Can You Wear Socks With Sperrys? Should You? (Ask an Effortless Gent)

by Beau Hayhoe  |  in Style Tips

Stepping into warmer weather in style requires some careful consideration, and occasionally, brings up a question or two.

Sure, you’ve got your classic Sperry Top-Sider boat shoes at the ready, but there’s a catch: Can you wear socks with Sperrys? Heck, should you wear socks with Sperrys? 

Before you hit the boardwalk, let’s dive in. 

close up of tan boat shoes standing on a blue carpet and a reddish carpet

Can You Wear Socks with Sperrys? 

Yes, you can wear socks with Sperrys. However, there are a few crucial details to keep in mind when rocking your Sperry boat shoes this summer.

Boat shoes were originally designed, as you might have guessed, to be worn on the deck of a boat, all the better to prevent slippage while maintaining a sturdy grip on wet surfaces.

The upper was water-resistant, and the soles were also slip-resistant to aid sailors on the water.

These days, they’re both a solid summer style move – often worn in rather preppy fashion – yet still just as useful to wear on an actual boat (or on a boardwalk back on dry land). 

Sperry boat shoes are traditionally worn sockless, although again, you can wear socks if you prefer. Sperry socks men could be the key to unlocking your go-to summer shoe, after all. 

What Socks Should I Wear with Sperrys? 

If you do choose to wear socks with your Sperrys – which, again, you can certainly do! – you can nod to the shoe’s old-time heritage by wearing no-show socks. Sperry even makes no-show socks these days (more on those in a second). 

If you’re wearing Sperrys with shorts casually, going sockless or rocking no-show socks is your best bet – no calf-length socks with shorts, please. And if you happen to be on a boat, we recommend going sockless – the old-school way.

If you’re choosing to wear socks with Sperrys and dressing casually (wearing shorts, for example), no-show socks create a smooth, clean look.

Sperry brand no-shows are of course made with Sperry Top-Siders in mind. If you want the best no show socks for Sperrys, you just might be in luck with the brand itself. In fact, Sperry Top-Sider socks could prove a new favorite pair (or pairs!).

For Barron’s personal go-to, he likes Boardroom Socks’ no-shows, which work well for many different types of shoes, from sneakers to (most) loafers. Your mileage may vary, but definitely worth a shot if you want a solid no-show sock option.

If you choose to dress up your Sperrys ever-so-slightly, go with a dressier, subtle sock. These Boardroom Socks merino wool socks wick away moisture and are naturally anti-microbial. I linked to the black colorway, but they have plenty of options (don’t get black).

Pima cotton is another material that works nicely in socks of both long and short lengths. In this case, it’s lightweight and breathable – the textured knit of this pair also provides a dash of visual interest.

When Can You Wear Socks with Sperrys? 

Just as with any menswear essential, there are still some do’s and don’ts when dressing casually and wearing Sperry boat shoes. If you’re outfitted in a casual or smart casual look – and away from the water – you certainly can wear socks with Sperrys.

If you’re outfitted in long pants – say, linen trousers or classic chinos – calf-length socks are acceptable with Sperry boat shoes (in the same manner you’d wear dress socks with Oxford dress shoes, for instance). 

That being said, if you’re getting cleaned up for a formal or black tie look, shelve the Sperrys: They still aren’t a substitute for real leather dress shoes. 

What Are The Benefits of Wearing Socks with Sperrys? 

Wearing socks, even with a style of shoe traditionally meant to be worn sockless, can aid in comfort and blister prevention, especially if your shoes are brand-new and might require a touch of break-in time. 

top down close up of man wearing tan chinos and red boat shoes

No-show socks can also prove helpful if you’re stepping back into your Sperry boat shoes after being at the beach, for instance – provided your feet are dry and not covered in sand. 

This also begs the question: Can you wear socks with any pair of docksider shoes or boat shoes? The answer comes down to preference, as well as the cut of the show: Sperry Top-Siders work well with no-show socks, and most boat shoes are cut in a similar design. 

The same rules apply, too: No socks with boat shoes on the water, and socks are acceptable back on solid ground in smart-casual or casual looks. 

Is It Worth It To Wear Socks With Sperrys? 

In matters of comfort and blister prevention, it can certainly be worth it to wear socks with Sperrys, especially if you want to add a touch of flair to smart-casual looks via socks with texture or a slight pattern. 

Socks with Sperry shoes are also a wise move if you’re breaking in a new pair of shoes, or if you prefer the more stable feel of, say, a no-show sock with boat shoes. 

That being said, Sperry shoes are traditionally worn sockless, and they should prove comfortable and functional either way (particularly if you’re on the deck of a boat). 

It comes down to personal preference, but keep a few crucial rules in mind – and find the right pair of socks – and you won’t step foot off the well-worn path of the stylish, well-dressed summer fellow.

Do you have a hard stance on socks with Sperrys? Are you a purist, sockless Sperry wearer? Or are you all about the socks no matter what? Let us know by hitting us up on Instagram.