How To Wear Baggy Jeans: 19 Modern Looks For 2023
Modern and on trend, here's how to style wide-fit jeans without it looking like you've raided your dad's wardrobe.
They’re the stuff of Seinfeld episodes, Backstreet Boys videos and vintage ads for Calvin Klein and Tommy Hilfiger. And yes, they were a staple of nineties and early noughties men’s fashion, but baggy jeans couldn’t be more now.
Innately casual and urban, you’ll spot this style of denim in every cool city in the world right now: waiting in the queues by food trucks, loafing around craft brewery tap rooms, and definitely folded on the shelves of the best menswear shops in town.
How to wear baggy jeans has changed a little in the last 30 years. Making slouchy-fit denim right for the 21st century is about more than Tupac or Tony Hawk cosplay. You’re still channelling hip-hop and skatewear, emo and grunge but one of the ways men’s style has evolved is that it’s less tribal than it used to be.
You can take those references and wear them faithfully. You can also remix them in new ways or wear baggy jeans with pieces that Fred Durst wouldn’t have dreamed of (a good thing – no offence, Fred).
To give you a few things to think about, read on for tips and go-to outfit ideas for wide-fit jeans.
How to wear baggy jeans
How wide is baggy?
There’s baggy and then there are clown jeans, and it’s important to distinguish between the two. Baggy jeans can be wide through the thighs all the way to the hem, or they flare out at the bottom and pool around you feet – but in either case they should still fit you.
Avoid the 90s slacker look: if you’re pulling them up from your backside every five minutes, you’re wide of the mark. Baggy jeans should fit at the waist, even if they’re generous from that point down.
Skater and carpenter pants are a good place to start. Carpenter-style jeans are roomy by design, giving tradespeople space to manoeuvre in the workshop. They also tend to be straight-cut, and combine well with other workwear staples.
Skater styles are usually what you’ll find if the jeans are labelled ‘loose’ or ‘baggy’. They’ll be wide throughout the leg and less structured, usually leaving a degree of pooling at the feet.
How low can you go?
After width, length is your next consideration. Baggy jeans are usually worn one of two ways: cropped or puddling. Wide, cropped denim usually references skate-punk references from the 90s and 2000s, styled with white sports socks and a pair of Vans. You could also try them cropped with sandals or loafers in the summer.
If you’re going longer in the leg, then it usually means the denim pooling over your sneakers much more than they would with slimmer cuts.
Which rinses work best?
You’ll find most of the usual denim colours and rinses in baggy fits. Light and stonewash are probably the most common, because they are the ones that hark back to those 90s references.
Darker indigo styles are less common but you can find them, along with black jeans, off-white jeans and grey styles which also come in wider options.
What to wear with baggy jeans
This is an open question with a million correct answers, but let’s break it down by casual looks and slightly less casual looks. For the former, think streetwear: statement T-shirts, printed shirts, hoodies and sportswear (everything from basketball jerseys to football shirts are trending right now).
Moving an inch along the smart-casual spectrum, workwear looks great with baggy jeans. Think flannel shirts, heavyweight tees and chore jackets. Then keep going in that direction, and there are preppy ways to style baggy jeans, too – anything from a boxy-cut rugby or Madras-check shirt to a letterman-style cardigan or jacket.
One last reference to check out is 1950s denim, styled with casual shirts and leather jackets. The rockabilly look is throwback in a different kind of way but recalling the likes of Marlon Brando or James Dean is never a bad thing.
Baggy jeans outfits for men
Black baggy jeans and bomber jacket
Baggy jeans love a baggy bomber jacket. The combination is streetwear 101, especially with a hoodie and plain white tee layered underneath. Black, grey and white is also a classic colour combo, and looks great assembled in light-to-dark layers like this.
A chunky pair of Air Force 1s would be many people’s ideal footwear for a fit like this. For something a little more original, try a nubuck work boot, desert boot of moccasin-style suede shoe.
Light wash baggy jeans and cardigan
Here’s a fine example of how baggy jeans can slot into a clean, almost tailored look. The wide pants are straight and mostly crease-free, matching the plush V-neck cardigan.
It’s a smart take on classic streetwear. Light wash jeans with an oversized white T-shirt is a no-brainer, while the addition of a cardigan nods to the skate scene’s love of your grandad’s favourite knit.
The outfit is finished off with a snapback and chain – smarter-than-average accessories that also help to lift the look.
Off-white baggy carpenter jeans and striped shirt
With the right colour and the right fit, you can wear baggy jeans like a dapper pair of tailored pants. It won’t work with stonewash jeans but a rich, creamy tone like this one pairs nicely with a smart (if summery) shirt and sockless loafers.
As well as showing a little ankle, the rolled-up hems give the jeans a smoother line through the leg, helping to elevate the style.
