The Most Comfortable Dress Socks for Men 2023

The most highly sought-after characteristic in dress socks: Comfort.

This installment in our Most Comfortable Series is all about the most comfortable dress socks for men.

And when we use the term comfortable, you might be wondering what level of comfort we’re actually talking about here.

To make our Most Comfortable List, we’re talking about socks that fit like a second skin. A pair that you’re happy to put on and then forget you’re even wearing levels of comfort.

Now, of course, we know that men come in all different shapes and sizes, not to mention have different preferences when it comes to fit, fabric type, etc.

For this reason, it’s difficult to promise that each pair of socks listed here is going to fit and feel perfect to you.

So, while there may be some scrolling and a little trial and error involved, we’re confident that you’ll find a pair of incredibly comfortable dress socks on this list that fit just right and become your new favorites.

Note: Featured products are independently selected and reviewed by The Underwear Review. If you purchase through our links, we may earn commission.

1. Mack Weldon Silver Extended Crew Dress Socks

Shop at Mack Weldon: Mack Weldon Silver Extended Crew Dress Socks

The Mack Weldon Silver Extended Crew Dress Socks feature a signature ionic+ silver fabric infused with super-fine Pima cotton for comfort and anti-odor properties. These socks have a cushioned footbed, stay-put pique cuffs, and an extended crew length.

2. Bombas Dress Calf Socks

Shop at Bombas: Bombas Dress Calf Sock

The Bombas Dress Calf Socks feature a lightweight fine gauge knit with a cushioned footbed, seamless toe, and honeycomb arch support system. These socks have a slightly shorter mid-calf length with stay-up technology.

3. Calvin Klein Flat Knit Dress Socks

Shop at Calvin Klein: CK Flat Knit Dress Socks

The Calvin Klein Flat Knit Dress Socks feature a soft flat knit combed cotton blend with ribbed knit trim and subtle logo styling. These socks have a modern mid-calf length and stylish seaming details.

4. Calvin Klein Ribbed Logo Dress Socks

Shop at Calvin Klein: CK Ribbed Logo Dress Socks

The Calvin Klein Ribbed Logo Dress Socks feature a combed cotton stretch blend in a wide ribbed knit design. These socks have a modern mid-calf length, subtle logo styling, and stylish seaming details.

5. London Sock Company Dash of Class Dress Socks

Shop at London Sock Company: London Sock Company Dash of Class Dress Socks

The London Sock Company Dash of Class Dress Socks feature a signature stretch-fit cotton blend that’s finely knitted and hand finished. These stylish socks sit perfectly at mid-calf and come with a 12-month Sock Sure Guarantee.

6. Falke Tiago Dress Socks

Available on Amazon: Falke Tiago Dress Socks

The Falke Tiago Dress Socks feature a premium cotton fabric with slight sheen, color brilliance, and a non-slip sole. These socks have reinforced stress zones for durability and hand-linked flat toe seams for extra comfort.

7. Falke Airport Dress Socks

Available on Amazon: Falke Airport Dress Socks

The Falke Airport Dress Socks combine a fine merino wool for thermal regulation with soft cotton for all day comfort. These socks have extended cuffs to stay up, reinforced stress zones for durability, and a wrinkle-free fit.

8. Easton Marlowe Dress Socks

Available on Amazon: Easton Marlowe Dress Socks

The Easton Marlowe Dress Socks feature fine combed cotton for a soft feel on your skin that’s more durable than regular cotton. These socks add high quality nylon for comfortable stretch and are available in both solid colors and subtle patterns.

9. Tommy Hilfiger Dress Socks

Available on Amazon: Tommy Hilfiger Dress Socks

The Tommy Hilfiger Dress Socks have a soft and breathable construction with plenty of stretch for all-day comfort. These socks have a lightweight yarn and are available in multiple colors and prints.

10. Polo Ralph Lauren Ribbed Dress Socks

Available on Amazon: Polo Ralph Lauren Ribbed Dress Socks

The Polo Ralph Lauren Ribbed Dress Socks feature a stylish rib-knit design in an extra soft and comfortable cotton blend. These socks have ribbed cuffs, a signature embroidered pony, and are available in multiple colors.

If you’re all about comfort when it comes to your socks, shirts, and underwear be sure to check out the rest of our Most Comfortable Series.