Boat shoes are slip-ons with 360 lacing and rubber soles. They’re casual and often associated with yacht club leisure. Loafers, a usually leather laceless slip-on, come in a range of styles but are overall highly dress code versatile. Driving shoes are moccasins with rubber grommet soles.
You know what boat shoes, loafers, and driving shoes are like in relation to each other? Tom Hanks’ three sons, Chet, Colin, and Truman Hanks.
Three compositions that share the same DNA, have similar templates, but more importantly, have completely different personalities.
All three shoe styles were built for different reasons.
And even if those reasons aren’t as important as how to style them (for most of us), understanding their history and purposes will bring clarity to each shoe’s strengths.
Table of Contents
Boat Shoes Explained
Origin and Design
Boat shoes are leather or canvas shoes with rubber outsoles originally made to be worn on, you guessed it, boats. Though they’re low-profile enough to slip in and out of, they feature a 360-degree lacing system that’s threaded around the collar and eyelet stays.
Invented in the ‘30s, and designed to withstand weather and elements, they boast a durable construction and water-resistant uppers. The rubber outsoles are meant to grip boat decks safely, even when they’re wet.
Other names for boat shoes include top-siders, sailor shoes, and deck shoes. By the 1970s, men started to wear them as casual shoes on wet and dry land. They have a youthful and sometimes preppy vibe.
Ideal Occasions to Wear
Boat shoes are, first and foremost, casual. However, these days, they come in a range of styles, some less casual than others. Still, I’d say the dressiest way to wear a boat shoe is within a sort of resort chic context—think linen jacket with a light cotton button-down.
Relatedly, since they have a preppy look about them, people often use them to achieve that effortless old money aesthetic. After all, they convey that you may have just gotten off a boat. If you love nautical style in general (anchor motifs and dive watches, for example), boat shoes are an effective option.
You can wear them with any casual outfit, whether a T-shirt and jeans or a polo and chinos. They’re a perfect summer shoe, ideally worn sockless.
Features and Characteristics
As mentioned, boat shoes are traditionally built to be durable. Moreover, they’re treated for water resistance, making them perfect to wear on a boat, at the beach, during a fishing trip, or any time you’re near a body of water (provided they’re true boat shoes and not a fashion-centric approximation).
The 360-lacing is one of the boat shoe’s signature visuals. They can be made out of nubuck and suede, as well as leather and canvas.
The soft, flexible rubber outsole is made for grip and traction in wet conditions but also makes them wildly comfortable shoes. I love my boat shoes so much that I sometimes wear them with thick socks during the cold season.
Oliver Cabell serves up classic deck shoes, perfect for the country club, the yacht, or brunch. Despite their casualness, they’re well-constructed and built with full-grain Italian leather
Loafers Explained
Style and Versatility
Loafers are a slip-on shoe, usually leather or suede, but not always, that are laceless and often pretty low-profile. They traditionally come with a leather outsole with a low heel. Since they’re so easy to slip in and out of, they’ve always been known for their ease, convenience, and versatility.
In the modern age of fashion casualization, they’re even more versatile. Loafers share some similarities with Oxfords. You can wear a pair of good leather loafers the same way you would a pair of Oxfords.
Though they date back to the 1930s, Loafers were once reserved for casual dress. The thing is, casual dress in, say, the ‘50s is what we call smart or smart casual today. The lines were straighter, the waists higher, and the collars common.
There were no oversized tees paired with cinched joggers back then.
However, you can still wear loafers with super relaxed combinations today too. After all, even as far back as the ‘60s, Elvis wore loafers with tube socks and casual pants.
Formal vs. Casual Wear
History aside, loafers are easy to wear in a range of dress codes partly because there are so many types of loafers. I outline the seven most common styles here, but here’s a quick rule of thumb.
The more details there are on the loafer, the more casual it is. The cleaner and simpler it is, the more formal it is. On top of that, thinner and pointier silhouettes are more formal than square-toe loafers.
So, a thin, pointy loafer in black leather? Wear it with a suit or tuxedo. A suede kiltie loafer with a lot of fringed details? Jeans—or even shorts.
