AskMen Guy Gear Awards 2025 Best Clothes and Wearables

You’re a lot more than just the clothes you wear, it’s true. But what you’re wearing does tell other people about what kind of person you are. Wearing a perfectly tailored suit? You’re probably rich and fashionable. Wearing old and raggedy workout apparel? You’re probably a determined gym rat. Wearing exclusively products from the below list? Well, you’re probably cool as hell. That’s because, as we tested out items of clothing for these awards, we prioritized stuff that made us look and feel: cool, badass, and comfortable as hell. After months of trying stuff on and wearing it out (and washing it) we’ve come up with a list of 27 dope pieces of clothing that we think you’ll love too. And now, please check out the winning clothes and wearables from the 2025 AskMen Guy Gear Awards: Editor’s Note: Because it’s 2025 and AI slop is everywhere online, we wanted to let you know that generative AI and LLMs were not used in the production of the Guy Gear Awards. We were hands-on about it, and quotes directly from our testers are included throughout to give you a sense of how actual human guys feel about this stuff. Best Tops Best T-Shirt Alo Yoga Conquer Reform Crewneck Short Sleeve The T-shirt is the atom of American clothing, the simple building block of the wardrobe, the foundation upon which looks are built. Meaning, even if they’re inexpensive and not especially swagged out, a genuinely nice one can start your day off right. This model, from yoga-focused brand Alo, is a delight to wear — soft and breathable but in a way that feels well-constructed as opposed to flimsy.Check it out at AloYoga.com Best Crewneck Sweatshirt Sunspel Loopback Sweater Add a little bit of heft and a lot of sleeve to your T-shirt and you get the beautiful crewneck sweatshirt. A great one can span the distance between the gym locker and the romantic date night, and this might just be such a sweatshirt. It’s an upscale take on the form by British brand Sunspel that boasts all the little details that make a good sweatshirt great: loopback stitching, a V-stitch insert to keep that neck hole looking good, and rib cuffs for easy sleeve-rolling. Check it out at Sunspel.com Best Hoodie Ibex Mammoth Full Zip Hoodie Take a sweatshirt and give it a little dose of bad-assness and you get the hoodie. Cozy, warm and, crucially, with the ability to cover your head and your torso simultaneously, it’s like if a slanket had street cred. This one, from merino champions Ibex, is a serious hit. Our testers say: “I was really impressed with this hoodie. It's thick yet thermo-regulating and breathable due to the merino, which has the further benefit of still keeping you warm, even if it gets wet. It's soft, and feels luxurious.” Check it out at Ibex.com Best Heavy Jacket Overland Classic Sheepskin B-3 Bomber Jacket If it gets cold as hell where you live, you’d be crazy not to have a heavy jacket. The shearling lining on this sweeeet-looking bomber jacket from Overland, we’ll admit, is giving 5% Santa Claus outfit, but the remaining 95% is comprised of “tough guy jacket” and “model at an après-ski-themed outerwear photoshoot” so we can forgive it. Plus, it’s temperature-rated down to 1 degree Fahrenheit. Pretty cool stuff. Check it out at Overland.com Best Light Jacket On Court Jacket It’s a truth universally acknowledged that guys look good in jackets. And while the windbreaker might not be what people have in mind when they think of a guy in a cool jacket, the right windbreaker can change a person’s mind. This one, from On, is basically the total package. Our testers say: “I've been using this jacket as my daily wear these colder summer nights, and even through some light rain. It's the perfect windbreaker: lightweight, compact (rolls up super small), and effective against the weather. It doesn't feel like a sauna when you have it on either.” Check it out at On.com Best Trucker Jacket Wrangler Sherpa Lined Corduroy Trucker Jacket You don’t need to be a trucker to wear or own a trucker jacket. And thank God for that, because they’re basically a magical genie wish for looking 500% cooler instantaneously. This one from Wrangler blends serious comfort with dashing good looks, and for that, we salute it. Our testers say: “It's super cozy, and I was surprised by that, since I was expecting a jacket, but it feels like a sweater? But that means it's cozy like a sweater but looks mostly like a jacket, which is pretty sick. It's super cozy and I'm really looking forward to stealing it from my boyfriend in the fall months.” Check it out at Wrangler.com Best Chore Jacket Dickies Denim Chore Coat French-style chore coats, long associated with a more European aesthetic, are coming over to North America as of late and we’re here for it. We love the way they communicate a sophisticated, old-school masculinity, and this great one from Dickies is no exception. A strong option for guys who have a little urbane, stylish vibe but still work with their hands — or want to look like they do (we won’t tell). Check it out at Dickies.com Best Vest The North Face 1996 Retro Nuptse Vest Jackets are great and all, but not everyone lives in colder climes, and sometimes having freer arms is a real