Even the most style-conscious man can be guilty of phoning in his underwear game. After all, if you're investing top-dollar in great suits, great shoes, great outerwear, great grooming agents, why not save a little extra dough in the underwear department? I mean, it's not like anyone will notice—right?
Actually, wrong.
Wearing the perfect pair of upscale skivvies will indeed make you more comfortable, boost your confidence and sex appeal, and even help your clothes fit better. So before you decide to reorder another batch of the same crummy boxers you've always worn, peruse these wonderful pairs right here—all of which will ensure that you walk through life just a little bit taller. And if you're not sure which type works best for your body type, don't sweat it—whether you're tall, short, rangy, stocky, or heavy—we've got the perfect guide to choosing which type of underwear is best for you.
1 | Sleepy Jones Serra Boxer Brief
$22; Buy now on Amazon
Looking for seriously cool underwear with an under-the-radar hipster vibe? Check out Sleepy Jones ASAP.
2 | Mack Weldon Knit Boxers
$28; Buy now at mackweldon.com
These combine the silhouette of boxer shorts with the feel of boxer briefs, making them the best of both worlds.
3 | Sunspel Men's Printed Cotton Boxer Shorts in Liberty Print Blue
$70; Buy now at sunspel.com
Sunspel has been making men's underwear since 1860. We're pretty sure they know what they're doing.
4 | Brooks Brothers Supima Cotton Boxer Briefs
$19.50; Buy now at brooksbrothers.com
The reasoning behind this pick is pretty simple: Supima cotton is ultra soft. You simply won't find anything more comfortable.
5 | Lululemon Game On Boxer Brief
$24; Buy now at lululemon.com
Hailed as the holy grail of workout underwear, these Lululemon boxers won't let you down. Equipped with six colors options, flat seams that prevent chafing, and cooling technology, you'll probably never want to take them off. And for more good workout items, here is Running Coach Knox Robinson's Essential Running Gear.
6 | Uniqlo AIRism Boxer Briefs
$9.90; Buy now at uniqlo
Like the feeling of going commando? Then these are for you. Uniqlo created their AIRism technology to feel totally weightless, so it's almost like you're wearing nothing at all.
7 | Happy Socks Lucky Button Boxer Brief
$20; Buy now at happysocks.com
If you're in search of novelty styles, it's safe to say that Happy Socks has got you covered. Plus, if you're going to get lucky, chances are it's going to happen in these.
8 | Pair of Thieves Witness Stand Superfit Long Boxer Brief
$20; Buy now at pairofthieves.com
Pair of Thieves says their specially-made underwear fabric feels just like a basketball jersey in texture and is form-fitting yet breathable, making their styles ideal for the active guy.
9 | Emma Willis Two-Tone Slub Linen Boxer Shorts
$100; Buy now at mrporter.com
Made from the same material as premium shirting, these boxers both fancy and functional.
10 | Sunspel Men's Superfine Cotton Briefs
$45; Buy now at sunspel.com
Briefs don't have to be plain to look good—these striped ones from Sunspel are proof. Also, here are 15 Items Every Man Should Have in His Closet.
11 | Dolce & Gabbana Polka-Dot Print Cotton-Poplin Boxer Shorts
$235; Buy now at matchesfashion.com
Feel like treating yourself? Snag these Italian-made and ultra-luxe boxer shorts.
12 | Stance Wholester Cartridge
$36; Buy now on Amazon
Created with workouts in mind, these boxer briefs are made from one single piece of microfiber fabric that's breathable yet secure. They'll keep everything in place no matter what you're up to, and provide much-needed ventilation when things start to heat up.
13 | Calvin Klein CK Graphic Trunks
$38; Buy now on Amazon
Calvin Klein underwear is a classic for a reason. Providing the ultimate in comfort and style, you can't go wrong with these.
