Mens Dress Socks – The 5 Best Socks to Wear on a Date in 2021

You’ve very likely got your own date night routine down pat: A preferred restaurant or activity, a favorite pair of pants to wear, a favorite pair of dress boots laced up – that last part is where mens dress socks come into play. No matter how frequently you hit the town, we’re trusting of the fact that all the little details are taken care of, as a gentleman would do. Your outfit, your set-up, your Old Fashioned, all can be perfectly prepared, but it’s all for naught if you ruin your ensemble with a misstep without mens dress socks that look stylish and perform under pressure.

Pressure, you say? Hey, dating can be a nerve-wracking game at the best of times. If you’re worried about whether your socks match your outfit — and not feeling confident that they in fact do match said outfit — the list of things that can go wrong only multiplies. People appreciate someone who’s thoughtful and well-dressed, not someone with mismatched socks, or socks with holes in them. It sounds simple (they’re just socks, after all), but there’s a reason so many companies have a laser-sharp focus on making mens dress socks with quality, style and performance in mind.

It’s really just about the same as having a pair of rugged boot socks with which to wear your lace-up or pull-on boots: Different socks fit for different occasions.

And other thing: If you end up taking your shoes off in front of said date, and those socks aren’t of proper quality or style? That’s a big “L” in our book. Again, it might seem simple, but socks are an underrated accessory, and the wrong pair can leave your feet hurting and your ensemble limping to the finish line. It’s 2021 though, and mens dress socks are easy to find (if you know where to look), and easy to wear (if you’ve found the right pair).

Dress socks for men should be reserved for, well, dressy occasions. We’ll get into this in a minute, but dress socks are best worn with dark, dressy jeans, your finest suit, tailored chinos or corduroy pants (for example, in the colder months). Dress socks, however, aren’t to be worn with your typical pair of shorts, and it should nearly go without saying that.

Mens dress socks are a bit pricier than your average pair of athletic or casual crew socks, but believe us when we say you certainly do need separate dress socks. It’s really just about the same as having a pair of rugged boot socks with which to wear your lace-up or pull-on boots: Different socks fit for different occasions.

With that crucial separation of work and play in mind (wear athletic socks to the gym, wear dress socks on a date), keep these critical tips at the forefront as you search for dress socks. Figuring out what to wear on a date should be easy: It’s finding the perfect locale that’s the hard part.

What to Look for When Shopping for Dress Socks

  • Search for fine materials: Remember, dress socks should be of an entirely different build and look than your athletic socks. Athletic socks are designed for strenuous pursuits and made with moisture-wicking tech fabrics, but dress socks have a much more fine, thinner weave. The best dress socks are made with anything from merino wool to carefully woven cotton and linen blends. Some are even made with cashmere and feel luxurious on your feet. Each type of dress sock is best worn with dress shoes, loafers or dress boots. Thick wool socks or heavy-feeling boot socks are best left to rugged work boots. And let us reiterate: Save the athletic socks for the gym.
  • Look for versatile colors and patterns: Your typical athletic sock usually is black or white in color, with an athletic logo (among the most common types of gym socks, that is). Here’s another area where dress socks can and should be different. Dress socks work best in solid colors like navy, black or tan (to match your trousers or your suit). Dress socks can also feature a subtle pattern (think small pin dots) or a more bold pattern (stripes, Argyle patterns or an expressive print). Feel free to experiment, but know that finely woven dress socks in a classic color like navy rarely look bad, especially on a fancy, high-stakes date.
  • Be prepared to spend (a bit): With less expensive socks, like everyday crew socks or the aforementioned athletic socks, you typically pay a lower price for materials that aren’t quite as nice as dress socks. With some dress socks, a set of two pairs, or even a single pair, are going to run you a bit more dough. It’s worth it, though: Remember what we said about finely crafted materials and about versatile colors. If you have to spend money on just a couple pairs of dress socks, it’s best to spend slightly more for dress socks you can wear with nearly anything sharp and tailored in your wardrobe.