treat. Thankfully, the trusty vest exists. Though recent years have shifted vest vibes a little towards the “tech bro” category (OK, a lot towards it), a classic model like the 1996 Retro Nuptse from North Face still has a definite cachet. Plus it’s got a hidden hood in case stuff gets crazy (no hidden arms to turn it into a jacket, though). Check it out at TheNorthFace.com Best Bottoms Best Sweatpants Psycho Bunny Levy Essential Fleece Sweatpant Is there anything better than pulling on your cozy sweatpants once cooler weather comes around? They’re like the soup season of pants. The sweatpant is a simple concept, but like many simple concepts, lots of people get them all wrong. Not Psycho Bunny, though — the Levy is pretty close to the Platonic form of the ideal pair of sweatpants. Three pockets, drawstring, 100% cotton, no crazy graphics or visual nonsense. Thank you, Psycho Bunny. Check it out at PsychoBunny.com Best Cargo Pants Alpha Industries M-65 Pant Cargo pants are the Guy Gear Awards of pants. Tough, verging on badass, but also a bit silly. And you know what? We say, lean into it — the way Alpha Industries did with their sweet M-65 model. Our testers say: “As a cargo pant, these guys are almost perfect in fit, and, you know, they have a lot of super cool pockets, which is really what you want in a cargo pant. The fit and the silhouette are great, and they're comfy as hell. It has a ton of straps, but they do add to its cool factor in a weird way.” Check it out at AlphaIndustries.com Best Jeans DUER Tech Fleece Denim To be honest, this is the first time we’ve included jeans in the Guy Gear Awards. The Guy Gear ethos is all about comfort and function, and in our experience, jeans are rarely scoring high on both scales at once. They’re straightforward, relatively accessible pants that look good on most guys. But this pair from DUER, thanks to its injection of fleece interwoven into the denim, allows for great weather-proofing while remaining flexible for comfort. They cracked the code…Check it out at ShopDUER.com Best Shorts UNTUCKit Traveler Tech Shorts We really got a kick out of testing these out this summer. If you want a short that’ll look good at the backyard barbecue while still being comfortable enough to chill in before and afterward, you’ve found your match. They’re nice and stretchy without being weird about it, they’re water-repellent and dry easily in case you get a little wet at the BBQ via being thrown in the pool or simply spilling a drink on yourself. Not that that would ever happen to us.Check it out at UNTUCKit.com Best Active Shorts Gorewear Concurve 5-Inch 2-in-1 Shorts Not all shorts are great for getting active in, even if they’re great all-purpose shorts. Sometimes, you want ones purpose-built for getting sweaty and nasty in. We’re big fans of this entry from Gorewear, which turns a seeming shortcoming into an advantage. Our testers say: “Only one pocket? That’s it??? I can’t bring my phone and my keys and my wallet at the same time? OK, Gorewear Concurve. I’ll play your twisted game. They force you into a minimalist headspace that I really appreciated and that helped me stay in the moment when it came to my workouts.” Check it out at Gorewear.com Best Hybrid Shorts All Citizens Titan Shorts + Detachable Pocket Speaking of one powerful pocket… Ever wished you could take your shorts into a body of water without worrying about your valuables? Wish no longer, because All Citizens’ Titan Shorts can now be purchased along with a detachable waterproof pocket. What were we just saying about being thrown in the pool? If that’s a concern of yours, these may be for you… Just think how surprised all the other BBQ guests will be when your phone is completely bone dry. Check it out at AllCitizens.com Best Underwear BN3TH Pro Ultra Boxer Brief What were we saying earlier about your T-shirt being the foundation of an outfit? That was all wrong. Your underwear is the real foundation. Slap on a pair of something great — like the Pro Ultra from BN3TH — and your day’s already off to a good start. Our testers say: “Comfortable, durable, good-looking without being attention-grabbing. These boxer briefs are best-in-class. Makes me want to throw out all my other pairs.” Check it out at BN3TH.com Best Footwear Best Active Sneakers Saucony Endorphin Speed 5 Going for a run? Or at least a high-intensity jaunt of some kind? You’re going to want some sneakers on your feet. Right now we’re really digging the Endorphin Speed 5 from Saucony. Lightweight and comfortable, they’re just straight-up fun to run in, and the citron/lapis colorway is like a little jolt of energy just to look at. Check it out at Saucony.com Best Casual Sneakers Allbirds Tree Dasher 2 While active sneakers are an important part of any guy’s rotation, so, too, is the casual sneaker. Sometimes you want to just, you know, kick it. In that context, you can absolutely go back to your workout shoes, but it’s also nice to have a separate pair that puts a bit more emphasis on looks and comfort — like the Tree Dasher 2 from Allbirds. Our testers say: “I got to test a bunch of sneakers this summer and these are the ones I keep coming back to. Super comfortable, easy to put on, they’re breathable, they look nice