What Socks to Wear with Dress Shoes, Loafers, Sneakers, & More

When it comes to style, I firmly believe it can be a form of self-expression, an art form if you will. Certain occasions or settings lend to more confined freedoms of self-expression, like weddings and that dream job interview you’ve landed. While I’ll leave the garment style decisions to your expression, I can lend a helping hand in navigating the sock choices that will help you feel comfortable, confident, and stylish.

Now you may be asking, what credentials does this guy have in telling me how to wear men's dress socks… Well, the fact that I’ve been called a ‘gentleman and a scholar’ by someone’s grandmother while ushering my high school play, and my experience testing the best socks in the world, might be just enough wisdom to guide you in the right direction when deciding what kind of socks to wear with dress shoes.

Natural Sock Selection

Before we get into the pairing of socks and shoes, like the intricacies of wine and cheese, let’s take a moment to talk about the basics.

What makes up a good sock you ask? Well, this is where the magic of Merino Wool comes in. A natural fiber, Merino Wool is comfortable, breathable, and moisture-wicking, keeping your feet dry, thermoregulated, and comfortable all day and night. It ensures your grandma-in-law isn’t out dancing you at the reception. Or your feet don’t smell like fromunda cheese in an interview.

No matter what shoes you’re wearing, you’ll thrive in socks that are comfortable, breathable, and moisture wicking — because, let’s face it, when you feel good, you look even better.

Now that we’ve covered dress socks basics, let’s dip our toes into specific sock-shoe pairings, starting with traditional dress shoes.

What Socks to Wear with Dress Shoes: Oxfords, Derbies, & Brogues

Oxfords, derbies, and brogues are classic shoes for business or special occasions. Whether you're donning these shoes for a wedding, an important presentation, or a meeting with your future in-laws, you’ll need socks that support the look.

Best Sock Options

In formal settings with oxford shoes, dress socks that rise to a crew or mid-calf height tend to be the best suited choice. These socks should feel sleek (look for a Lightweight sock to fit inside these close-fitted shoes), and if you're looking for a sock with a little extra cushion for underfoot support, check out our dress socks with cushion.The key is balance: sleek, yet comfortable. And that parts up to you.

Keep it simple with our Solid Crew lightweight sock, or show off some personality with a lightweight Animal Haus sock. For formal occasions, The Standard Mid-Calf sock and black-tie dress codes go together like Werther’s candy and Boomers.

For those elevated casual looks — maybe pairing Oxfords with dark jeans or chinos — subtle patterns can add some fun without taking away from your overall look. A little stripe or dot never hurt anyone. That’s why we knit the Oxford Crew sock.

What Socks to Wear with Dress Boots

Dress boots are a fantastic option when the weather’s cooler or when you want to elevate a casual look. Whether you’re attending a winter wedding or just want to make a style statement, these boots need the right sock to match their refined charm.

Best Sock Options

During the winter months you may want a thicker, more substantial sock — something that can keep your feet warm without sacrificing style. Merino Wool is again the hero here.

While hiking a mountain in fancy dress boots should be reconsidered, wearing our Hike socks with dress boots could be the right option for you in the colder months. Depending on the boot height, our 1466 Hiker Micro Crew socks are a personal favorite when pairing with Blundstone boots specifically. They’re arguably the most versatile socks we knit.

If you prefer a slightly taller sock, our Hiker Boot sock will give you the same midweight thickness at a boot height sock. If you’re more after a traditional dress sock to pair with your dress boots, The Standard Crew with Cushion sock is the knit for you.

What Socks to Wear with Loafers

Loafers hit that perfect sweet spot between business and casual. Whether you're heading to the office or going out for a lunch date, loafers can be dressed up or down, depending on the occasion. This means you’d have a hard time finding a wrong sock for this shoe, that is, as long as it’s Merino Wool.

Best Sock Options

Due to the range of flexibility in style options for loafer shoes, I recommend deciding your sock choice based on season.

Summer escape to a tropical destination? Our Solid no show socks will give you the sockless look with the comfort of a moisture-wicking sock. Wearing socks in shoes not only helps the longevity of your shoes, but also the health of your feet.

In colder months, options like the Spey Fly with cushion sock will keep your ankles from being exposed to the elements.

What Socks to Wear with Casual or Semi-Dress Shoes 

For classy casual occasions, you can experiment with non-traditional footwear in a stylish way. Whether it’s dress sneakers with chinos or boat shoes with dress shorts, the right sock choice adds comfort, personality, and polish.

Boat Shoes & Sperrys

Boat shoes and Sperrys are casual footwear staples, especially when it’s warm outside. Whether you’re at the beach or writing sea shanties at the local docks, these shoes have made a comeback in recent years.

Boat shoes are best paired with no show dress socks. These socks will keep your feet comfortable without taking away from the nautical charm of your shoes.

Dress Sneakers

Dress sneakers are the perfect blend of casual and smart. They work best in business-casual environments or for an elevated casual look when you want to be comfortable without sacrificing style.

For dressier sneakers, no show socks are one direction you can go if you want your socks to stay hidden, so the focus is on the sneakers themselves.

But if you like to incorporate socks into the style of your outfit, our Duck Duck Moose socks with cushion will certainly give the impression that you have your ducks in a row. Our tried-and-true 1466 Hiker Micro Crew socks in black are a staple in any ensemble. You may need to change your outfit to pursue your 5-9, but you won’t need to change your socks.

Why You Shouldn’t Go Sockless

It might seem tempting to skip socks altogether — especially with shoes like boat shoes or loafers — but trust me, it’s not worth it. Going sockless can lead to blisters, discomfort, and hygiene issues.

Merino Wool socks protect your feet from rubbing against your shoes, absorb sweat, and keep your feet fresh. So, no matter what type of shoes you’re rocking, it’s always better to wear socks that complement the look and provide comfort.

In Conclusion: Choose Comfort & Style

Whether you're dressing to impress or just enjoying a laid-back day, the right men’s dress socks, or socks in general, are essential for comfort and style. From dress shoes to sneakers and loafers to boots, choosing socks that match the occasion, the season, your shoes, and your lifestyle will ensure you're always on top of your game.

And with Darn Tough Socks, you get not only the perfect fit but also a lifetime guarantee, ensuring your socks last as long as your style does.

About the Author

Dana received the ‘Best Dressed’ superlative in his high school yearbook. Since then, he’s be found wandering the Green Mountains in camo and fast sunglasses. Style is what you make it.