The world of business casual has changed. Where boat shoes were once as gauche as white crew socks with your double-breasted, now they’re quite workable. As the world has come to recognize that the nattiest dressers aren’t always the best business minds, and that sometimes genius comes in a mock turtleneck or even a robe and slippers, the rules of how to dress for a business meeting have been overhauled. Along with notions like the fluid workspace, studies are now showing that being comfortable is as important to being productive as looking like a million bucks.
The problem here is that you can’t just throw on any pair of ratty old sailor slip-ons and hope that corporate merger is going to go off without a hitch. Rather, you need to get the right boat shoes for the job, wear them the right way, and keep them in their place.
To begin with, here’s some rules for wearing business casual boat shoes, followed by our top picks.
Pick Your Venue
If you’re meeting for drinks, talking trades at the cabana, or heading to the country club, a pair of boat shoes should fit in perfectly fine. Naturally, anything that takes place near a dock or marina is a go. Our basic rule is that the more concrete there is surrounding a place, the less you should be putting on your maritime best.
Heighten Your Waters
You do not want to be wearing your pants rolled up like Robinson Crusoe, since that’s too deep on the casual spectrum. Instead, pick a pair of pants that doesn’t have a large break and just brushes the top of your shoes. It adds intentionality to the look.
Drop Your Socks
Get a quality pair of no-show socks. You can’t go completely sockless without ruining your shoes, nor can you get away with much of anything that climbs up your ankle. Keep patterns and colors dark and simple so that if your socks do flash, they still send the right message.
Keep It Classy
A set of boat shoes should look like they are in excellent repair, and if they’re able to be shined, do so. Don’t get adventurous with colors or styles. Pick a basic penny loafer form in a dark shade, preferably brown or navy.
Complete The Package
Your pants should be belted with a fetching and professional piece, not some woven throwback to your studio apartment days. Colors should be muted like a Rockefeller on vacation, not a Sigma Alpha Epsilon brother in a pastel alligator shirt. Don’t be afraid to throw a light sport jacket on, just to show you’re not a beast.
Without further ado, here’s where to begin your quest for business casual style:
Tommy Hilfiger Bowman
Imported leather in multiple sedate colors ranging from forest green to a baby powder blue allow you to mix and match these to go with whatever look you’re trying to accomplish. Purchase: $42+
Dockers Castaway Boat Shoe
What really gives these a professional edge is the lack of a standard white sole. Though they don’t offer much variety as to the colors, it’s easy to mix these with a pair of summer business pants for lightweight living. Purchase: $46+
John Varvatos Schooner Boat Shoe
Breathability is the watchword here. The Schooner boat shoe is perforated all the way around to let the air wash over your tootsies. Some models don’t have that professional edge, so be careful how you choose, but if you tend to suffer from sweaty foot syndrome (SFS) these will be your new best friend. Purchase: $50+
Sebago Spinnaker Ronnie Fieg Boat Shoe
Ordinarily we’d advise you to avoid too many colors, as they tend to start looking a little more like Bozo’s evening wear than shoes for doing the work of specialists. Contrarily, the Ronnie Fieg shoes have a sense of fun that doesn’t detract from their overall stylish and earnest appearance. Purchase: $50+
Timberland Classic Two-Eye
Poron foam pumps up the comfort level, while the door-kicking toughness is hidden under a supple look. Run, jump, climb, and then sit down for some yellow tail and close that sale. Toughly practical yet pristine, there’s a reason these are a classic. Purchase: $50+
Sperry Top-Sider Men’s AO Two-Eye Python Boat Shoes
Nothing shows you’re a predator more than wearing a predator. Though made of basic leather, the python embossing has a savoir faire that is as fun and dangerous as an alligator grin. Purchase: $70
The hardest part about choosing a set of docksiders is getting just one color combo. Faded denim sits alongside black-on-black, making these almost as good in a formal setting as they are at your tailgate party. Purchase: $80
Sperry Bahama 2 Eye Black Monogram Boat Shoes
Tread carefully here, as the Black Monogram is a beautiful, professional-looking shoe, but Sperry has a few Bahama models that look more like street sneakers from your pre-teen years at the skate park. All are great for walking around, only the Monos will do you proud in a luncheon. Purchase: $95
Frye Sully Boat Shoes
Used right, the beautiful burgundy color pops and sizzles, saying you know what you’re doing but don’t need to take yourself too seriously. Used wrong, they say you can’t even dress yourself. Coordinate wisely and go bold. Purchase: $101
Allen Edmonds Eastport Boat Shoes
Extended triple eyelets provide a heavier sense of style than the dual eyelet options, covering higher on the foot for both wetness protection and hiding beneath a pant leg should your dinner turn out to be more business than casual. Purchase: $175
Rancourt & Co. Waxed Canvas Boat Shoes
Made in Maine, where waxed canvas is a way of life, these are hand-stitched and molded to provide comfort, support, and quality right where it counts. They won’t work everywhere, but those who know royalty will recognize your discerning eye in a moment. Purchase: $246
Gokey World’s Most Durable Boat Shoes
Oil-tanned, water repellant, and intended to literally be buried with you for boating across the river Styx, Hokey has forgotten more about bombproof beauty than most will ever even attempt. Purchase: $250
Paul Smith Jeans Branca Scotch Boat Shoes
From the top down, it’s easy to mistake these for a set of Paul Smith’s designer loafers. Only the rawhide ties and broad white sole give them away as anything else. The streamlined top with the pleasure cruiser bottom is a mix of work and play that doesn’t miss. Purchase: $260
Yarmouth USA Camp Moc Slip On
A single eyed loafer that’s made in Maine, each one is sewn by hand out of 100% Horween shoe leathers, leaving naught to chance. Each color palette is a who’s who of modern style, meant to catch the eye, yet still fit in with any crowd. Purchase: $310
Quoddy Moc II Leather Boat Shoes
Those who aren’t yet familiar with Quoddy would do well to learn at speed. Vibram rubber soles create a cushion of gripping comfort that will last season after season and mixes with striking seams to the Chromexcel leather that’s proudly made in the US. Purchase: $390
Salvatore Ferragamo Classic Boat Shoes
Going in a fashion forward direction, the slipper-like Ferragamos are hard not to notice. Using a squared front and silver buckle accents, you’re going to want to deck out your accessories before donning these dapper duds. Our suggestion: Embrace your inner dandy. Purchase: $422