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- If you feel like your outfit reads sloppy, try a loose full tuck or half tuck before anything else.
- Relaxed fit isn’t a bigger size. It’s a cut with more room in specific places, so buy your true size.
- Proportion is the most important thing to get right. When one half is loose, keep the other half contained.
- Fabric is essential. Linen, washed cotton and lightweight wool drape well (while a stiff polyester blend just looks like a big shirt).
Say “relaxed fit” and plenty of men will picture a baggy jumper, a shapeless linen shirt, cargo shorts that land somewhere between the knee and the ankle, and the general image of a man who doesn’t know how to dress well.
However, there’s a big difference between dressing for comfort and without intent, and dressing with deliberate looseness that borrows from ’90s Armani, Japanese workwear, and European men who look amazing at 11am on a Tuesday while sipping espresso on the sidewalk.
If you want to adopt the coolest menswear trend that came out of Pitti Uomo this year and which we’ll no doubt be seeing carried into the rest of 2026 and beyond, this guide is for you. Here’s how to nail the relaxed fit look without looking like you’re drowning in fabric.
Read more: The 9 Biggest Men’s Style Trends to Watch
The Basics of a Relaxed Fit
If you take anything away from this guide, let it be this: a relaxed fit isn’t just a bigger size. It’s a cut designed with more room in specific places, the seat and thighs on trousers, the chest and shoulders on shirts and jackets, all while keeping its proportion.
“One of the biggest mistakes I see is guys thinking that relaxed or loose fit simply means wearing clothes that don’t fit you. It doesn’t. There’s a big difference,” Personal Stylist and Image Consultant Christina Robért explains to Man of Many. “We don’t mean the shoulders don’t fit, the sleeves are too long, or the clothes look like you’ve borrowed your late uncle’s wardrobe. A relaxed fit is designed that way. It still needs to fit your body properly.”
You’ll also often see “oversized” used as a synonym for relaxed, but there’s a difference. Oversized means cut larger across the board, a boxy tee that drops past the hip, a jacket with a shoulder seam halfway down your arm. Relaxed is more proportional, meaning it’s generous where it counts and doesn’t ditch the overall structure of the garment.
Both oversized and relaxed fits are incredibly on-trend right now, but you need to know which one you’re wearing if you want to avoid the sloppy “I don’t know what I’m doing” look. Robért explains that oftentimes, oversized fashion requires a level of styling most men don’t have access to, which makes getting it right a lot more challenging.
“Take someone like Justin Bieber,” she says. “He can get away with a deliberately oversized look because it’s been curated to within an inch of its life by personal stylists and designers. That’s very different from buying a few oversized pieces and hoping they all work together.”
As such, most men should stick to relaxed, proportional cuts instead (especially when first trying this trend).
Why Proportion Is Important In A Relaxed Fit
There’s one thing that separates the men who wear relaxed fit well from the men who just look sloppy, and it’s proportion. The idea is simple: when one part of your outfit is loose, another part needs to stay contained.
For example, a billowy linen shirt with equally billowy trousers and an oversized jacket looks totally formless. The same shirt with straight-leg trousers and loafers looks well-thought-out. Another way of looking at proportion is balance. Your outfit has a top half and a bottom half, and the eye needs something to hold onto. Give it that anchor, and everything else can breathe.
“Loose up top, tapered down low, or vice versa,” Australian content creator and fashion personality Dirk Fourie told Man of Many.
“If your top half is generous, your bottom half needs to taper in, even slightly. If you’re wearing wide-leg trousers, keep what’s on top closer to the body. One loose element, one fitted element. The moment both halves are billowing, you lose the silhouette entirely and start giving snowman.”
| Top Half | Bottom Half | The Result |
| Oversized boxy tee | Straight-leg or tapered trouser | Clean, modern, purposeful |
| Relaxed linen shirt (untucked) | Wide-leg pleated trouser | Elevated, fluid, 90s Armani |
| Fitted or cropped shirt | Wide-leg or relaxed trousers (high-waisted) | Balanced, sharp, easy to wear |
| Dropped-shoulder blazer | Straight-leg jean or chino | Smart casual with style |
| Oversized jacket | Slim or tapered trouser | Structured at the bottom, relaxed at the top |
This isn’t a rulebook to follow per se – simply think of it as a starting point. Once you understand why these pairings work, you can start to push them.
