We discuss dress socks and how you combine them with shoes and pants, so you’ll look dapper and stand out from the crowd.
After we filmed our in-depth dress sock guide, people asked us “Well, how do I combine socks with black pants and brown shoes?” There are lots of basic rules out there, we’ll go through them and afterwards we’ll show you some advanced ways to pair socks with shoes and trousers.
Basic sock rule #1:
Never wear white tennis socks unless you’re at the gym or involved in any other kind of physical activity. No matter how casual, white socks are only good with shorts and never with long pants or slacks.
Basic sock rule #2:
Get a quality pair of over the calf socks because they will stay up and not slide down and not expose your hairy calves. If you’ve worn short socks all your life, switching over to over the calf may seem like an alienating or daring task but once you’ve worn them and earned your first compliment, trust me! You’ll want to wear them all the time.
Basic sock rule #3:
Match your socks to the pants you wear, not to the shoes. Now, while that sounds like a very simple rule, it’s easier said than done. Most men out there either have black, navy, or charcoal socks. Unfortunately, those shades hardly ever exactly match your pants.
Look at this brown spectator shoes with brown socks and brown pants. Now, if you’re close in color to the pants but they’re just in a different shade, it looks terrible.
For that reason, solid colored socks actually pair best with patterned pants such as houndstooth, or glen checks, or stripes.
If you wear a lot of solid pants, you can still wear solid socks, just make sure to pick a color that is quite contrasting so overall, it looks quite appealing.
For example, look at this combination of khakis with dark green socks and brown shoes, looks great, doesn’t it?
Advanced ways to pair socks with shoes & trousers
How to pair socks with solid Pants
Most men have them and the best kind of sock to wear with them, in my opinion, is a two-tone sock. The advantage of having two colors is that it basically creates a third in the middle and that’s even more like a gradient, so it works with all kinds of blue pants, and navy pants, and it will always look good.
To show you the power and the versatility of one single two-tone sock, let’s take a closer look at these combinations wearing the charcoal and orange shadow striped socks from Fort Belvedere.
- First of all, I can wear it with brown because the third tone between charcoal and orange is a kind of brown. I’m wearing them with suit slacks in mid-brown with a split toe derby shoe, and I can also have them with spectators. Looks great, doesn’t it?
- Because the sock is charcoal, it works with all kinds of gray, including charcoal or light gray because again, the gradient of orange makes it work with all shades. It works with charcoal slacks with black shoes; It’s a very business appropriate combination, and you could easily pull it off at the office. Alternatively, you can take the same slacks and the socks and pair them with an olive green pair of shoes for a more casual look in a more relaxed office environment or on a Friday happy hour.
- The same pair of socks works with khaki pants or off-white pants and spectators. It still looks good.
- You can also pair them with black pants or navy pants, and tan shoes.
- It also works well with brown monk strap shoes and green corduroys; alternatively, you can wear it with sand chukka boots as well.
As you can see, this single pair of socks is so versatile that it can be literally worn with 2/3 or more of your entire wardrobe.
Now, let’s look at it the other way around. Let’s assume you have a navy pair of pants, and you want to combine it with different socks to create a different look. The advantage is that you can have just one or two quality suits to create different looking outfits. With socks, they’re much less expensive than an entire suit.
- For example, you can combine blue and red socks or burgundy and red which is a little more subdued with a combination of oxblood shoes and navy pants.
- For a slightly different look, you can do navy and yellow striped socks with black shoes, or olive green ones if you want. As you know, the mix of yellow and blue can create this green and so, you can use an olive green shoe that works just fine even though there’s no green in the sock or in the pants.
- If you are in a traditional office environment and you want to be less bold, go with a navy and blue shadow striped sock because it literally works with any kind of blue or navy. It’s different enough to be unique and stand out in a very subtle way, but it’s perfectly office appropriate even in traditional white collar environments.
- If you want to spice up the look of your navy pants, you can go with red, or you can have blue and yellow, or maybe go with light gray and light blue. With a classic black Oxford, it makes for an unusual business outfit.
- On the other hand, you can use the same pair of socks and pants and pair them with a brown pair of double monks for a more contemporary look. You can pair them with a derby shoe to make for a very versatile travel outfit.
- Of course, you can also use a pair of bold royal blue socks with a clock pattern to make a bold statement.
No matter what pants or shoes you have in your wardrobe, having a range of different socks helps you to really create a number of different outfits and it’s much less expensive than buying either shoes, suits or pants. The opportunity of creating different outfits just by changing your socks is endless.
On top of working really well with solid pants, those shadow stripe socks also work supremely well with patterned pants. The only time it doesn’t work is when you have a striped suit that has about the same width as the socks because then it looks confusing. If you have a fine stripe, a white flannel chalk stripe, a glen check, a houndstooth, tweed, or any other classic pattern, the shadow stripe socks will work.
Ideally, you pick one color that’s slightly similar and one that’s contrasting. On top of that, you can also decide to match your socks to a different accessory such as your pocket square, your boutonniere, or your tie. For example, the blue and red socks would work really well with the navy and red knit tie. Sometimes, people also pair their sock color to the lining color of their suit which can also look quite stunning.
Another advantage of two-tone socks is that you can actually match the color mainly with the shoes rather than the pants. Like this combination of burgundy derby shoes with a burgundy and stone colored stripe shadow striped socks from Fort Belvedere paired with khakis. Looks awesome, doesn’t it? Of course, the colors are not exactly the same, but you have that third undertone that ties everything together.