but also fun but also cool. 10/10, no notes.” Check it out at Allbirds.com Best Rugged Shoes Merrell Wrapt Mid Waterproof We took one look at these and went, “Yep, that’s Guy Gear material.” Thankfully, the actual shoes lived up to our expectations, and then some. Putting these on legit feels like you’re in a superhero suit-up montage, and the Quantum Grip sole and the way it wraps around the edges means you can run, jump and boogie wherever and however you like with full confidence that you won’t lose your footing. Check it out at Merrell.com Best Water Shoes Salomon Techamphibian 5 Need to get your feet wet? Want to dip a toe in first? Some other “stepping into a body of water” metaphor? Consider wearing a pair of Salomon’s Techamphibian 5s while you do it. Our testers say: “I absolutely love love love these shoes! They are durable and comfortable; I wore them straight out of the box and I didn't end up with any blisters or anything; they handle walking over terrain and wet rocks very well! They also dry quickly in the sun and just look very cool.” Check it out at Salomon.com Best Everyday Boots Blundstone #2428 Lace Up Boots While Blundstone may be primarily known for their awesome Chelsea boots, this year, we wanted to show some love to the work they’ve put in on their lace-up models. The #2428 is a good, honest boot that won’t try anything funny on you. It’s comfortable, durable, and brings all the high quality of regular laceless Blundstones with all the micro-fit adjustments possible with laces. What’s not to like? Check it out at Blundstone.com Best Work Boots Wolverine Vantage BOA Sometimes, you just need some really damn heavy-duty boots. Whether you’re on the job or simply in clomping-around mode, boots designed for non-work purposes simply won’t cut it. If that’s your situation, get yourself a pair of the Vantage BOAs from Wolverine. They’re super comfortable, somehow look sleek and rugged at the same time, and the handy tie-box feature means you’re never bending over to re-tie your laces. Check it out at Wolverine.com Best Comfy Socks Kashwére Lounge Socks Dear God are these comfortable! Not really a lot to say here other than, wow, they’re so comfortable. It’s like wearing a cloud??? Why isn’t every pair of socks like this? They’re sooo comfortable. Check it out at Kashwere.com Best Sandals Teva Hydratrek Lots of guys feel like showing off their toes is still somewhat taboo, but strap on a pair of these bad boys, which won a Guy Gear Award last year as well, and you’ll be having a change of heart in short order. Our testers say: “I wore these sandals at every opportunity I had this summer and they're great! Super comfy — took them on light hikes, sandy and rocky beaches and I even went to some really muddy places while on vacation. They can handle water, clean easily and dry really quick!” Check it out at Teva.com Best Headwear Best Fashion Sunglasses Tom Ford Metal T-Inlay Round Sunglasses Sunglasses are kind of like the jacket of the face, in that guys can seriously wear the hell out of a pair and look kind of jaw-droppingly good doing it. This pair from Tom Ford has a slight aviator influence to them, but in a refined and elevated way that makes them even cooler than the standard model. Our testers say: “I've worn them almost every day since I got them. I love them, they get compliments, and they look and feel fashion-forward.” Check it out at HarryRosen.com Best Active Sunglasses Oakley Ellipse Sunnies are for more than just looking hot, though — they’re also a highly useful addition to your workout gear if you’re ever one of those people getting their sweat on in the great outdoors. While experts might argue these are beginning to horn into the next category somewhat, we really love them for their ability to handle on-court action (or pitch, or track, or… you get the idea). They’re sturdy, protective and, OK, also very cool-looking. Check it out at Oakley.com Best Cool Sunglasses Moncler LASZER 0ME8008 Some sunglasses are for straightforward fashion. Some are for looking cool while you work out or engage in extreme sports. And some sunglasses are just for looking undeniably wild. This is that third category. Our testers say: “These glasses are really cool. They look super sleek and sporty. The lens tint is amazing, it maintains a lightness while still making you feel like your eyes are protected. When I first got them, every single one of my friends wanted to try them on. They have an absolutely unique look that’s so cool.” Check it out at Moncler.com Best Hat New Era Three Looms Floral Cord Fitted Ahh, the trusty baseball cap. Where would we be without you? You cover bald spots, bed head and bad haircuts alike, promising each of us a day of looking normal when our domes feel anything but. Anyway, call us saps, but every year, New Era drops a new collection that has us do a little double take, and this year it’s this gorgeous floral-themed corduroy concoction co-created with Three Looms. Check it out at NewEraCap.com You Might Also Dig: Check Out All 73 of Our Winning Guy Gear Products Here21 Seriously Sweet Products to Transform Your Space Into the Ultimate Man Cave25 Awesome Pieces of EDC Kit to Make Sure You’re Ready for Anything Life Throws at You