How to Wear Loafers with Socks, According to Menswear Experts

Socks and loafers can work all the way from casual to professional, but when done poorly, you could find yourself in the dreaded territory of sandals-and-socks wearers.

It’s true there’s a lot of nuance about whether loafers are casual or formal, if white socks are acceptable or fundamental, and whether loafers are even appropriate with trousers. Or with shorts. (There are teams on both sides of the debate.)

These aren’t straightforward “yes” or “no” questions, but in the spirit of not being clickbaity, the simplest rule is to match your socks to your trousers. If you can’t, white socks are a good second option unless you’re trying to look professional.

This guide will focus on how to wear loafers with socks and match the to the occasion and the outfit so that you look great no matter what.

Meet our Experts

For advice on wearing loafers with socks, we spoke with two menswear leaders in New York City. The professional tailor and YouTuber Alejandro Jomar joined us for our video discussion in our Queens studio.

We also spoke with Justin FitzPatrick, owner of J. FitzPatrick Shoes and founding editor of The Shoe Snob Blog. Both of these men have spent their careers focused on footwear and style, with Mr. FitzPatrick boasting decades of experience making shoes in Italy, England, and the United States.

And look, we at Stridewise know our stuff too. We’ve traveled the world and met with expert cobbler, shoemakers (they’re different things), and historians to get the best and most relevant advice we can to help guys dress their best.

Can You Wear Socks With Loafers?

• You can wear socks with loafers, and it’s a lot more comfortable than going barefoot or with no show socks
• Standard advice is to match the socks to your trousers, but that guideline is flexible when you’re dressing down
• White socks are a good option for informal use
• White or cream crew socks are the best for wearing with shorts (though we admit that the sockless look may be ideal here)

Simple answer: yes! But there are guidelines. We won’t call them “rules” because we’re not splitting the atom here, not many people care how you go about this. But if you want as many folks to approve of the look as possible, sure, there are some tips you can use.

“I think the more casual you’re dressing, the more acceptable it is to go white socks — or no socks if that’s your preference,” says Jomar. “The dressier you’re going, the more important it is to wear socks that are tone-on-tone with the trousers or, failing that, with the loafers.”

How to Wear Casual Loafers with Socks

• By definition, there aren’t very firm rules around casual wear
• Just don’t wear anklet socks
• Casual environments are preferable if you like the no-sock look
• White crew socks are best for shorts and loafers
• Brown suede is an ideal upper for casual loafers, and look for one with a wider, rounder toe

If you’re in a firmly casual environment, it’s unlikely anyone is policing your sock choice — but anklet socks one hundred percent do not work with loafers. Pick a side: sock or no-show sock. Anklets are a cowardly half-measure!

As the sections in this article progress in dressiness, the “rules” around socks and loafers will become a bit less flexible. At this bottom tier of dressiness, though, you’re free to have a little fun.

“While some ‘style gurus’ tell you to only ever wear socks that match the pants or the shoes, a patterned or colorful sock can make sure people see your outfit as more casual — and that you’re therefore allowed to be breaking that rule!” says Jomar.

Summer Casual: Shorts & No Show Socks

If you like the sockless look — whether that means actually going sockless or just looking like it with no-show socks — it’s best to do it with shorts or casual trousers. Once you’re in business casual territory, it’s time to sock up. An exception might be a summer wedding suit.

Bombas, Ondo, and Sheec make good no show socks, but no matter what the marketing tells you, they’ll slip under your heel at some point — so it really is best to wear socks if you’re doing a lot of walking.

Properly going sockless? Remember that a bit of talcum powder can help if you have sweaty feet, and an unlined, leather soled loafer will the most breathable option.

Black or brown loafers in smooth leather are a little dressy for this use case — the default casual leather is brown suede, though Grant Stone offers a ton of funky leathers in other colors.

The main takeaway for socks with loafers in very casual environments is either white crew socks or no socks at all.

Cold Weather Casual: Anything Goes Except Sockless

Casual clothes in cooler weather means heavier fabrics like denim and canvas, which don’t always look quite right with the breezy sockless look. It’s time to wear socks.

“For casual looks in colder weather, I prefer chunkier loafers, and I’ll wear almost any sock with them,” says Jomar. “The only guideline is the basic one of matching the color palette: if your outfit’s made up of warmer earth tones, do the same for your socks, and the same goes for an outfit with cooler tones. For instance, I’d avoid a grey sock, which is a cooler color, with warm toned trousers like tan or brown.“

Patterned Socks With Loafers?

