Men’s Dress Sock Guide

The Men’s Dress Sock Guide

Being a gentleman requires many things. One of them is attention to details. Nothing about your outfit screams “I am an amateur” more than wearing white socks or short socks with your suits that expose your ankle because true gentlemen wear over-the-calf socks – always. 

Why? Because exposing one’s more or less hairy legs is nothing anybody wants to see in public. But what exactly are the right socks for you? You have plenty of options on the market. Unfortunately, most are too short and just reach mid-calf. The only way to keep them up is to use sock suspenders that connect your shirt with your socks or sock garters that sit on your calf. Not only is that uncomfortable to wear but you can see them through the pants when you sit.

In today’s guide, we discuss everything you need to know about men’s dress socks, so you look your best while being comfortable. First, let’s start with sock history, highlight the hallmarks of quality Socks, the types of dress socks, Sock Etiquette and How to Buy Socks.

The History of Socks

Dating back to prehistoric times, cavemen skinned animals and used their hides to wrap around their feet. Tied at the ankle, they would use the warmer and more comfortable parts of the animal skin mixed with fat and sometimes the meat. The purpose of these rudimentary socks was, of course, to keep the feet warm, but also, protect them from the harshness of the rougher hide and natural fibers used as shoes. Of course, for those who didn’t properly sanitize the hides or used raw meats and fat, the ability to contract more disease through open wounds would prove for many to be catastrophic and sometimes, even deadly.

Cavemen probably invented the basic idea of socks or stockings, but over years, they progressed into a far more advanced form of protection, offering comfort and separating your foot chafing in the shoe.

King Henry VII Showcasing his Legs using Socks

Socks = Luxury in Medieval Times

By the medieval times, socks were considered a form of luxury and as such they were reserved for nobility. Also, it wasn’t unusual for knights to wear socks underneath the suit of armor because it created a layer of comfort and prevented diseases.

Starting in the 17th century, even regular families could afford socks. Of course, the yarn was often homespun and the socks hand-knitted from itchy wool. On the other hand, the upper-class echelon of society preferred fine silk and cotton socks.

Sock Knitting Machines Bring Prices Down

Once sock knitting machines were invented in the 18th century, prices for socks decreased and the knit got finer. At first, socks were knitted flat and then they were sewn together, leaving a seam at the back side of the calf. For example, the Fort Belvedere Cri de la Soie knit ties are knitted on more than 100-year-old sock knitting machines which have been repurposed for silk knit ties.

Machine kettled sock that is flat

Machine kettled sock that is flat

The First Circular Sock Knitting Machines Appear in the 19th Century

The next big advancement was a circular sock knitting machine, also referred to as CSM. The big advantage was that it was now possible to knit a seamless tube. Of course, the heel and toe areas had to be knitted separately and closed off by hand. Then, in the dawn of the twentieth century, nylon socks came into play and changed the world of male socks and stockings forever.

Vintage Corona Schubert Sock knitting machine

Vintage Corona Schubert Sock knitting machine

In the beginning, the number of needles was limited to 72 which resulted in a thicker sock. Over time, the number of needles was increased and today you can find socks made on machines with 280 needles which represent the finest you can buy in the world.

Nylon Changes The Sock Game

In the dawn of the twentieth century, nylon socks saw the light of day and changed the world of male socks and stockings forever because it enabled the production of superfine socks. Even though the term hosiery and stockings are now associated with womenswear only, over-the-calf socks used to be called hose, and the term was used exclusively for the male socks. Fine hosiery often with embroidery such as clocks were a staple in every gentleman’s wardrobe. Nylon was the new thing at the time and hence it was used in blends most often.

Today, Nylon is considered to be a cheap material that makes your feet sweat and even though it provides strength it is preferable to use more breathable natural materials such as 100% cotton, or wool, cashmere and silk blends. Of course, the area around the calf requires a flexible material that keeps the socks up, but it wasn’t always like that.

