When we think of fun items to buy, underwear is not at the top of our list. Sure, it’s a necessity for most (more power to you if you choose to hang free), but like most necessities, it feels like a chore to buy. It’s the item that no one was ever excited to get in their Christmas stocking. During childhood, it was a purchase that was delegated to our parents and was the source of instant mortification if it was discussed in public. You may still be reeling from the time your mom held up a pair of underwear in front of you in the mall and asked whether you liked the color. Did you run into classmates at a department store while your parents were shopping for your underwear? You probably had to change schools.
Underwear can be your best friend or your biggest enemy. The difference between a pair of comfortable undies and a pair that causes an ill-timed wedgie can make or break a day. We haven’t read any studies to back this up, but we wouldn’t be surprised to learn that 80 per cent of all road rage incidents are caused by an ill-fitting pair of underwear.
Now that you’re an adult and buying your own underwear, it’s time to get the pair you really want. Thanks to the internet, you no longer have to endure browsing the underwear section in public. Everyone wears underwear and there’s no shame in the boxer brief game, but that still doesn’t mean you want to ask for assistance from a clerk when looking for the undies with the most support. It’s awkward.
Fun prints and colors are a great way to make buying underwear an enjoyable task, but at the end of the day, when looking for a product that covers your most sensitive area, it’s all about comfort. That’s why we’ve put together a list of the most comfortable boxer briefs on the market that you can browse from the comfort of your own home while wearing only your boxer briefs. Just make sure they’re comfortable.
1. UnderGents Men’s Boxer Brief Underwear
UnderGents Men’s Boxer Brief Underwear are made with 95 per cent modal, a type of rayon, and 5 per cent spandex, making a flexible boxer brief that will move with your body, not against it. Rejecting compression fit and instead using CloudSoft technology, UnderGents pride themselves on being ‘the most comfortable underwear you’ve ever worn.’ The mirco modal fabric is softer and cooler than traditional cotton and polyester and the CloudSoft technology is permeable, which keeps you and your underwear moisture-free, which means no unpleasant chafing or sweaty smell coming from down there. Our team loves the attention to detail found in UnderGents, including the flat stitching, no tag finish to eliminate chafing, a seamless seat to make any sitting position comfortable, and a contoured front pouch with added support.

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2. David Archy Ultra Soft Comfy Breathable Bamboo Rayon Trunks
David Archy Ultra Soft Comfy Breathable Bamboo Rayon Trunks have a huge following and we know why – they’re super comfortable! Made from 95 per cent Bamboo Rayon and 5 per cent Spandex, the boxer briefs have a lush, silk finish that makes them feel luxurious next to your skin. The bamboo makes the boxer briefs breathable, lightweight and quick drying, which makes these a great option to wear when working out or in hot climates. The 3D front pouch has added room for comfort and a one-piece clean cut bottom section means no unpleasant wedgies. Customers note that the underwear runs on the smaller side and has shorter legs than competitors, which is something to keep in mind when ordering your size.

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3. Hanes Ultimate Men’s Comfort Flex Fit
The Hanes Ultimate Men’s Comfort Flex Fit are a great option for anyone looking for an affordable and basic boxer brief that still packs in a lot of comfort. The boxer briefs are made with a blend of 57 per cent cotton, 38 per cent modal and 5 per cent spandex, which combined makes a boxer brief that wicks away moisture and helps keep you feeling cool and dry all day. Some customers find the waistband too bulky and tight and report that Hanes fit looser than competitors, which is important to know when considering personal preference.

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4. Separatec Men’s Micro Modal Separate Pouches Comfort Fit Boxer Briefs
Separatec Men’s Micro Modal Separate Pouches Comfort Fit Boxer Briefs are made with 92 per cent Micro Modal and 8 per cent Spandex, creating a comfortable and highly elastic boxer brief. If you often find that your boxer briefs leave you with discomfort in the front, these may be your new best friend. The Separatec have an additional crotch panel that improves comfort and reduces friction. It also has two separate pouches, with a front pouch that keeps you feeling fresh and a lower pouch that provides additional airflow and support. Separatec has a hidden hole that makes bathroom trips easy and discreet and the legs measure on the longer side at 6.5 inches, which is great for people who often have issues with their boxers riding up.

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