The Different types of Men's underwear styles

Back in the day, men only had two underwear options: boxers or briefs. However, over the past few decades, many styles of men’s underpants have multiplied, leaving them with way more options and no easy decisions. In this guide, we offer a brief history of men’s underwear styles that explains how we got to where we are today. Then, we dive into the different types of men’s underwear styles and explain how to choose between them.

History of Men’s Underwear

After the fig leaf, the first iteration of men’s underwear was the loincloth, a single piece of fabric wrapped around the hips and pelvic. The loincloth was used in many cultures, from the Minoans to the Aztecs, and could come in many different colors and patterns. The loincloth was often used as outerwear as well as underwear, though it might be paired with a tunic or cloak as well during cold weather. Even today, some native people still wear the loincloth.

In medieval Europe, a new style of underwear emerged called the braies. They originated with Germanic and Celtic peoples and then spread further during the Middle Ages. These loose-fitting trousers could be buttoned or tied and were made out of cotton or linen. They also had a codpiece, or a flap that could be unfastened. This allowed men to urinate without having to completely remove their trousers and underwear, a revolutionary change that prefaced the flap on modern boxers.

The next development came during the Industrial Revolution with the development of the Union Suit in 1868. Originally designed as a women’s garment, the Union Suit became popular with men as well. The one-piece garment featured long sleeves and pants and eventually became known as Long Johns, which they are still called today.

Shortly thereafter, the jockstrap debuted on the scene in 1874. The rise of biking meant that men’s genitals were constantly being jostled by rough cobblestone roads, so a man named C.F. Bennett designed a contraption that featured a supportive pouch held in place with two elastic bands. Today, the jockstrap is still popular among men for playing sports and other physical activities.

We finally reach the age of modern men’s underwear in the 1930s, the decade that both briefs and boxers made their debut on the market. Briefs had an elastic band on both the waist and the legs to hold them in place, while boxers only had it around the waist, featuring a looser leg instead. They both had the Y-shaped flap that is so familiar on modern underwear today. While some changes have been made since then, including many fabric performance enhancements, this is the moment that men’s underwear styles enter the modern age.

Types of Men’s Underwear Styles

If you’re wondering what your men’s underwear options are, here are the main types of men’s underwear styles that you need to know about:


The shortest type of men’s underwear, these have “legs” that end up at the upper thigh and feature elastic around both the waistband and leg holes to hold the underwear in place. Because this type of underwear doesn’t cover much of the leg, they are quite cool to wear during the hot months and provide good ventilation. Men’s briefs provide essential coverage for your private parts and bottom but leave your legs exposed for a slightly sexier look. You also don’t have to worry about the underwear legs rolling up and creating unsightly lines beneath your clothing.

Boxer Briefs

Boxer briefs marry the length of boxers with the support of briefs. They are made of a snug, microfiber fabric that hugs your body and does not roll or bunch beneath your clothes. The classic boxer brief style has legs that end at roughly mid-thigh and is one of the most popular contemporary underwear styles for men. This underwear style is very versatile and works great for the office, date night, working out and everything in between. If you want to combine comfort, style and performance, you can’t go wrong with a pair of boxer briefs in a performance fabric.

Trunk Briefs

Trunk briefs are similar to boxer briefs, but have a shorter inseam and thus provide less coverage on the leg. If boxer briefs are too long for you, but you’re not quite ready to jump up to a real brief, then trunk briefs might be the compromise you’ve been looking for. They are especially good for summer and activities where you know you will be sweating.


Sometimes called midway briefs, these men’s long boxer briefs come almost all the way down to the knee, ending just above the joint. They are a great choice for anyone who wants a little more coverage that reaches down over most of their thighs. If you’re active or like to play sports, briefs are a great option because they prevent friction between your legs. Whereas trunk briefs are a good choice for summer, long boxer briefs are a great choice for winter when you might want a little more insulation to keep you warm. 

Athletic-Style (Closed Fly) Briefs

For many years, men’s underwear styles rarely came without a fly. However, in recent years, this has been changing — and while open fly underwear still makes up a lot of the market, closed fly briefs are rapidly gaining in popularity. As clothing has become tighter, the multiple layers of fabric that a fly requires can show beneath pants, leading some men to opt for a closed fly design. Some men also find it faster and more convenient to simply go over the waistband than to mess with the fly. Closed fly designs also provide more support, holding everything in place as you go about your day, making them an especially good choice for athletic activities. Many men opt for athletic underwear due to its design and material. With advancements in fabric technology, ventilation with closed fly underwear athletic underwear has also become much improved, making it less of a concern. Closed fly briefs are available with multiple different boxer and brief designs, so you find the combination that works best for you.

Compression Underwear

Compression underwear for men offers the ultimate support to keep everything in place while you work out. The tight fabric gives a subtle lift to your package and your bottom without being too restricting, and the slim cut holds everything in place while you move around. Compression underwear is made with advanced fabric technology that will keep you cool and dry while offering these benefits, so don’t worry about ventilation. We also recommend pairing this underwear with a compression shirt as well to help you maintain good posture as you work out.

Padded Boxer Briefs

Looking for a little lift? Get it with men’s padded briefs. Our padded boxer briefs feature removable contour padding to provide a natural lift to your existing assets. They feature breathable mesh cutouts and flat seams that won’t show under clothes or chafe as you wear them. The butt lifting pads can also be removed to turn the briefs into a pair of traditional underwear. Whether you’re looking for something for special occasions or a daily pair of underwear, our padded boxer briefs have got you covered.

Choosing Men’s Underwear

If you’re feeling a bit overwhelmed by all of your options, here is a quick breakdown to help you navigate your choices and select the perfect men’s underwear for you:


When it comes to the style, you have basically three main options: boxer, brief and boxer brief. Remember that briefs offer the least coverage and the tightest fit, boxers offer the most coverage and the loosest fit and boxer briefs fall somewhere in the middle. If you decide on boxer briefs, then you need to choose a length: short (trunk briefs), regular (boxer briefs) or long (midway briefs).

Closed vs. Open Fly

Next, it’s time to choose whether you want a closed or open fly. Some men prefer no-fly underwear, finding that it fits better and offers more support. Others prefer the ventilation and convenience of open-fly underwear. You might also choose to keep a mix of options on hand — for instance, closed flys for during the day and open flys for sleeping.


Now it’s time to choose the fabric. Cotton fabric provides the most ventilation and doesn’t trap sweat and bacteria, making it a go-to choice for everyday wear and sleeping. However, if the cotton does soak up sweat, it doesn’t dry quickly, which is why many men prefer a performance fabric blend featuring polyester or nylon for athletic underwear. You also need to decide if you want compression fabric for your underwear, or if you want underwear made from recycled plastic that’s good for the earth as well as for you.


Finally, you also need to consider whether or not you’d like any features on your underwear, such as pockets, compression or butt lifting pads. While these items aren’t a must, they will upgrade your underwear instantly. If you’re looking to take your underwear game to the next level, then look out for features such as these.

Ready to revamp your men’s underwear drawer? Shop our selection of boxers, boxer briefs and more. If you are having trouble finding your size or choosing a style, please feel free to reach out to our expert consultants or to schedule an appointment with our Personal Shoppers and they can assist you. Orders over $25 get free, fast shipping in the domestic U.S., so load up that shopping cart and you’ll be trying on your new underwear before you know it!