Socks Become Fashionable

In the past, socks were secured at the top, not with an embroidered ribbon or string. As socks continued to take on a more traditional and fashionable role, the elegant dandies of France and London would begin wearing intricate socks, stemming away from the embroidery and moving into patterned socks with formal wear that ranged from height right around the calf to the upper thighs.

duke of edinburgh breeches watermarked

Duke of Edinburgh with breeches and silk socks

They are especially stylish with breeches when worn for white tie, as you can see in this picture of the Duke of Edinburgh. Today, even regular white tie outfits are so rare that you hardly ever see anybody outside of the theater, reenactment or costume party wear these full hose silk stockings.

Socks Today

Apart from the ever-popular white tennis socks, most men will not have anything other than solid plain or ribbed black, brown or gray socks in their closet. Maybe a herringbone, argyle or birdseye will be the exception but for the most part, that’s about it. Fortunately, it doesn’t have to be that way, and quality over the calf sock are available in subtle, yet unusual colors that elevate every man’s outfit, mo matter if it’s for business, pleasure or evening wear.

Hallmarks of Quality Socks & How To Buy Them

1. Over-The-Calf Socks Must Stay Up

The most important quality hallmark of an over-the-calf sock is that it stays up. Unfortunately, most socks don’t because they are not sized properly and lack the correct length and materials, which causes the sock to slide down.Therefore, many companies try to offer all kinds of sock suspenders and sock garters, which are uncomfortable, expensive and they show through the pants.

More importantly, it doesn’t deal with the problem at the root and focuses on remedies for bad products. Instead, if you buy good quality socks in your size the first place, because they will stay up, and you can skip any suspenders and feel comfortable too.

Sock Suspenders

Sock Suspenders are gimmicks and not recommended – instead, get a good pair of over the calf socks

Instead, buy good quality socks in your size the first place, because they will stay up, and you can skip any suspenders or sock garters and feel comfortable too. Apart from that, just picture yourself how you have to take off your sock suspenders when in company – it looks utterly ridiculous. Therefore, invest in quality over-the-calf-socks that stay up.

I had to deal with sliding socks for years, and therefore, I decided to create my own. After extensive testing for 24 months, I am now proud to offer you Fort Belvedere Socks that stay up all day, because we put a lot of thought in the materials, the construction, elastic and length of the socks. Therefore, they even stay up after you wash them a few dozen times, whereas all other socks I tried, start to slide down your calf after a few washes. If you are not convinced, read our customer’s reviews and buy just one pair to start. I am confident that you will come back for more.

one size fits it all socks

One-size-fits-it-all socks should be avoided because they never fit

2. Buy Sized Socks

Most companies offer one-size-fits it all socks, which requires the use of flexible artificial fibers but just like shoes come in different sizes, quality socks do too. Although socks are more flexible than shoes, one or two sizes make for an uncomfortable walk, and whenever you see less than three sizes offered, you should not buy from them. Instead, look for suitably sized socks because they hug your foot without leaving pressure points and once you put them on, you don’t want to go back. This is especially true if you have small feet or large feet because most normal socks will either be far too big or too tiny!

For a selection of socks in 4 sizes, click here.

3. Go For Natural Fibers

Natural fibers are more expensive than artificial ones but their ability to absorb moisture is much higher, and you are less prone to sweating in them. Of course, not all cotton, cashmere or wool is alike and for the best quality yarn, you need the longest and finest fibers. Not only will that result in a more luxurious tactile feel and touch but the socks will also last longer and pill less, than regular socks. Of course, cashmere feels very soft, but 100% cashmere socks will not stay in shape for more than a handful of washes, and they must be blended with other fibers to be useful for a while longer. Of course, they are usually worn out faster than long staple cotton socks or long fiber wool socks.

Note, the toe and heel areas may have a small percentage of nylon even if they can be legally described as 100% XYZ. Also, the cuff on top must be elastic and is often made of Spandex or other elastic materials that grab your calf. Rest assured that your skin touches just natural materials.

Interwoven made interesting socks in the U.S.

4. You Want Thin Elegant Dress Socks

When you are at the gym or on a hike, it is ok to wear thicker socks that are cushy. However, with a suit or a combination, a finer sock looks much smarter, and it is also more elegant. Therefore, you should avoid thick tennis-style socks at all times when you dress up.

