The promise of fall beckons: Crisp, cool air, rich foliage, the great outdoors calling your name with their many pursuits: Seasonal weddings, bonfires, days and nights enjoying the finer things in life (whiskey, anyone?). Of course, you can – and should – tackle each of those pursuits with the right wardrobe. Your rugged-meets-refined dress boots are a given, but what about socks for dress boots?

Dress boot socks are a detail not to be overlooked, one that can make all the difference between a comfortable, just-right fit and a pair of socks that slip and slide around. You’ve worked hard to build an #OOTD from the ground up, so don’t let the little things pass you by – and yes, the best socks for dress boots qualify.

Wondering where to start? Before you can lace up those boots, you need the right socks – allow us to introduce our Fair Isle Socks.


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What You Need to Know About Socks for Dress Boots

In the same way that you’ve swapped out your white leather sneakers for dress boots this season, you should swap out your socks accordingly. There’s a sock for every season, and every occasion. For instance, while the best tuxedo socks are a dashing choice for black tie affairs, most dress boots boast a sturdier outsole and insole – and need a slightly thicker sock as a result.

Enter our Fair Isle Socks, which we think pound-for-pound can certainly pass muster alongside a trusty pair of broken-in leather boots.

The Magic of Merino in Dress Boot Socks

We make these socks in North Carolina from a soft merino wool blend – when we say soft, we mean soft. A thicker sock, after all, doesn’t have to mean they’re scratchy or stuffy. Merino wool naturally regulates temperature and wicks away moisture, and it also insulates against cold – the material is utterly perfect for a pair of socks to wear with dress boots.


merino wool socks for dress boots


We’ve woven in other materials for stretch and added durability, like nylon, acrylic and spandex, but merino makes the difference (in our humble opinion).

Thick yarn and a heavy-gauge knitting process gives these socks long-lasting, sturdy appeal, and the heel and toe have been reinforced for durability. Put it this way: For as much as you wear your favorite pair of dress boots, these mens dress boot socks are up to the challenge.

What Socks Should I Wear with Dress Boots?

When it comes to prime fall style, you’ve two options (from the rest of our lineup, naturally). Our over the calf dress socks can still serve you well with slightly more lightweight fall boots, like Chelsea boots or chukka boots. Plus, the extra length ensures they stay put all day long.


olive and navy striped over the calf dress socks with chukka boots


On the other hand, a thicker pair of boots – like Red Wing Heritage’s iconic moc toe boots, or the tough-as-nails Iron Ranger Boots – call for thicker socks. The great thing is, you can dress up either pair with a tweed suit or timeless chinos – add soft merino socks in a sharp pattern, and consider yourself set.

We’d encourage you to “go beyond the boot” with any pair of Fair Isle Socks your heart desires.

These can even pull double-duty with fall-friendly high-top sneakers or even sturdy-soled brogue lace-up dress shoes. We ultimately think our Fair Isle Socks are some of the best socks for dress boots, though.

Style & Substance in Socks for Dress Boots

One thing you’ll notice right away with these new socks: The classic Fair Isle pattern, a Shetland Islands knitting technique that laces colorful yarns together in equally colorful motifs. The pattern is distinctive, handsome and rugged, and here, we’ve used four neutral, versatile colors as the base for that pattern.


man wearing navy merino wool fair isle socks sliding on dress boots


These socks are practically begging to be shown off beneath the cuffed hem of inky blue selvedge, or better still, a crisp pair of rust-hued chinos alongside your best navy shawl cardigan.

To recap: A soft merino blend delivers a warm hug and cushion for your feet, the kind that can stand up to sturdier dress boots in style, thanks to the timeless Fair Isle pattern.

Opt for black cotton socks if you’re wearing a lightweight chukka or a lightweight pair of Chelsea boots. The rest of the time, you’ve found your new go-to pair of dress boot socks – start planning your next fall adventure now, in style.


Shop Socks for Dress Boots

Editorial Staff
Editorial Staff

Our editorial staff is comprised of menswear experts dedicated to providing you with helpful information. Sharing everything from style tips to sock care instructions, these gentlemen are a wealth of knowledge for both our customers and the Boardroom Socks team.



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