14 | ExOfficio Sol Cool Boxer Brief
$38; Buy now on Amazon
Consistently rated as one of the top underwear styles for men, these boxer briefs have built-in cooling technology that makes them ideal for pretty much any situation. They're also quick drying so you don't have to worry about feeling damp post-sweat session.
15 | Paul Smith Cotton Jersey Boxer Briefs
$45; Buy now at mrporter.com
A bright twist on basic white trunks, this funky pair shows a bit of personality.
16 | Saxx Strike Performance Long Leg
$49.95; Buy now on Amazon
Another great option for exercise, this longer style employs strategic panels and seams to give your key muscle groups some extra support, whether you're logging miles or hitting the squat rack.
17 | MeUndies Trunk
$20; Buy now at meundies.com
Trunks like these are an ideal everyday choice for guys with more muscular silhouettes as well as those who don't love to feel constricted by too much fabric.
18 | Thom Browne Printed Cotton Boxer Shorts
$125; Buy now at mrporter.com
Need something seriously stylish for a special occasion? These will do the trick.
19 | Zimmerli Sea Island Cotton Boxer Briefs
$130; Buy now on Amazon
These high quality cotton boxer briefs feature a super comfy waistband that won't dig in. By all accounts, you won't even know you're wearing them.
20 | Boss Hugo Boss Mini BM Microfiber Brief
$32; Buy now on Amazon
Microfiber is one of those fabrics that you just can't go wrong with. It's crazy soft and not too heavy or tight.
21 | A.P.C. Calceon Cabourg Trunk
$29; Buy now at endclothing.com
The French really know how to do the classics right, as evidenced by these basically perfect white boxers.
22 | Under Armour Original Series Boxerjock 2-Pack
$35; Buy now on Amazon
Another favorite according to online reviews, Under Armour sometimes can't even keep these guys in stock because they're so comfortable and work well under both gym clothes and casual wear.
23 | Hamilton and Hare Riviera Blue Boxer Shorts
$33.29; Buy now at hamiltonandhare.com
The ruched elastic waistband might look a little strange, but don't knock it until you've tried it. Having a stretchy back like this allows for a more snug, custom fit, meaning you don't have to worry about your boxers budging, no matter how active you are.
24 | Tommy Hilfiger Boxer Brief
$24; Buy now on Amazon
25 | Sleepy Jones Judd Brief
$18; Buy now on Amazon
Briefs like these are a great choice for when you're wearing tighter pants or shorts and don't want to add any extra leg bulk.
26 | Hanro Striped Mercerised Cotton Jersey Boxer Briefs
$50; Buy now at mrporter.com
Hanro products are built to last, so these are totally worth the investment. You can expect these boxer briefs to stay in mint condition after dozens and dozens of washes.
27 | Gap Stripe Block Boxers
$14.95; Buy now at gap.com
Gap has been a go-to destination for boxers for decades, and you know what they say: If it ain't broke, don't fix it.
28 | Calvin Klein Knit Slim Fit Boxers
$18; Buy now on Amazon
If you're one of those guys who wants to wear the same pair every day (less to think about when you're getting dressed, right?), we'd suggest these Calvin Klein classics. And hey, if they're good enough for Justin Bieber, they're probably good enough for you.
29 | Tommy John Cool Cotton Brief
$27; Buy now at tommyjohn.com
Briefs are one of the most practical underwear styles out there, but remember: ones that aren't plain white tend to be sexier.
30 | Mack Weldon Silver Trunks
$28; Buy now at mackweldon.com
There are actually tiny antimicrobial silver fibers woven into these guys, meaning you don't have to worry about staying fresh and clean when you're at the gym or on a really hot day.
31 | Derek Rose Gingham Cotton Boxer Shorts
$50; Buy now at mrporter.com
Derek Rose is famous for creating luxury pajamas and underwear for Old-Hollywood celebs, royalty, and billionaires. If you only want to wear best of the best, this brand is your best bet.