5. Smooth Toe Area For Comfort

Most socks are machine knitted, but the majority of machines cannot link the toe area neatly, which is why this often requires a separate step. When done by machine, you can often feel it when wearing them, and hence, quality socks are hand linked most of the time. Lately, modern machines have been introduced that can link the toes with a flat result, but those are expensive and thus rarely in use. Therefore, make sure to get only socks with a smooth toe area for comfort. All Fort Belvedere socks are super smooth and hand linked.

How To Combine Socks, Shoes & Pants

The golden rule of sock matching is to always match them with the pants/trousers, not your shoes!

Of course, that won’t always be possible because the colors of your chinos will rarely match your beige socks exactly.

If colors are similar but not exactly identical, the look is off. Instead, it pays to use a slightly contrasting color, or better yet a pattern. Classic designs include herringbone, houndstooth or my personal favorite: ribbed stripes

Ribbed socks are more expensive to produce that flat-knitted socks, but they are also more flexible and adapt more nicely to the foot. Over the last ten years, the dress socks I have worn 80% of the time are shadow striped ribbed socks, because they work with everything and always look smart.

So what are shadow stripe socks? They are socks where the ribs have a different color as the rest of the socks. The advantage is that one sock has two colors that complement each other and as such you can pair them with many outfit combinations.

Matching socks with trousers will be an entire article of its own, but it pays to understand the concept.

For example, a  beige Chino looks great with brown shoes and a burgundy sock with a beige stripe. A burgundy sock on its own would be too dominant, but the softer beige stripe pulls it together nicely.

Now, let’s say you have a navy suit, you can wear it with navy and red striped socks. Even if the nNavy of the socks doesn’t match the blue of the suit, it will still look handsome because the combination of red and blue catches the eye, without being overly loud. As such, one pair of socks works with all of your blue suits. If you just had solids, you would either need a perfect match or a shade that is clearly different. If they colors are too close, you cannot combine them. On the other hand, striped socks work with a lot more outfits.

Like this guide? Learn even more with our ebook. $25 or FREE with purchase of 3 pairs of socks

So, it’s summer now, and you have a light blue chino but also a mid-grey, light gray or charcoal suit. You can wear a pair of light-grey and light-blue striped socks that work well with all of your trousers without being boring. If you prefer a stronger contrast, try dark gray and turquoise stripes.

In case stripes or patterns are too bold for a certain occasion, you should think about getting solids with clocks because they combine the understatement of a solid pair of socks with the elegance of a gentleman. The small vertical pattern on the side of each sock is very subtle but different from the stuff you can buy at normal men’s stores or Amazon.


Pink grey - brown green - teal purple -navy yellow over the calf Ribbed Shadow Stripe Mens Socks 100% Cotton- Fort Belvedere Made in Italy

Pink grey – brown green – teal purple -navy yellow over the calf Ribbed Shadow Stripe Mens Socks 100% Cotton- Fort Belvedere Made in Italy

Dress Sock Etiquette

Of course, you will always find exceptions to the rules, but these are basics that help you maneuver the waters.

1. Don’t wear bold, bright patterns with Black Tie or White Tie

For black tie or white tie events, a pair of black or purple socks might be daring, but they are certainly loud and will make you stand out no matter if you want to or not. Traditionally, evening dress socks are made of silk or silk blends, and they should match the trousers. The finest evening socks for black tie you can get are knitted on a machine with 280 needles and so thin soft and elegant that others will be jealous.

2. Don’t wear athletic socks with business attire or formal wear.

Athletic socks are for active wear. For anything remotely dressy, go with over-the-calf dress socks. End of story.

3. Pair Socks With Your Outfit

As discussed above, it pays to choose socks based on your trouser color. But if you have a pair of striped socks with two colors or just a contrasting pair of socks, it pays to pick up that same color somewhere else in your outfit. It could be your pocket square, your tie, bow tie or even shoelaces. No matter what you choose, having some form of coordination will make your outfit look quite debonair.

hole in sock

Holes in socks are a sign of sloppiness and reason for embarrassment – exchange your socks once they have holes

4. Avoid ripped or Punctured Socks

If your socks have a hole, it’s time for them to go. Surely, if you have someone who can fix them you might want to give that a try, but at the current cost of hand-labor, mending can easily cost more than a new pair.