There’s a subtle art and science to finding dress socks, but it’s a relatively easy formula to get down if you follow the above keys. We think the below mens dress socks hit all the right marks. Your date night style just got upgraded.

The Best Mens Dress Socks for Your Next Date Night

Pantherella Laburnum Merino Wool Socks

Pantherella Laburnum Merino Wool Socks

We could go on and on about how great merino wool happens to be as a fabric. It’s found in T-shirts, loungewear, sweatpants and even shirting. And it’s a staple of some of the finest mens dress socks out there. Pantherella is easily one of the best brands in the game for next-level socks, too. You’ll find ringing endorsements of Pantherella socks on the pages of fashion magazines and Web sites the world over, and it’s the subtle style and fine materials that separate Pantherella from the pack. You really do get it all here, including moisture-wicking, anti-microbial merino wool and an elegant navy color. It also helps that the brand has a long history of using the best materials on the planet, and they offer up enough different varieties and styles (including above-the-knee dress socks) to please even the pickiest dresser. Pantherella is, to keep it simple, one of the most refined places you can go to get mens dress socks.

Joseph Abboud Soft Socks

Joseph Abboud Soft Socks

If you want mens dress socks on a budget, turn towards a reliable and fairly priced tailored outfitter for men. These textured socks, in a grey color that calls to mind, say, James Bond’s suit in Skyfall, are more than reasonably priced, for starters. The fabric blend is soft and ultra-comfortable, and the aforementioned texture finish adds some subtle style beneath crisp grey trousers and black chukka boots. Better still, you can get three pairs for the very agreeable price of $30. They’re what we call the perfect date night socks, perhaps.

Polo Ralph Lauren Supersoft Dress Socks

Polo Ralph Lauren Supersoft Dress Socks

Turn towards an American designer that’s been outfitting the country’s best and most smartly dressed for decades on end. Better still, get some serious bang for your buck with straightforward and versatile mens dress socks, the kind that wear nicely beneath Ralph Lauren chinos or tailored suit trousers. There are three no-nonsense colors and patterns in this affordable pack of mens dress socks, and that’s not all you’re getting. As Polo Ralph Lauren tells it, these carefully crafted dress socks also have a little something extra built right in: They feature an “antimicrobial knit engineered to inhibit the growth of odor-causing germs.” That means your feet will stay cool and odor-free all night long.

Cole Haan Three-Pack Dress Socks

Cole Haan Three-Pack Dress Socks

The excellent thing about searching for mens dress socks is that you’ll often find stylish, reliable pairs in about the same spot you’d find a new pair of dress shoes or sharp sneakers. That is to say, some of the best footwear brands also make easily wearable dress socks for big date nights aplenty. Cole Haan uses a blend of combed cotton and polyester for softness and a nice, laidback amount of stretch. The crisp, dark colorways are also suitably dressy to wear with, say, navy or tan chinos and a white Oxford shirt. Your date night looks are capped off in a way that’s perfectly fresh and modern, especially if you wear a pair of Cole Haan wingtip sneakers. Keep it sharp, cool and classy, right down to your dress socks.

Polo Ralph Lauren 3-Pack Argyle Socks

Polo Ralph Lauren 3-Pack Argyle Socks

Keep in mind that not all dress socks have to be one solid color. In fact, it can be a bit festive and a bit fun (especially around cold-weather holidays or seasonal occasions) to add some pattern to your ensemble. The details, as we always say, make a major difference. It’s also why we’re recommending another pair of Polo Ralph Lauren socks in our guide to mens dress socks. Find a brand you can trust, and then rely on them as often as possible. The use of various shades of tan in this argyle pattern is also a nice change of pace from other colors of argyle socks. We say, wear these with slim blue denim and caramel-colored captoe dress boots for a small touch of impressive, stylish flair on date night.

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Beau is Brooklyn-based style and lifestyle writer. He covers menswear, gear, spirits, craft beer and music. When not writing, Beau can be found shopping for vinyl or sipping on a Brooklyn beer.

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