Naughty Boy · Buying Guide

The Complete Guide to Buying Men’s Underwear (2026)

Sexy mens underwear is underwear built to be seen — briefs, jocks, trunks and thongs cut to show off what you’ve got. To choose well, pick the cut for the occasion, get the fit snug-not-tight, and buy fabric you’ll actually enjoy wearing. New to it? Start with a trunk; feeling brave? Go the jock.

8 min read Updated 3 July 2026
Confidence you can wear

The right pair changes how you carry yourself — a sharp cut and a proper pouch do more for your silhouette than an hour in the gym.

Built for the reveal

Date night, pride weekend, a cheeky photo — statement underwear is the outfit under the outfit, and it’s the part that gets remembered.

A cut for every mood

From everyday-wearable trunks to barely-there thongs, the range runs from subtle to shameless — you choose the dial setting.

In a hurry?

Top pick Prowler Open Back Brief — the statement brief that owns the room, front and back.
Best for beginners Cut4Men Athletic Trunk — a sporty, flattering cut you can wear every day.
Best value Envy Magic Unicorn Bubble Butt Jock — maximum cheek for twenty bucks.

What Counts as Sexy Men’s Underwear?

Sexy men’s underwear is any pair designed to show off rather than just cover up — lower rises, sharper cuts, contoured pouches and fabrics like mesh, wetlook and lace that regular department-store jocks wouldn’t dare. Same job as your everyday pair, twice the intent.

The category runs from briefs and bikinis through jockstraps, open-back styles, trunks and thongs, from labels like Envy, Prowler, Cut4Men, Male Power and Andrew Christian. Some pairs are everyday-wearable with a wink; others are strictly for an audience. Have a look through the full mens underwear range to see how wide it goes.

Is It Time to Upgrade Your Underwear Drawer?

If every pair you own is grey, saggy and older than your phone — yes, it’s time. Good underwear is the cheapest upgrade a bloke can make to how he looks and feels undressed.

Blokes buy statement underwear for honest reasons. It photographs well. It makes date night land properly. A contoured pouch genuinely flatters, a low rise lengthens your torso, and a bold print says you don’t take yourself too seriously — which is its own kind of attractive.

Straight talk on the trade-offs: fine mesh and lace need gentler washing than cotton, thongs take a session or two to stop noticing, and a jock is a commitment to your rear being the headline. None of it is a dealbreaker — just know which dial setting you’re buying. Pairing it with a look? A costume takes the same energy further.

Types of Men’s Underwear: Which Cut Suits You?

Men’s underwear splits into four main cuts — briefs, jockstraps, trunks and thongs. The right one comes down to how much you want to show and how long you’ll be wearing it.

Briefs & bikinis

The classic, sharpened. A sexy brief sits low on the hip with a contoured pouch and high-cut legs; a bikini cut goes lower and briefer again. The Prowler Open Back Brief takes the idea further with a full pouch up front and nothing but straps behind — brief in name, jock in spirit.

Jockstraps & open-backs

The cut that made cheeky an art form: full support in the pouch, open air behind. Once locker-room gear, now the go-to for pride, parties and anyone whose best asset faces backwards. The Prowler Paw Open Back Jock is the flagship look, and the Envy Magic Unicorn Bubble Butt Jock proves it doesn’t have to be serious.

Trunks & boxer briefs

The most wearable cut in the category — a square-cut leg that flatters almost every build, which is why it’s our beginner pick. The Cut4Men Athletic Trunk is the sporty benchmark, and the Envy Snap Down Mesh Boxer Brief adds see-through fabric and snap-open sides for after dark.

Thongs & G-strings

Minimal fabric, maximum statement. A thong keeps the pouch and trades the back for a strap; a G-string barely keeps the pouch. Party tricks exist too — the Male Power Rip Off Thong tears away with one tug, which is exactly as fun as it sounds.

