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The Best Men’s Underwear For Every Occasion

Have you ever worn the entirely wrong underwear for an activity? I definitely have.

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It only took one time of going for a long run in silk boxers on a hot summer day to realize that choosing the right underwear is absolutely essential.

If you’re one of the guys who pick just any old pack of drawers off the rack at your local department store, upping your underwear game can be a life-changer.

In this guide, we’ll be covering everything you need to know to choose the best men’s underwear for your lifestyle and activities. So whether you’re already a downstairs fashion devotee, or don’t even know the difference between boxers and briefs, we’ve got you covered.

Best Men’s Underwear For Everyday

Hanes Cool Dri Boxer Briefs

Hanes Cool Dri Boxer Briefs

Getting yourself a reliable, versatile 5-pack of truly comfortable underwear is an investment in work week happiness.

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Hanes modeled these men’s boxer briefs after sports performance underwear, making them tagless, moisture wicking, and with their signature comfort flex waistband.

They’re the real all-rounders of the underwear world: You’ll feel comfortable taking them straight from the office to the gym, or to a night out.

Available at an affordable price and in multiple colors, these are our picks for the best men’s underwear for everyday use.

Best Men’s Briefs

MeUndies Briefs

MeUndies Briefs

When nothing but the absolute softest underwear will do, you’ve gotta turn to MeUndies.

Sporting a space-age fabric known as MicroModal, MeUndies have a cult following for their uber-soft briefs.

Sign up for a subscription with them, and you’ll get a new pair of men’s briefs (or any other style you’d like) in a new pattern each month. It’s a perfect way to keep your nether regions stylish and fresh.

Best Men’s Boxer Briefs

Pair of Thieves Cool Breeze Boxer Briefs

Pair of Thieves Cool Breeze Trunks

Specially designed to keep your goods cool and dry, these boxer briefs from Pair of Thieves are supremely breathable.

With a moisture-wicking, 4-way comfort stretch, they just might be the most luxurious underwear in your closet. Awesome underwear like these are as suitable for the tennis court as they are for a day in your desk chair.

Best Boxer Shorts for Guys

Saxx Ultra Free Agent Boxers

Saxx – Vibe Boxer Briefs

Nobody beats Saxx when it comes to making boxer shorts for guys. Super soft and with a loose fit, they’re excellent everyday underwear for guys who like their drawers a little roomier.

What sets the Saxx Ultra Free Agent boxers apart from their competitors is Ballpark Support: A pouch that helps to reduce friction and keep your package in place with breathable mesh panels.

Flat seams and being machine washable just add to the charm and comfort. Perfect for moderate activity, like a stroll through the park.

Our Favorite Men’s Sexy Underwear

Mack Weldon 18-Hour Jersey Brief

Mack Weldon 18-Hour Jersey Brief

Been working out lately? Wanna show off the goods? You’ll definitely want to check out these low-rise briefs from Mack Weldon.

With a cotton, modal, and spandex blend, you’ll be as comfortable as you are attractive. The combination of three materials gives the best in durability, stretch, and coziness.

They’re available in almost 30 colors, meaning that you can mix and match them with any outfit – up to and including your birthday suit.

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Best Silk Underwear for Men

Man wearing a Tani silk Boxers

Tani 100% Silk Boxers

When you’re ready to invest in the highest quality luxury underwear, silk should be your go-to choice.

Tani has produced an amazingly comfortable set of boxers from pure mulberry silk, making it the ultimate in men’s leisurewear.

Once you try wearing this Tani underwear to bed even once, you’ll never want to go back to standard cotton briefs.

Best Leggings for Men

Photo of black Under Armour HeatGear 2.0 Leggings

Under Armour HeatGear 2.0 Leggings

Guys, leggings are not just for ladies in yoga classes. If you’ve never worn leggings during an intense run, ride, or sparring session, you’re missing out!

With a super breathable fabric, 4-way stretch, moisture wicking tech, and anti-odor treatment, these leggings from Under Armour just might become your favorite bottoms for the gym.

Comfortable and versatile, Under Armour’s HeatGear provides just enough compression for sporting activities, but not so much as to chafe or rub. Highly recommended to include as a part of your activewear wardrobe.

How to Choose the Right Underwear for You

While most guys know that a quality pair of jeans, basic t-shirt, and well-fitting boots are essential to your wardrobe, a great pair of underwear is often overlooked. For any man that’s taken an interest in what’s under their pants though, it’s quickly obvious that stylish, comfortable underwear with an attractive cut can make or break an outfit.

Finding the perfect men’s underwear for your style and budget can be a real challenge, though. Here are a few tips to keep in mind while searching for your ideal undergarments:

Find Your Favorite Style

If you’ve only ever worn one type of underwear – maybe even the dreaded tighty whities – you’ll have to start your journey by branching out into other cuts and fits.

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Basically, men’s underwear style comes down to three things:

  1. Leg length. Usually, guys prefer longer underwear for athletic activities because they help to prevent chafing.
  2. Hip rise. Men’s underwear can be fitted to be worn closer to your natural waist (at the belly button), or around the hips. Skinnier guys often prefer low rise, while more muscular fellas go for high rise.
  3. Roominess. Briefs and boxer briefs tend to keep everything snug, which is more suitable for moderate to vigorous activity. Boxers have more of a free, airy style that some men swear by for relaxed, lounging days.

Use these three criteria as a guide to point you in the right direction, but don’t be surprised if you find a place for all sorts of underwear in your wardrobe.

Try Out Different Materials

One of the biggest difficulties of shopping online for men’s underwear is not knowing how the fabric will feel. While a lot of what makes the best fabric for any style of underwear comes down to personal preference, we’re big advocates of choosing the right material for the right activity.

Cotton underwear is the most common type available but is known to lose its shape over time. While it’s an affordable choice that is easy to care for and breathable, just know that you’ll have to buy new pairs fairly regularly to keep them at maximum comfort levels. Choose cotton if you just need something to get you through the workweek, or as travel underwear that you won’t feel guilty losing.

Modal is the hottest newcomer to the men’s underwear scene, a product of the beech tree that is widely regarded as the most comfortable thing to have ever grace our junk.

Many of the new cult classic brands of men’s underwear incorporate modal’s moisture-wicking and shrink-resistant qualities. Look for modal fabric if you want the Rolls Royce experience for the boys downstairs.

Synthetics are most commonly found in underwear designed specifically for the gym or other high-intensity activities. They’ll often have odor-repelling, moisture-wicking, and extremely stretchy qualities that make them perfect for all sorts of running and jumping around. If you’re looking for the ideal underwear to up your fitness game and prevent swamp ass, synthetics are definitely the way to go.

A well-stocked underwear drawer will likely have pairs with each of these fabrics or a blend of them, so you can optimize your choices for whatever sort of day you might have.


No matter what type of underwear you’ve been sporting branching out and searching for your perfect fit is never a bad thing. Investing in comfortable underwear for everything life might throw at you can be a huge confidence booster.

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