1/25 Essential Relaxed Fit Pieces To Add to Your Wardrobe
1. The Pleated Trouser
Nothing says you understand relaxed fit like a good pleated trouser. The pleat isn’t a relic from your grandfather’s wardrobe but a design detail that adds room through the seat and thighs while letting the leg fall cleanly. Worn with a tucked shirt or a fitted knit, a forward-pleated trouser in a mid-weight fabric (wool, cotton twill or linen) is one of the most versatile things you can add to your capsule wardrobe.
The key is the break, or where the hem meets the shoe. You want to try to aim for a clean, single break at most. Anything pooling on the floor is too long, but anything above the ankle is too short for the relaxed trend look.
1/2The Linen or Cotton Overshirt
The overshirt or “shacket,” worn open over a tee or buttoned up, is the easiest way into relaxed dressing. According to Robért, it’s the ultimate anchor piece for the trend. “A shacket adds structure without making the outfit feel too formal,” she notes. “It gives the outfit shape while still keeping that relaxed feel.”
If you are very tall and lean, too much loose fabric can look like the clothes are wearing you. The trick is using the weight of a heavy shacket or an unstructured blazer to build necessary structure back into the outfit.
The rule: buy your true size. An overshirt is already cut loose, so there’s no need to size up.
1/2The Unstructured Blazer
The structured, padded blazer has had its time, but it’s time to retire this piece from your wardrobe. In its place is the unstructured blazer featuring no shoulder padding, with little to no lining, a soft lapel, and a fluid shape. In linen for summer or a lightweight wool when it’s cooler, worn over a plain tee and relaxed trousers, it’s about as easy as good style gets.
Specifically, you should be looking for the dropped shoulder. When the seam sits just off the natural shoulder, a centimetre or two lower, not halfway down your arm, you get that easy, slightly louche quality that defines modern tailoring right now.
1/2The Relaxed-Fit Jean
The skinny jeans are done (thank goodness). What’s replaced it sits between straight and wide: the straight-leg, the relaxed taper, the wide-leg and the barrel fit. For most men, a mid-rise straight or relaxed-taper in rigid denim is the most flattering and versatile pick. It gives you room in the thigh and seat while keeping the lower leg clean enough for anything from loafers to leather sneakers. The wash is also important to get right: a mid-wash in a rigid fabric looks sharper than a heavily distressed or faded pair.
Read more: The Only Men’s Jeans Guide You’ll Ever Need
Slim, Low-Profile Footwear
This is where a lot of guys undo their good work. Relaxed, wide-leg or oversized clothing doesn’t pair with chunky, bulky footwear. A wide trouser with a chunky sneaker sits bottom-heavy and are the fastest way to have your fit read as sloppy. The dad sneaker, the thick-soled, heavily branded, maximalist trainer, is on the way out.
What works instead is a slim, low-profile leather or suede sneaker, classic loafers (suede in tobacco or tan is strong right now), leather sandals, or a clean Chelsea or chukka boot. Footwear should be the full stop at the end of the outfit, not an afterthought.
“The right shoe saves the whole look,” said Fourie.
“Swap the sneaker for a clean leather shoe (a loafer, a derby, something with a defined edge) and suddenly the whole outfit looks styled. Think of your footwear as the full stop at the end of a sentence. Without it, the look just trails off.”
1/23 Tips to Help You Nail the Relaxed Fit
1. The Tuck, the Roll, and the Half-Tuck
One of the most underused moves in relaxed dressing is the tuck (something women have been rocking for eons). Tucking a relaxed or oversized shirt adds structure, marks the waist (even loosely), and makes the whole outfit look proportionate. A full tuck into a pleated trouser is clean and cool. A half-tuck, front loosely tucked and the back left free, is more casual but still looks great. The sleeve roll does similar work, for example, rolling an overshirt or relaxed button-up to just below the elbow.
Rule of thumb: if an outfit reads sloppy, try a tuck before anything else. It costs nothing and solves most problems.
2. Choose the Right Fabric
Why a relaxed fit works on some men and not others often comes down to the fabric. A relaxed shape in a good fabric like linen, washed cotton, lightweight wool, silk-cotton blends, and drapes well. The same shape in a cheap, stiff polyester blend just looks like a big shirt, which is exactly what you want to avoid.
Linen is the obvious summer pick. It wrinkles, but it wrinkles in a cool, chic, lived-in way. Washed cotton behaves similarly. And then when it cools down, a lightweight merino or brushed cotton flannel in a relaxed cut is about as comfortable and good-looking as it gets.
3. Mix it Up with Colour
Relaxed fit and neutrals go together, but you’re not stuck with beige and navy. Menswear is fairly generous with colour right now, pastels, 70s earth tones and muted botanicals are having their moment in men’s fashion, and we love to see it.