CutBest forCoverageConfidence levelPrice band
Briefs & bikinisEveryday with intentFront & back, low riseStarter$25–$58
Trunks & boxer briefsAll-day comfort that flattersFull, square-cut legStarter$24–$64
Jockstraps & open-backsParties, pride, the revealPouch only, open behindConfident$20–$58
Thongs & G-stringsMinimal lines, maximum statementPouch & a strapBold$8–$49

How to Choose Your First Pair of Statement Underwear

Choose your first pair on four points: the occasion, the fit, the fabric and the budget. Get those right and the confidence part takes care of itself.

Occasion first

Be honest about where it’s going. Every day under work clothes? Trunk or brief. Date night? A low-rise brief or mesh boxer brief hits the sweet spot between suggestive and try-hard. Festival, pride or a night that ends late? That’s jock and thong territory.

Fit & size

Snug, never tight. The waistband should sit flat without digging, the pouch should hold everything forward without squeezing, and leg openings shouldn’t leave marks. If it’s cutting in, it’s working against you — the sexiest fit is the one you forget you’re wearing.

Fabric & feel

Microfibre and cotton blends wear all day; mesh and wetlook are for showing off; lace is the plot twist nobody sees coming. Anything with stretch (elastane in the blend) will fit better and last longer than a rigid weave.

Budget

Solid statement pairs start around $20 on promotion and the premium European cuts top out near $64. Start with one or two pairs to find your cut, then build the drawer — nobody’s first thong should cost more than dinner.

You’re dressing for…Go forLook forTry
Every day, with a winkTrunk or boxer briefStretch microfibre, flat waistbandCut4Men Athletic Trunk
Date nightLow-rise brief or meshContoured pouch, sheer panelsEnvy Snap Down Mesh Boxer Brief
Pride, parties, festivalsJockstrap or open-backBold colour, wide comfy strapsProwler Paw Open Back Jock
The grand revealThong — or a rip-offSoft pouch, tear-away sidesMale Power Rip Off Thong

Fabrics, Comfort & Feel

Fabric decides whether a pair is a keeper or a drawer ornament. Microfibre is the workhorse — silky, breathable and stretchy; cotton blends are the everyday soft option; mesh and wetlook are pure show; lace is softer than it looks and bolder than it sounds.

Check the blend before you buy: a touch of elastane means the pouch keeps its shape wash after wash. Sheer fabrics are lighter and cooler than they appear — a mesh trunk in an Australian summer is honestly a practical choice that happens to look filthy.

Sizing between brands: there is no universal size chart in underwear — a Male Power S/M, an Envy M/L and a Cut4Men M are three different animals. Always check the individual product’s size chart against your waist measurement in centimetres, and when you land between sizes in a snug cut, go up. European labels like Cut4Men run slimmer than American ones like Male Power.

How to Wear It with Confidence

Wear it like it’s no big deal — that’s the entire trick. A jock worn casually beats a brief worn nervously, every time.

Practical pointers: wear a new pair around the house first so the reveal isn’t also the fitting; match the cut to your outfit so nothing peeks out at work; and build up the dial — trunk, then brief, then jock, then thong. By the thong, the confidence is already installed.

Care, Washing & Making It Last

Wash statement underwear cold and gentle, and never tumble-dry it — heat is what kills elastic, and elastic is what makes the pouch work.

  • Mesh, lace and wetlook go in a wash bag on a delicate cycle, or a quick hand wash.
  • Skip fabric softener on stretch fabrics — it coats the fibres and slackens the fit.
  • Line-dry in the shade; sun bleaches bold prints and cooks elastane.

Our Top 7 Men’s Underwear Picks for 2026

These are the seven pairs we rate most highly this year — ranked, in stock and priced in Australian dollars. Every pick is a real product on our shelves, chosen on cut, fabric quality and value.

1
Prowler Open Back Brief
SKU NBA-PR002-REDWHT-M
$58

The statement piece of the range. A structured pouch and sharp red-and-white styling up front, open straps behind — a brief that commits fully in both directions. Sizes S–XL and more colourways in the range.

