Is It Worth It To Wear Socks With Sperrys? 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. 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. 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. 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. What Are The Benefits of Wearing Socks with Sperrys? 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. 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). If you’re outfitted in a casual or smart casual look – and away from the water – you certainly can 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. In this case, it’s lightweight and breathable – the textured knit of this pair also provides a dash of visual interest. Pima cotton is another material that works nicely in socks of both long and short lengths. I linked to the black colorway, but they have plenty of options (don’t get black). These Boardroom Socks merino wool socks wick away moisture and are naturally anti-microbial. If you choose to dress up your Sperrys ever-so-slightly, go with a dressier, subtle sock. Your mileage may vary, but definitely worth a shot if you want a solid no-show sock option. In fact, Sperry Top-Sider socks could prove a new favorite pair (or pairs!).įor 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. If you want the best no show socks for Sperrys, you just might be in luck with the brand itself. Sperry brand no-shows are of course made with Sperry Top-Siders in mind. If you’re choosing to wear socks with Sperrys and dressing casually ( wearing shorts, for example), no-show socks create a smooth, clean look.
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