Replenish your collection on a regular basis but if you invest in quality, and you have 12 pairs or more in your rotation, socks should last for a while.

5. Trim Your Nails & Treat Your Heels

Your socks will last much longer if you properly cut or clip your toenails and file them afterward to avoid sharp edges. The same goes for your heels. If you have crackly, hard calluses on your heel, they will wear out your socks more quickly than if you take care of your heels. Hence, take care of your feet with a quality nail kit.

6. Don’t Mix-And-Match Them

Socks come as a pair for a reason. They are not intended to be mixed and matched. Even a basic black sock can be a slightly different shade or hue than the other. Always be extra careful to keep your socks paired correctly, or discard them if they’re not.


Dress socks can be complicated because they often are not sized properly and slide down your calf. However, if you invest in quality over-the-calf socks that are sized for your foot and height, you will be comfortable all day. On top of that, if you invest in a number of two-tone striped and solid socks or socks with clocks, you can easily cover your entire wardrobe while adding a unique accent to your wardrobe.

Men's Dress Socks & Over-The-Calf Sock Guide
Article Name
Men's Dress Socks & Over-The-Calf Sock Guide
Ultimate Guide To Dress Socks in over-the-calf length that don't slip or slide down including history, sock etiquette & Sock Shoe Pairings
Gentleman's Gazette
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25 replies
  1. Denys D. says:

    Very informative piece of history and advice. However, while I understand that you often discourage “sock suspenders”, the image that you show above is actually the one of shirt stays, despite that both can serve a common purpose of keeping the socks up (which is the part you don’t recommend) and the shirt tucked in. As for the latter, I still think its use is well justified to keep the shirt from forming a muffin top above the waist during the day, even with properly fitted shirts, when you sit and stand, bend and extend. For this reason I believe these are still very much used in the military (I am deferring on this one to Antonio Centeno). Lastly, speaking from my personal experience, any time I dress up, especially for a festive occasion, by putting on the shirt stays and suspenders I feel like I can safely forget about how I look and focus on what I am doing, and still look like a million dollars.

    • Sven Raphael Schneider says:

      Of course were are familiar with the other sock suspenders on the calf etc. but I find them just as useless. Antonio did use them, but I showed him that they were not necessary.

      You can look like a million bucks without shirt holders or shirt suspenders every day. There is zero reason to use them, unless of course, your socks are too short or the shirt does not fit right.

      I would not be caught dead wearing these things for festive occasions especially since they show through and look anything other than a million bucks. But if they make you feel better, go for it.

      • Quentin says:

        Raphael, since you do not recommend shirt stays I would actually like to know what you recommend to keep your shirt from untucking. I agree that shirt stays and sock garters are not a comfortable solution for these things and have a genuine curiosity how you remedy this issue. I appreciate your information on this subject. Thank you.

        • Wyatt Fetner says:


          As a cadet at Texas A&M, we used an elastic baseball belt that would sit along your hips, reaching back to hold down your shirt tail. Trousers would go over this, and the shirt would stay tucked in. While this may not be the most “elegant” sounding approach to keeping your shirt tucked it is very effective.

        • Sven Raphael Schneider says:

          If your shirt comes untucked, chances are is is too short, and the fit is not right. Personally, I never have issues with a shirt coming untucked, but I also go for extra long shirts.
          What exactly is the problem you are experiencing.

          • Quentin says:

            This is something I typically observe when moving from a sitting to standing position. Perhaps I shall look into finding longer shirts.

        • Roger Cushwa says:

          The USMC remedies this by tucking your undershirt inside of your boxers/briefs then dressing. I do this every day and my shirt never “muffins”. I used this trick when I worked a delivery truck and was unloading cases of soft drinks, bending and raising my arms at every stop. Also remember to keep your “alignment” between your shirt seam, belt buckle and zipper. They should form a nice straight line down your front with leading edges to the right side.