Sometimes, the design will fall somewhere in the middle, so you’ll simply use your better judgment. Remember, it’s all about balance. Perhaps you’re looking at a tassel loafer. Well, a tassel is added detail, but that doesn’t necessarily mean it’s a casual shoe. What if it’s a wholecut tassel loafer with a tapered silhouette? Definitely more formal.
Meanwhile, a moderately tapered penny loafer can be worn with anything, from a full suit, to a broken suit with jeans, to even shorts. And yes, you can wear loafers with socks. Here’s how.
Materials and Construction
Today, loafers can be made out of anything. The traditional construction, as mentioned, is leather or suede with leather outsoles. If you’re in a professional or formal situation, you’ll want to stick to these.
There are also canvas loafers (strictly casual) and models with woven uppers like baskets that combine elegance with earthiness. There are even loafers with rubber outsoles, making them a bit like laceless boat shoes.
All that to say, loafers truly are one of the most adaptable shoe styles for men.
The Carmina Penny Loafer is a true classic, featuring traditional saddle and beefrolls. This smart casual design is elevated by the fact it’s handmade in Mallorca using supple calfskin or buttery suede, with a range of exquisite colorways available.
Driving Shoes Explained
Driving-Specific Features
Driving shoes were designed by Gianni Mostile in 1963. They’re a moccasin made of leather or suede, with a rubber sole equipped with grommets.
By combining a moccasin’s easy wear and comfort factor with this special new outsole, motorists were provided extra grip on the pedal. They also feature extra cushioning around the heel, offering more security and comfort.
Of course, Mostile had Italian roadsters in mind. That being the case, the driving shoe does have an old world La Dolce Vita aesthetic about it.
Today, they’re still relaxed yet sporty, but are worn in an aspirational way by all types of folks, regardless of whether or not they own a Ferrari.
Casual Elegance
The driving shoe really is like a sporty moccasin. They’re a strictly casual shoe, though like the boat shoe, you can wear them with certain suit separates for that leisurely elegant look.
Still, you’re better off wearing them with shorts, cuffed jeans or chinos, linen while on holiday, and treating it like a go-to errand shoe. They’re classier than sneakers, but still can’t be worn as formally as leather dress loafers.
While the boat shoe is more youthful and country club adjacent, the driving shoe has more of a cosmopolitan, Bond-esque vibe about it.
Even if you wore a T-shirt and jeans, boat shoes would have the same effect as a nice pair of leather sneakers. Driving shoes, however, would give it a class factor. And they’re definitely best worn without socks.
Materials and Comfort
Driving shoes are usually made from leather or suede. I prefer them in suede because it leans harder into the moccasin look, as well as relaxed sophistication.
Because of the rubber outsole, driving shoes typically don’t need breaking in. This design combines protection, stability, and cushion, especially because of the extra padding by the heel. Shoes that are too flat can be uncomfortable to walk around in, but true driving shoes don’t have that problem.
The grommets, which are rubber nubs on the outsole, increase the grip and traction. Sometimes, rubber grommets are even just attached directly to the suede or leather bottom, making it even more moccasin-like.
Sometimes they have laces, making them look like a “driving boat shoe,” and sometimes they don’t. They can also come with hardware. A horse bit driving shoe definitely has that chic world traveler look down pat.
The OC Driver makes the trip to the post office just that little bit more enjoyable. With a 3oz suede leather upper from Marche, Italy, and hand stitched and lasted in Portugal, this ticks all the Euro-luxe boxes you want in a quality driving shoe.
Conclusion
Looking for a super casual or youthful look? Go for some boat shoes. Feel free to incorporate them into a decidedly preppy outfit.
Meanwhile, a driving shoe is equally as casual but in a sporty and cosmopolitan way. They look beautiful with linen pants and undeniably cool with jeans.
As far as the loafer goes, well, is there anything more versatile? From suits to jeans, there’s a reason they’re a menswear essential.
FAQs
Are boat shoes suitable for formal occasions?
Absolutely not. You can get away with wearing them with suit separates in a man-of-leisure kind of way, but don’t wear them to any formal events.
What materials are commonly used in crafting loafers?
Loafers are commonly made with leather or suede and feature a leather, low-heeled outsole.
Are loafers and driving shoes interchangeable?
Driving shoes are too casual to be perfectly interchangeable with dress loafers. You can get away with wearing loafers in casual situations, but you can’t wear driving shoes on formal occasions.
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