What about patterned socks? Hey, you’re dressing casual — go for it. Patterned wool socks look great with casual looks, especially if it’s a chunkier, harder wearing loafer. (Our pick for that is Grant Stone’s, which has high side walls, a tough Goodyear welted build, and is just insanely versatile.)

“You just don’t want to add too many details to an outfit,” cautions Jomar. “If you’re wearing patterned socks or white socks, you want everything else to be relatively subdued, and I’d avoid other patterns in the fit.”

Best Socks to Wear with Casual Loafers

Recommendations for Casual Loafers

Should You Wear White Socks with Loafers?

• Better for casual/smart casual than business casual/professional
• Best for simple outfits; don’t add statement pieces

White socks with loafers: controversial? Yes. A bad idea? Not if you do it right. The only two things you should know are that it’s too casual for business casual and that it’s best worn when the rest of your outfit is relatively subdued.

“This is one of my personal favorite looks, and I confidently wear white socks with pretty much anything except the super formal loafers,” says Jomar. “You just want a nice, very simple outfit because the statement of the outfit is going to be the white socks.”

Recommendations for White Socks for Loafers

While it’s tempting to say you can just get any white sock and call it a day, you do want to make sure you’re not getting white athletic socks or boot socks — just because a loafer’s fit doesn’t leave a lot of room for thick socks.

We like Boardroom Socks because they’re American-made by a small business, but we won’t pretend there are no alternatives out there. Just ensure they’re not too thick, and if you plan to wear them with shorts, don’t get them too high, like over-the-calf socks.

How to Wear Business Casual Loafers with Socks

• Try to keep the socks and trousers matching tonally
• Subtle patterns are fine
• Pick a more tapered loafer in a smooth leather

What is business casual? It’s ambiguous, and ultimately it’s all up to whoever is setting that as the dress code. They might prefer you wear a tie or they might allow jeans.

“Business casual is very interesting because the lines are so blurred by the general public between what is acceptable and what isn’t acceptable in the business casual setting,” explains Jomar. “But typically, we want to stay on the side of more business formal dress.”

For work we’re sticking to classics: black or polished brown loafers, patterned or solid socks. You definitely want a collared shirt, and we’re not talking polo shirts here: a cotton button up like an Oxford cloth button down is usually the right balance here, and while your jacket and pants don’t have to match — they probably shouldn’t, that would make it a suit — we like a tie with business casual.

“I stray away from wacky patterns on socks,” says FitzPatrick. “But I’ll do classic stripes, or every now, and then, I’ll make a slightly bold pattern if I’m sure the situation isn’t too far on the ‘business’ side of ‘business casual.’ But I don’t do polka dots or anything that is overly eye-catching.”

Recommendations for Business Casual Loafers

How to Wear Socks with Formal and Dressy Loafers

• Match your socks to your trousers
• Avoid patterns
• Stick to smooth leather loafers, ideally black, and ensure they have tapered almond shaped toes

While loafers reign supreme in smart casual and business casual settings, there are plenty of sleek options in black calfskin that are perfect at home with a suit and tie. And don’t even think about going sockless.

“You must have socks with a suit,” says Justin FitzPatrick. “If you’re in Miami and it’s a cream linen suit and your loafers are brown suede, you could get away with sockless. But in a modern or urban or professional environment, sockless is not an amazing look.”

Most importantly, get dress socks that match the color of your loafers, the same as you would with dress shoes and a suit. And if you can’t do that, match your socks to your loafers.

Examples of dressy or more formal loafers have to do with the type of leather and style. Glossy leathers like box calf and Shell Cordovan are more formal than suede. Horsebit and tassel loafers are usually considered acceptable for business professional, so long as they’re in black leather and taper at the toe — those elements are extra important if your loafers have ornamentation like those models.

One more often overlooked factor: make sure your socks are over the calf socks. This makes sure you don’t show any hairy leg when you’re sitting down, which is a major no-no in formal environments.

Recommendations for Socks to Wear with Dressy Loafers

Recommendations for Dressy Loafers

Conclusion: How to Wear Loafers with Socks

Now that you know how to optimize the socks-with-loafers look, you’re ready for any situation life throws at you. Unless it involves running. That’s hard to do in loafers.

While there are some situations where no socks with loafers is appropriate, there are no situations where socks with loafers are inappropriate.

So whether you’re rocking white socks for a relaxed retro look, patterned socks for a playful statement, or no-show socks for a clean summer look, there’s a loafer-sock combo for most any scenario. Just make sure they’re the right socks for the occasion, or you might end up looking like your dad on vacation —rocking tube socks, loafers, and athletic shorts at the breakfast buffet.

FAQs: How to Wear Loafers with Socks