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How to Choose the Right Men's Underwear for Any Occasion

Your underwear is a critical fashion choice. Frankly, if you don’t put the same thought into your skivvies that you do into every other piece of clothing, you’re doing yourself a serious disservice.

But you may have noticed that underwear options have exploded over the last few years. Trunks, briefs, boxer shorts, boxer briefs… which is right for you? And what underwear style should you pick when you’re gearing up for a workout / day at the office / chill evening at home, etc.? If you feel overwhelmed, we’ve got your back. This handy little guide will help you get savvy about your top drawer.

Know your measurements

Before you start shopping for underwear, take the time to measure your waist and hips accurately. This will help you find the perfect size for your body type. You can use a measuring tape, string, ruler, and underwear size chart to get the most accurate measurements possible.

Once you know your measurements, you can start exploring different styles of men's underwear. There are a variety of options to choose from, including boxers, briefs, trunks, and more. Each style has its unique benefits and drawbacks, so it's important to consider what will work best for your body and lifestyle.

Doing physical labor: Boxer briefs

If your job involves a lot of bending, lifting, and moving, you need sturdy undies with the right hip size and a wide leg opening that can keep up with all those movements and a little sweat. They should also be form-fitting to offer plenty of support. Tommy John’s Cool Cotton collection is durable enough to stay in one piece but designed to handle a lot more moisture than the cotton undies of yesteryear.

Doing office work: Trunks or briefs

But what if you’re working at a desk? You still need all the comfort you can get - but that means less material, and lighter material. When you’re sitting for extended periods, smaller skivvies - either trunks or classic briefs - will leave you comfy and airy. For the best material, check out our Second Skin briefs. They’re silky soft, and the breathability can keep you feeling cool even in stuffy work slacks.

Hitting the gym: Briefs or boxer briefs


When you’re planning on going full speed, there are two major factors you want to look for in your gym underwear: Support and sweat control. (It’s also crucial that you bring a fresh pair of mens underwear to put on after your post-workout shower.)

For support in men’s underwear, that means skipping the boxer shorts and choosing something with more support. Briefs or boxer briefs will keep you supported upfront and in the rear, as you move, climb, hop, or squat. For sweat control, check out the 360 Sport collection for sports underwear with fabric that can keep you dry, no matter how intense your perspiration gets.

Choose a style that will keep your booty from uncomfortable bouncing, and features an elastic waistband designed to keep the underwear in place no matter how intense your stretching is. For fabric, shop Tommy John’s, Air Collection - it’s a light, breathable underwear fabric that dries in a flash and is guaranteed not to show through your workout pants.


Skinny Jeans and other tight clothes: Briefs or Boxers

Nothing ruins the sleek look of your favorite pair of skinny jeans like a visible underwear line showing. Visible underwear line (aka VPL - visible panty line) is a hazard for men and women alike, as it can make you seem sloppy no matter how clean and put together your outfit is otherwise. So, how to choose underwear size for men? For men, form-fitting briefs in the right size will be perfectly invisible under skinny jeans or tight slacks. To find the right underwear size and measurement for you, view our underwear size chart

Tommy John’s Air Collection offers underwear that won’t show panty lines regardless of style or cut. No matter what you’re wearing, these skivvies stay perfectly hidden.

Lounging around: Boxers or classic briefs

When you’ve got nothing on your agenda but chilling, you should celebrate with the comfiest pair of underwear in your dresser. This is where boxers can shine brightest. There’s nothing like the breezy, open-ended nature of old-school boxer brief to keep comfy while you sprawl and laze the day away.

Both ladies’ and men’s briefs have gotten a bad rap for looking dated, but they’re actually a cozy choice for a lazy day. There’s less fabric on your legs so you have more freedom to stretch and move, and they do a great job of keeping everything in place. Tommy John has given an essential update to this classic underwear style for men and women, perfect for a quiet sunday.

Date night: Whatever makes you feel sexy

When you’re vibing with another person, there’s nothing more important than confidence. That might mean skivvies you feel comfortable being seen in. It might also mean stepping out of your comfort zone.

For a more classic and sophisticated look, you can go with briefs. This style offers a snug fit that can help show off your body, while the traditional design shows your confidence and style. If you want to add a little personality, choose a pair of comfortable underwear in a bold color or pattern.

On the other hand, if you're feeling more daring, consider boxer briefs. This underwear style combines a form-fitting cut that highlights your assets with a longer leg that provides additional coverage. For an extra touch of luxury, go for a pair made from a silky smooth fabric.

Regardless of your preference, remember that confidence is key. Put on something comfortable, take a deep breath, and let your best self shine through. With your charm and confidence, your date won't be able to resist you, and you'll have an unforgettable night.

No matter what underwear style you choose, don’t wear old, tattered undies! Even if you have no plans to disrobe, you deserve better.

The bottom line

When it comes to premium men's underwear, a stylish look is only part of the battle. Underwear should also fit like a dream and be cozy no matter what the occasion is. If you’re fighting to keep your underwear in place or dealing with itching and irritation at the seams, it’s time for an upgrade. Shop Tommy John’s collection today to find your perfect fit.