Best Underwear for Gay Men: Picks for Every Mood

Open your underwear drawer for a second. Go on. If every pair in there looks more or less the same, you are not alone, and you are also missing a trick.

Most guys find one style they tolerate, buy it in three colors, and never think about it again. That is a shame, because the pair you put on first thing sets the tone for the whole day. It is the one thing you wear that nobody sees and everybody feels, and the right pair can quietly change how you carry yourself from the moment you pull it on.

At Bill and Brandon, we have never believed in one perfect pair. We believe in the right pair for the mood you are in. So instead of crowning a single winner, here are our picks for every mood a gay man dresses for, from a lazy Tuesday to a night you have been looking forward to all week.

THE EVERYDAY WORKHORSE

Start with the pair you will reach for most. This is the underwear for work, for errands, for the days when nothing exciting is happening and you just want to feel good in your own skin.

For most men, that means a good brief. Briefs sit close, support everything properly, and disappear under whatever you are wearing with no ride-up and no fuss. Our Brandon Brief is the one to beat here, cut for a snug fit with a contoured pouch that keeps everything exactly where it should be. If you want a little more length down the leg, a boxer brief gives you the same support with extra coverage against your jeans.

People often ask what the most comfortable underwear for everyday wear actually is, and the answer usually comes down to fabric. This is where our Bamboo Boxer earns its keep. It is made from a bamboo blend that is soft, breathable and naturally anti-bacterial, with dual-pouch anatomy separation, which is a polite way of saying it keeps things comfortable and stops the dreaded stick-and-chafe on a warm day.

Everyday does not have to mean boring. It just means reliable. Get this layer right and the rest of your drawer gets to have more fun.

THE GYM AND SPORTY PICK

Ask most gay men what they wear to the gym and the jockstrap comes up fast, for very good reasons. It was built for sport in the first place, so it does the practical job brilliantly. The full pouch gives you support and protection where you need it, and the open back means air gets to move around instead of leaving you damp halfway through leg day.

There is a happy side effect too. Those elasticated back straps lift and frame the bum in a way that is very hard to ignore, which is exactly why the jockstrap has never stayed confined to the gym. Our jockstraps are made to handle a proper workout and turn heads in the locker room, and Bill's Jockstrap is a great place to start if you have never owned one.

If a full jock feels like a lot for the treadmill, a supportive brief in a breathable fabric will see you through most sessions. Save the jock for the days you want a bit of a strut on the way out.

THE BOLD, SHOW-IT-OFF MOOD

Some days you just feel it. You caught your reflection, the gym is finally paying off, and you want underwear that keeps up with the mood. This is thong and mesh territory.

A thong is the boldest, most minimal thing in the drawer, and it is a lot more comfortable than the nervous first-timer expects. It gives you a full front pouch, next to nothing at the back, and a clean line under anything tight. If you want the confidence with a fraction more coverage, a jock sits somewhere in between. Our jocks and thongs range covers the whole spectrum, so you can dial the boldness up or down to suit the day.

Then there is mesh. A sheer mesh brief or boxer gives you that barely there look while still technically covering you, and it feels as good as it looks. It is the easiest way to take an everyday style and make it a statement, and it works whether you are the only one who knows it is on or not.

THE BIG NIGHT

Now for the pair you save for a reason. When the night matters and you want to make an impression, this is where you reach past the everyday drawer entirely.

This is the moment our Beast and Bulge range comes into its own. It is our boldest, most body-defining line, cut for a snug, confident fit that makes you feel like the best version of yourself before you have even left the house. Pair a Beast Brief with the confidence it gives you and you are sorted.

If your big night is more about barely there than bulked up, a sheer thong or a mesh pair does the job just as well. The point is the same either way. This is underwear chosen to be seen, or at least felt, and it should make you grin a little when you put it on.

PRIDE AND PARTY

Some occasions are not about subtle at all. Pride, a circuit party, a festival, a big night out with the boys. These days call for color, and they call for a bit of noise.

Our Fluid and Fierce range is built exactly for this. It is our Pride and statement line, full of bold prints and celebratory pieces made to be shown off rather than hidden. Team a loud pair with your best rainbow socks and you have an outfit that says everything before you do.

Party underwear should feel like a celebration, because that is the whole point. When the occasion is joyful and loud, your underwear may as well be too.

FIND THE PAIR THAT MATCHES YOUR MOOD

So there is no single winner, and there was never going to be. The best underwear for a lazy Sunday is not the pair you save for a first date, and the pair you wear to deadlift is not the one you pull on for Pride. Once your drawer covers every mood, getting dressed stops being a compromise. You just reach for the pair that fits the day ahead.

If you are building that drawer from scratch, our range of the best underwear for gay men is the place to start, with a style for every mood on this list. For a deeper look at how the different cuts compare, our go-to guide to underwear styles for gay men breaks it all down.

We are a UK brand with daily dispatch, eco-friendly packaging and more than 500 reviews from guys who came back for the next pair, with most single styles at £22.99. Have a browse of the full range, check the FAQs if you are unsure on sizing, or get in touch and we will help you find your fit.