32 | Saxx Vibe Boxer Modern Fit
$31.95; Buy now on Amazon
There's a special place in every man's underwear wardrobe for a cheeky novelty print.
33 | Schiesser Karl-Heinz Boxer Short
$45; Buy now at endclothing.com
These 100 percent cotton boxer shorts are made with the closest attention to detail and quality. Even though they're soft, they're also super supportive.
34 | J. Crew Knit Boxer Briefs
$22; Buy now at jcrew.com
Though it's a small detail, the thin blue stripe at the top of these boxer briefs adds the cool vibe they need.
35 | Brooks Brothers Traditional Fit Large Overcheck Boxers
$25; Buy now at brooksbrothers.com
These are a little loud, but who says you can't have fun with your underwear every now and then?
36 | Uniqlo Supima Cotton Dots Boxer Briefs
$5.90; Buy now at uniqlo.com
Looking for a steal? Clocking in at under six bucks, you'd never know these comfy boxer briefs were such a bargain.
37 | Pair of Thieves Objection Super Soft Boxer Briefs
$20; Buy now at pairofthieves.com
There's something to be said for having a plain white pair of boxer briefs in your arsenal, and it doesn't hurt if they're super soft, too.
38 | Related Garments The Polka
$35; Buy now on Amazon
Related Garments' concept means you get a pair of dress socks and no-show socks along with every pair of underwear you buy, that way you're totally coordinated. Smart, right?
39 | Tommy John Second Skin Square Cut
$32; Buy now at tommyjohn.com
The super-short inseam on these allows for better range of movement for guys who just don't want to go for briefs.
40 | Hamilton and Hare Rio Red Trunks
$26.80; Buy now at hamiltonandhare.com
These lower-waisted trunks were designed to avoid that whole riding up on your thighs thing that this cut tends to do.
41 | My Pakage Heather Polka Dot Boxer Brief
$30; Buy now at mypakage.com
These are a great everyday option since they're lightweight and won't show under pants.
42 | 2[X]IST Stretch 3 Pack Boxer Brief
$tk; Buy now on Amazon
When you find a style you love, go for a multi-pack to get more bang for your buck.
43 | Emporio Armani Stretch Cotton Mega Logo Trunk
$35; Buy now on Amazon
Flyless underwear doesn't work for everyone, but it has its advantages: a smoother profile, comfort, and better aesthetics.
44 | J.Crew Popsicle Print Boxers
$18; Buy now at jcrew.com
Not really a winter person? Grab these while you're waiting for the weather to warm up.
45 | Happy Socks 3-Pack Contrast Trunk
$42; Buy now at happysocks.com
The pop of color on these trunks adds a little edge to a timeless style.
46 | The White Briefs Camouflage Print Briefs
$41; Buy now at matchesfashion.com
Camo is totally trending at the moment. If you're not ready to totally commit to the trend, try it out on your underwear. And here are some more Cool and Classy Ways to Wear Camo.
47 | Boss Hugo Boss Trunk Stripe Stretch Cotton Boxer Briefs
$34; Buy now on Amazon
If you're looking for some patterned underwear but are not sure where to start, stripes are always a safe bet; they add an interesting touch without going overboard.
48 | Stance Nightridge Butter Blend Boxer
$32; Buy now on Amazon
Made from Stance's signature Butter Blend fabric (which is supposed to soothe your skin), these boxers are awesome for sleeping since they're so crazy soft.
49 | ExOfficio Give-N-Go Sport Mesh 3" Boxer Brief
$28; Buy now on Amazon
Guys usually opt for cuts with longer legs for working out, but these short boxer briefs are breathable and supportive, too. They're also antimicrobial, which helps you stay odor-free.
50 | MeUndies Boxer
$20; Buy now at meundies.com
For those who love boxers but want to avoid butt-bunching, this style (which comes in every color imaginable) will be the new go-to. Now, check out The 20 Definitive Style Rules for Men Over 40.
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