      • Denys D. says:

        I see your point, and I do sport over-the-calf socks for all the right reasons you described, and I agree – shirt stays are not the most comfortable things to wear on daily basis, which is why I don’t wear them routinely. But I still disagree with you on that there is zero reason to use the shirt stays (NOT for the sock pulling purpose) on occasions when absolute flawlessness in your appearance matters, for keeping the shirt tucked in on the go. As I have said, even the shirts that are tailored and fit well will get untucked during the long days when traveling, sitting down and standing up, or with reasonable amount of physical activity.

        So I would second Quentin’s question, if not shirt stays, what can I use to keep the shirt tucked? Surely, you wouldn’t suggest excusing oneself all the time to go to the restroom to tuck the shirt back in.

        • Sven Raphael Schneider says:

          Where does your shirt end? In the last 15 years, I haver never had any issues with shirts coming untucked if my tails were long.
          Only if you wear shirts that are too short will you have issues with it coming untucked

          • Denys D. says:

            Sorry, I should have described the situation better. I didn’t mean untucked completely, but rather the excess fabric that is pulled out lengthwise above the pants when, say for example, I bend to tie the shoes. When I stand back up that extra fabric is not going back inside by itself, thus creating a lateral fold or even two above the waist in the back, unless there is something that is pulling it back inside (shirt stays), or else if I undo my pants to straighten the shirt out.

            • Sven Raphael Schneider says:

              Unless you do a lot of physical work, it will likely not be an issue. If it is, I suggest you add a little tab to the shirt front that buttons to the front of your pants, like on an evening shirt, that should keep your shirt nice and neat all day.
              But honestly, if you wear a shirt, wear a jacket.

              • Denys D. says:

                Great idea! I know the tab is present on some traditional black/white tie shirts with a bib, but it can definitely work with regular shirts too, with a little customization. Thanks.

  2. David says:

    Great article..very informative. I disagree a bit about the mid-calf socks and the use of garters..not “suspenders” as you show in the photo.. I have always worn Byford mid-calf with garters..and there is never a problem..nor do the garters show through the trousers. They are comfortable as well. . Thank you for the article.

    • Sven Raphael Schneider says:

      I guess comfort is subjective, and I hate them.
      Why you would choose to put them on if you do not have to is beyond me but if you like them, go for it. I can always tell if people are wearing sock suspenders or not when they are sitting, unless they have very thick fabric trousers that doesn’t show it.
      To me there are only disadvantages but no advantages.
      Bottom line is sock suspenders are superfluous if you have the right kind of socks.
      For example imagine you travel by plane and you have to take off your suspenders because of the metal… what a pain.

  3. George says:

    My problem is, as with most clothing, I require tall or large sizes. Being as my foot is 14 wide, the normal sized sock will not line up with my heel. Do you have suggestions as to big and tall shoes and clothing sources for higher end items? It would be great to see some videos on that subject.

  4. Edward says:

    I am glad that you over many sizes of socks, based on foot length, but I still have to find any manufacturer that offers multiple sizes of over the calf socks based on calf size. I am an athlete and have large calves. Any over the calf dress sock feels like a compression sock to me and it is ridiculously uncomfortable. Just some foot for thought regarding your recommendations. Not everybody has skinny calves

    • mrbukie says:

      Simon I completely agree with you.
      I would imagine a lady seeing these would laugh you out of the boudoir!

  5. tbicksler says:

    Let’s talk Sock game
    I love/hate this whole thread.. If your shirt is an issue, fix your shirt. Socks to me are like a tie.. They’re a statement. And actually in my opinion say more about you than a tie. Done right socks are 2nd to shoes. I promise you if you have the right set(kahonas or socks) socks will get a compliment before those big time $$$$$ shoes do and I wear both.
    You want socks that Don’t fall (only Ive ever worn), great prints & colors. I wear them everyday & have to for close to a year. By far best socks I’ve ever worn!!

    American made and contact me if you’re interested. These are a game changer.

    I gain nothing by this! Just a great sock & company that stands behind them

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