The trick is to let the colour do the talking when the fit is loose, rather than running a statement colour and a statement silhouette at once.
A simple guide: if the trousers are relaxed and wide in a bold colour or pattern, keep the top half neutral. If the top half is the star of the outfit (like a printed overshirt or a textured knit), then keep the bottom clean. Choose one focal point per outfit.
5 Mistakes That Make Relaxed Look Sloppy
1. Sizing up just because
Buying a size up isn’t the same as buying a relaxed fit. If the shoulders are sliding off your arms and the chest is billowing everywhere, that’s not relaxed. It’s just a fit that doesn’t fit.
2. Too much volume everywhere at once
An oversized jacket, an oversized shirt and wide-leg trousers all at once, with nothing to counterbalance, is exactly what you want to avoid. Pick one or two relaxed pieces and anchor the rest.
As Fourie warns: “The biggest error I see is treating ‘relaxed’ as a blanket instruction, like baggy shirt, baggy trousers, baggy jacket, the whole outfit billowing around you like a sail. You need at least one element of structure nearby. Loose on loose on loose just tells people you gave up somewhere around 2019 and never looked back.”
3. Ignoring the hem
Hems that pool on the floor, shirt hems that hit mid-thigh, jacket sleeves that swallow your hands – these are the details that tip relaxed into sloppy. Get things hemmed. Finding a good tailor is the best style upgrade you can make.
4. Cheap fabric in a relaxed cut
As above, fabric does a lot of the heavy lifting when it comes to relaxed fits. If it doesn’t drape well, then the shape won’t either.
5. The wrong shoes
Chunky sneakers with wide-leg trousers. Bulky boots with a fluid, oversized outfit. Both throw off the balance and undo everything else. Keep footwear clean and slim.
Quick-Reference: The Relaxed Fit Formula
| Occasion | Top | Bottom | Footwear |
| Weekend casual | Oversized tee or boxy linen shirt | Straight-leg or relaxed-taper jean | Slim leather sneaker or loafer |
| Smart casual | Fitted knit or plain tee | Wide-leg pleated trouser | Suede loafer or clean Chelsea boot |
| Business casual | Unstructured blazer over a plain tee | Relaxed chino or pleated wool trouser | Leather loafer or slim Oxford |
| Summer event | Relaxed linen shirt (tucked) | Wide-leg linen trouser | Leather sandal or suede loafer |
| Evening out | Dropped-shoulder blazer over a fitted tee | Straight-leg dark jean or tailored trouser | Clean leather sneaker or loafer |
Our Final Verdict
The men nailing the relaxed fit without veering into sloppy territory aren’t doing anything too complicated. They buy good fabric, they understand and play with proportion, they don’t size up for no reason, and they pair it with the right shoes.
However, Robért has one final piece of advice: “Don’t wear a trend just because everyone else is,” she advises. “Wear it because it feels like you. Relaxed dressing isn’t about wearing bigger clothes. It’s about getting the proportions right for your body and wearing them with confidence.”
If you do want to start playing with a relaxed fit, you don’t need to rebuild your wardrobe overnight. Start with one piece like a pleated trouser or an unstructured blazer, and let it work with what you’ve already got. Once you try a few different looks and start to really understand proportions, the rest follows.
Relaxed Fit FAQs
Oversized is cut larger across the board (like a boxy tee that drops past the hip or a shoulder seam sitting halfway down your arm). Relaxed is proportional (generous where it counts and doesn’t abandon the structure).
It actually tends to suit them better than a slim fit does. When you’ve got broad shoulders, a bigger chest, or a bit around the middle, a slim cut often fights what you’ve naturally got going on. Like we’ve learnt, the trick is proportion, not volume, so keep one half of the outfit contained and let the other breathe.
Yes but with two key adjustments. Keep the hems clean so nothing pools at the ankle or swallows your hands, and avoid going relaxed top and bottom at once. A relaxed trouser with a fitted knit, or a relaxed shirt with a straight-leg trouser, is your best bet.
Slim, low-profile shoes. For example, leather or suede sneakers, loafers, leather sandals, or a clean Chelsea boot.
Nothing in fashion is eternal, so it’s entirely possible we’ll see a returned rise in the slim fit sooner or later. However, even if the relaxed fit trend softens, the core pieces (a good pleated trouser, an unstructured blazer, a relaxed linen shirt) are wardrobe staples that outlast any single season.
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