The Tomboy’s Guide to Wearing Socks with Dress Shoes


So you’ve got yourself a dapper pair of oxfords, derbies, or other swanky masculine dress shoes. Whether you’re a formal shoe newbie with your first pair or an old pro with a closet full of fancy footwear, the myriad rules about what socks you’re not supposed to wear with dress shoes can be a bit mystifying and overwhelming. We’re here to clear some things up and lay out the laws of socks and dress shoes for you, so that you go into the fashion races armed with knowledge.

Even if you’re the sort of person who flaunts convention, charging into life with one neon green ankle sock on your left and a greyscale houndstooth business sock on your right, it’s handy to understand what the business world sock standards are. After all, they always say you need to know the rules before you start trying to bend them.

 

The Three Essential Rules of Socks and Dress Shoes 

1. Never wear white socks with dress shoes

“But what about if – ” No. Don’t do it. White socks just don’t look good with dress shoes of any color. Even light brown dress shoes, which you might be tempted to wear with white socks, are cheapened by the presence of plain white socks. And always avoid the ultimate fashion sin at all costs: white socks with black shoes and black pants. (Are there exceptions to this rule? Yes, sometimes. But if you’re not sure, then that probably means white socks aren’t suitable.)

2. Never wear solid black socks with brown shoes

We’ve talked a bit before about the poor pairing that is black and brown in close proximity. If you add patterns to the mix, that can change things a little, but as a rule you should just avoid this combination. It’s infinitely easier to mess up than it is to pull off. Attempting the black and brown pairing is for master class fashionistas, and if you’re not superbly confident in your understanding of color theory, it’s just simpler to avoid it entirely.

3. In formal situations, always match your socks to your pants

There is room for creativity in sock selection, but you shouldn’t go there if the occasion you’re dressing for is extremely formal. For things like business meetings, funerals, and any situation where your outfit should convey respect and sobriety, follow this simple rule and you’ll be golden: whatever color your pants are, that’s the color your socks should be. That means grey socks with charcoal dress pants, dark blue socks with dark blue dress pants, black socks with black dress pants, and brown socks with brown dress pants. If you just want a hard and fast rule that will never steer you wrong when choosing socks for your outfit, this is the one to go by.

 

Fun and Acceptable Ways to Bend the Rules with Socks and Shoes

Okay, you’ve got the basics down of what never to do. What about some ideas of what you can get away with if you’re feeling like matching perfectly to your pants is fifty shades of boring?

 

Matching Colorful Socks to Accessories

Super bright, solid-color socks are a statement. They say clearly, hey, I’ve got some personality! Don’t mistake me for a nine-to-fiver!

Your all grey or all earth-tones outfit may feel a little drab for some occasions. You can spice things up by wearing a bright sock with a matching accessory, like a watch, tie, or necklace. Socks are often overlooked as tools for unifying an ensemble, but they can go a long way as color number three to really allow you to do something fun without it feeling lonely.

With a buddy accessory, you can take a monotone outfit and add some vibrant pink, playful turquoise, or bold red socks, and feel confident that – with another item in your outfit in the same or similar color – you look cleverly put together and aren’t doing a disservice to your fancy dress shoes.

 

Wearing Patterned Socks with Dress Shoes

It’s important to distinguish between traditional patterns and non-traditional patterns. Traditional patterns encompass things like argyle, stripes, and small dots, and are easy enough to find in multi-packs of nice thin dress socks in a variety of base colors. Non-traditional patterns often defy description – they can be everything from repeating patterns of stylized hammerhead sharks to abstract geometric shapes in neon colors.

 

Pictured above on left, Instagram photo by @kalesbug, pictured on right, Instagram photo by @saraaahledford

 

Traditional Patterned Socks

It’s a great way to get started on having a snappier wardrobe ready to take on any fashion challenge by picking up some of these packs of classic patterned socks. The same basic rules apply, that you want the rough match of colors to your pants. If you have black pants or charcoal pants, an argyle pattern with a grey and black base with some elements of red or blue will pair excellently with black shoes. If you’ve got some fun shoelaces to pick from, you can even match the small flourish of color in your classic pattern to a pair of shoelaces in the same tone.

 

Non-Traditional Patterned Socks

For the braver and bolder among us fancy dress shoe wearing types, the most appealing patterns are the non-traditional patterns. In today’s bustling e-commerce marketplace, there’s no end to the options of fun, flashy, amusing socks out there – and who says you can’t pair them with some upscale oxfords? There are companies like Sock Fancy that offer a subscription service so that you never run out of interesting socks to rock, and an endless number of Etsy stores offering cool one-off patterns crafted by self-employed designers for truly one of a kind ankle artwork.

So how do you wear a nice, classic dress shoe with one of these wild, wacky sets of socks? Remember the three basic rules, and you can’t go wrong. Black and brown don’t match, all or mostly white socks don’t work with dress shoes, and whatever colors are in your socks should be reflected in your pants or else in another element of your outfit.

Can you do away with that last rule and wear, say, green and pink zigzag socks with brown shoes, blue jeans, and a white dress shirt? Well… sure, but do it knowing that this is very much a statement piece, and expect to have conversations with people about your sock selection. If you’re comfortable with causing a stir, then get ready to suit up and take the world by storm in your eye-catching sock-shoe combo. If you want to go wacky but balance it and elevate it without neutralizing it, add a small splash of matching colour like – for this example of the green and pink socks – a solid green bowtie. It may surprise you how much people are impressed by courage when it comes to fashion choices in semi-formal situations like highschool reunions or wedding receptions. Maybe don’t wear it to your job interview, though.

 

Wearing Textured Socks with Dress Shoes

You don’t have to show up to the office on Fridays wearing red and blue socks emblazoned with the Star Wars rebel insignia to inject a bit of visual interest into your outfit. One excellent way to give your wardrobe some variety – and to keep your toes toasty in the winter time – is with some thicker socks, usually wool, that have been made with various textures.

Because the shape of the material creates a three-dimensional pattern that depends on shadow and highlight to really pop, you should wear textured socks that are solid colors a shade darker or lighter than your pants. Keep greys with greys, blacks with blacks, blues with blues, browns with browns – but feel free to also experiment with textured socks in subtle colors, like ochre red, olive green, or even dusty orange.

Just remember that these socks tend to be thicker, longer, and heavier than standard dress socks, so prepare for them to make your shoes feel a bit tighter, and be aware that buying them a bit too big means they may slide down and bunch around the ankle.

  

Going Sockless with Dress Shoes

Dodge the question of which socks to wear by not wearing any at all? Yes, it can be done! It isn’t always appropriate, but if you’re planning on being out and about in the summertime, you can often get away with going sock free entirely. Obviously the ideal situation for this style choice is on a private yacht after closing an important deal, leaning back with your martini in one hand and the top button of your patterned dress shirt undone. If that doesn’t sound like an environment you expect to be dressing for, relax – the sockless look can work for situations like having coffee with a business contact on a summer afternoon, too.

Make sure the pants you choose to wear with this look leave no more than two inches of skin showing when you sit down, otherwise it’ll look like you have pseudo-capris on – which would be a strange choice. Otherwise, you want to go all the way in the other direction and wear shorts and maybe a short-sleeved collared shirt, preferably in a light color with a belt that matches your shoes.

Be aware that choosing to go sockless may lead to some unpleasantness like blisters and stinky shoes, since most dress shoes are designed with the expectation that you’ll wear socks with them. Prepare for these hurdles by studying up on how best to deodorize dress shoes, and maybe picking up some cozy anti-bacterial inserts.


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