Pick a Pair

With a wealth of options on the men’s underwear market today, how do you pick a pair and stick with it? Well, there are a few considerations to keep in mind before committing to a set. Let’s discuss what goes into picking the perfect pair of underwear for any occasion.

Wear a Pair or Nothing Down There?

The first choice to make when picking a pair is… well, whether you’re picking a pair at all. Going commando is definitely an option: many people choose to go without underwear for a variety of reasons.

Going commando means you’re less likely to have issues with sweat, as there would be maximum airflow downstairs to keep everything cool and dry. This can also help with your sperm count if you’re concerned about that; recent research suggests that tight underwear can have a negative effect on fertility because of the excess body heat your testicles are exposed to. Still, that effect is minimal at best, so it shouldn’t be a driving factor in your decision. You might also opt to go commando if you’ve found underwear to be restrictive in the past, and have had issues with chafing and bunching that make certain styles of clothing uncomfortable to wear.

That being said, there are plenty of reasons to wear underwear, and they tend to outweigh the alternatives. Chafing is far more likely when you’re opting for no barrier between your legs or your bits, which can cause irritation and discomfort, especially when it’s hotter. It can also be dangerous to go commando: freeballing in high-activity situations can lead to twisting, pinching, crushing, or, in a worst-case scenario, testicular torsion. Beyond that, you have a nightmarish chance of catching something important in the zipper of your fly. Also, freeballing means that you’ll be having direct contact with your pants, which you likely don’t wash as often as underwear. You may also have issues with embarrassing, hard-to-clean stains or spotting. 

So, while you can go commando, it’s probably not the best idea outside of lounging around the house.

What to Consider When Picking a Pair

You’ve opted to wear a pair of underwear with your outfit, so your next step is choosing the right pair to go for. Here are some factors to consider when you pick a pair.


A large part of your consideration for which pair of underwear to reach for should be the occasion for which you’re wearing them. Different cuts and styles are good for different types of activities. 

  • Boxers are excellent for sleeping and work well under pleated pants and wider-leg slacks. They’re airier, which means less chafing, and easy for sitting (such as at an office job). However, they do tend to bunch, which can be uncomfortable if you’re moving around a lot and unseemly if you’re wearing well-fitting pants. 
  • Briefs are better at keeping everything contained, especially if you’re wearing lightly fitted pants like jeans. They don’t bunch when you move, which makes them more comfortable for any kind of physical activity. That being said, they sit close to the skin, which can cause chafing if you’re sensitive.  
  • Boxer briefs are both snug like briefs, keeping your bits in place, and extended like boxers, meaning you’re getting less chafing. They also don’t tend to bunch, which is good for physical activity. Still, they’re not great to wear under fitted clothes and can be restricting on the legs. 
  • Thongs, G-strings, and jockstraps are perfect for tightly fitted clothes like skinny jeans, and they’re the option to go for if your activities are going to be sexier. Don’t plan on wearing them too long, though: their rear strings can be uncomfortable, especially for newbies, if they ride up.


You’ll want to make certain that you’re wearing the correct size of underwear too. Generally, your underwear is going to sit slightly below your natural waist, so about where your pants’ waistband sits slightly above the top of your hips. Some cuts, however, will sit at your hips, so you may need to measure twice. 

  • You can find your waist measurement by finding the thinnest point of your torso (normally, this is just above your belly button, but this can change with your body type) and measuring around it. Make sure your measuring tape is even all the way around for the best results. Don’t suck in your stomach or hold your breath while you’re doing this, by the way — you want a natural measurement for the best fit. 
  • You can find your hip measurement by finding the widest part of your lower torso (somewhere just above your bits) and measuring around yourself. A hint for this measurement is that many of us can feel our hip bones. Feel for the top of the bone at your side by lightly pressing, then measure around the top of the bones.

Whichever measurement you choose to use will usually correspond to the sizing chart for your brand of choice (in inches for American brands and centimeters for international brands). Pick the sizing option closest to your measurement; if you’re in between sizes, opt to go a size up for more comfort. Better to have a little extra breathing room than to feel restricted.



The fabric that your underwear is made of can make a big difference in how it looks and, more importantly, how it feels. 

  • The most common option is cotton, a breathable, strong, natural material that is easy to wash and lasts a long time without special maintenance. It’s great for hotter environments, as is linen, but linen tends to be a bit rougher on average. 
  • Spandex and polyester are often used in blends with cotton, and can make your underwear more flexible; unfortunately, they don’t last as long as pure cotton and can be less breathable, making them more uncomfortable in hot or active environments. 
  • Silk is a popular choice for luxury undies and those designed for sexier uses; it’s famously soft and smooth and can be great for your skin, as it doesn’t cause much in the way of chafing or irritation even when relatively tight. It is, however, very difficult to maintain and easily ruined by water. It’s also one of the most expensive materials underwear can be made of, making it harder to obtain or replace. Therefore, silk is usually reserved for special occasions.


Choosing your color options is largely up to personal preference, but we do have advice.

If you’re planning to wear thinner, lighter-colored clothing (such as linen pants or similar items), don’t opt for plain white underwear. The stark contrast between that and your skin will make your pair very visible under your clothes. Instead, opt for a neutral color that is as close to your skin tone as possible. Tans, browns, and grays are good options depending on your skin tone. You may also want to avoid patterns, as again, the contrast can make your undies more obvious.

For darker-colored thin clothing, opt for a darker shade or even black; too light of a color will show through. You might be able to get away with patterns in darker-colored clothes, as long as those patterns are also relatively dark in color. As a rule of thumb, it’s wise to have a look at your backside before you step out, just to be sure.

Thicker clothing isn’t a problem, though; in that case, choose whichever colors you like! Still, we recommend keeping at least a few pairs in each standard color: nude, white, black, and gray.

Where to Find Great Pairings

There are lots of options for finding great underwear, both in-person and online.

In-person, you can find okay underwear at quite a few  clothing stores, but the higher-end brands and more durable pairs are going to be available through department stores or specialized men’s clothing stores. In-person shopping is great if you’re wanting to test your fit before you commit, but can be frustrating for men with bigger body types (above XL, for example) as options and stock tend to be limited.

Online shopping means that you have a chance to compare prices across a range of different stores. You also have far more options to choose from in terms of style and sizing. With access to a wider variety of brands online, you can mix and match your preferences as well as have pairs shipped directly to you, which is hugely convenient. Still, you won’t be able to try anything on, and you’ll likely need to pay for shipping. You will also often have a long wait time between purchase and wear, which can be extended if you need to make a return or exchange.


Looking for great underwear with regular updates to your wardrobe? A convenient way to test-drive new brands and styles while building out a staple closet is entirely within reach. Meet our subscription box


We’ve taken the confusion out of picking your new pair. Tell us what you like and we’ll curate a box of underwear from some of the best brands on the market and ship ‘em  directly to your door. You can pick your frequency as well, so that you always have a new set when you need it. 

Read More: Picking a Pair

Read More: Andrew Christian Guide

Read More: Celebrity Underwear Guide