Shop this pick
2
Cut4Men Athletic Trunk
SKU NBA-C4M06DOLM
$56.93

The beginner’s best friend. A sporty European square-cut trunk with a contoured pouch that flatters without shouting — the pair to start with if your drawer is currently all grey cotton.

Shop this pick
3
Prowler Paw Open Back Jock
SKU NBA-PR004-BLUEPAW-L
$58

The party flagship. Prowler’s signature paw print on a proper open-back jock with wide, comfortable straps — made for pride weekends and rooms where you intend to be noticed.

Shop this pick
4
Male Power Rip Off Thong
SKU NBA-PAK-810-SM-BLK
$45

The showman’s choice. A classic black thong with tear-away sides that come off in one tug — the single most theatrical item in this guide, and it knows it.

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5
Ashella Lingerie Mica Boxer Brief
SKU NBA-ASH023
$33

The everyday sleeper hit. A soft, sheer-panelled boxer brief that’s comfortable enough for all day and cheeky enough for the end of it — the quiet achiever of the range.

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6
Envy Snap Down Mesh Boxer Brief
SKU NBA-BLE106-LXL
$24

Date-night engineering. Fine black mesh with snap-down front closures — a boxer brief that looks restrained until it very suddenly isn’t. Outstanding value on promotion.

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7
Envy Magic Unicorn Bubble Butt Jock
SKU NBA-BLE310-LXL
$20

Best value in the category. A bold unicorn-print bubble-butt jock for twenty bucks — proof that statement underwear doesn’t need to take itself, or your wallet, seriously.

Shop this pick

Still weighing it up? Browse the full range of men’s underwear and filter by cut, brand and size.

Men’s Underwear FAQ

What style of mens underwear is most comfortable?

Trunks and boxer briefs are the most comfortable cut for most blokes — a square-cut leg, no ride-up and a supportive pouch you can wear all day. Start there, then experiment once you know your size.

What is the difference between a jockstrap and a thong?

A jockstrap supports the pouch with elastic straps that frame an open rear; a thong replaces the rear entirely with a single strap. Jocks read sporty and cheeky; thongs read minimal and bold — both leave the back row uncovered.

What size should I buy if I’m between sizes?

Go up a size in snug cuts like briefs, jocks and thongs — a slightly relaxed pouch beats a pinching waistband every time. Always check the specific product’s size chart, because sizing varies noticeably between brands.

Can you wear a jockstrap every day?

Yes — plenty of blokes do. A well-made jock is supportive, cool and invisible under trousers; the only adjustment is yours. If open-back all day feels like a leap, alternate with trunks and build up.

What fabric is best for statement underwear?

Stretch microfibre is the best all-rounder — silky, breathable and shape-holding. Save mesh, wetlook and lace for showing off, and make sure any pair has elastane in the blend so the fit survives the wash.

How do I wash mesh or lace underwear without wrecking it?

Cold, gentle cycle in a wash bag — or a quick hand wash — then line-dry in the shade. Never tumble-dry and skip fabric softener; heat and softener are what kill the stretch.

Does Naughty Boy ship underwear discreetly?

Yes — every order ships Australia-wide in plain, unmarked packaging with a discreet sender name. Nobody knows what’s in the parcel but you.

Why Trust Naughty Boy

Australian & here for you We’ve spent years helping Aussie blokes dress up, dress down and buy well, with local support that knows the range.
Real brands, real range Envy, Prowler, Cut4Men, Male Power, Andrew Christian — hundreds of styles, hand-picked and honestly described.
Discreet plain-packaging Every order ships in plain, unmarked packaging — your drawer upgrade is nobody’s business but yours.
Secure checkout Safe, encrypted payments and a support team based right here in Australia.

Not sure which cut is you?

Tell us the occasion and your size and we’ll point you to the right pair — discreet, no-judgement, straight-up advice.

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