a crisp pair of linen trousers or lightweight chinos. Even rapper Kitty Pryde thinks you should wear them, so heed her advice and take “the classy route” this season.