Black baggy jeans and oversized sweater
Baggy jeans don’t always have to be statement or slouchy. Styled with a normcore sensibility, they can bring something quietly elegant to an outfit. Here’s a good example of how it’s done: the look is tonal and uncomplicated with a generously fitted knit to match the denim.
There are clever styling touches throughout though. The French tuck on the sweater is louche, as is pairing a shiny pair of tassel loafers with a pair of ‘off-black’ jeans.
Light wash baggy jeans and denim shirt
Nobody would ever claim that a heavy pair of jeans is breezy, but they can certainly give that impression. A loose-fitting pair of light-wash jeans worn with a tee and an open shirt is an easy way to do summertime smart-casual.
This outfit adds a little double denim to the mix (triple if you include the bag), with the rich blue shirt popping against the lighter jeans.
Finish the look with some box-fresh skate shoes.
Wide-leg raw denim jeans and chore jacket
Here’s another good example of how to wear baggy jeans in a way that looks considered and smart-ish. Taking notes from classic workwear with the chore jacket and beanie, the jeans look perfect – cropped, tapered and widest through the thigh.
Despite the workwear staples, this isn’t rough-and-ready menswear. The addition of the polished Derbies and mock-neck knit lift the look to something that’s more than appropriate for the office or dinner.
Baggy light-wash jeans and tucked in white T-shirt
One thing that baggy jeans give you when you style them well is proportion. Make the most of it by tucking a simple tee into your jeans and exaggerate the silhouette.
In this example, the jeans are also high-waisted with a double-height waistband. Through the leg they’re generous but not overly baggy, then taper into the pinrolled hems to show off some eye-catching sneakers.
Black baggy carpenter jeans with flannel shirt
In the last few years, it feels like streetwear and classic workwear have been drawn into each other’s orbit, with staples from each coming together in interesting ways.
Baggy jeans are right at the centre of this Venn diagram. As this outfit shows, a pair of carpenter worn with a heavy check overshirt effortlessly brings the two styles together.
Without the cap and some work boots instead of sneakers, this guy could be going to call the shots at a construction site. But with those accessories, he’s more likely to be queuing up for the latest drop from Palace.
Black baggy jeans and quarter-zip sweater
Preppy menswear and hip-hop fashion often hold mirrors up to one another and it’s another clash of styles where baggy jeans work perfectly.
Take some loose-fit black jeans and a premium hoodie or quarter-zip top and you have the makings of an outfit that looks the part whether you’re in the stands at a hockey game or making your way to an album launch party.
In this near-blackout look, the addition of a white tee adds a little contrast, while the cap keeps the look low-key.
Light-wash baggy jeans and check shirt
Proving again that baggy jeans can bring different styles together, this looks mixes surf and skatewear with something that could be interpreted as grungy or a little bit preppy depending on your tastes.
Wide stonewash jeans always work with an open checked shirt and a tee underneath, and it’s an outfit that requires little to zero thought.
The Madras check on this shirt makes it a touch more preppy than a buffalo check or plaid, but you’d still look the part at a Pearl Jam concert.
Baggy off-white jeans and cardigan
‘Baggy’ and ‘minimal’ aren’t words that always go together, but they should do. If the proportions of your fit are giving extra, then keeping the colours and patterns to a minimum is a good way to show off the silhouette.
Here, off-white jeans work with a summery tonal combo of a white tee and minimalist sneakers, while the dark cardigan gives the contrast.
Loose-fit jeans and a slouchy cardigan are a match made in laid-back heaven, and you can style it grungy, preppy or even, as this look shows, in a quiet luxury kind of way.
Baggy black jeans and bold bomber jacket
Some people find streetwear a little daunting. It’s often loud, bursting with character and different rules apply compared with other dress codes.
But streetwear outfits don’t have to be complicated and one of the easiest to wear is a pair of baggy jeans with a hoodie, an oversized bomber jacket and your favourite pair of sneakers.
It’s a combo that’s worked since the 80s, and you can mix up the colours and denim washes however you like. It’ll still look great.
Baggy light-wash jeans and black baggy shirt
Baggy clothing doesn’t have to be crumpled and slouchy. As this loose-fit outfit will attest, it can also mean sharp lines and flattering silhouettes.
To make it work, you need some baggy jeans that finish at your ankle. Give them a good press and style them with an open summery shirt and a white tee or vest underneath.
For a little Miami-tinged flair, finish the look with a pair of shiny black loafers and white socks.
Light blue baggy jeans and rugby shirt
The best preppy outfits usually come in generous fits, rather than anything too form-fitting. Think roomy sports coats, laid-back rugby jerseys and comfortable button-downs. That’s why baggy jeans fit seamlessly into a preppy wardrobe, matching the proportions of the staples that are already hanging up.
In this example, it’s a tucked-in rugby shirt worn with a light wash balloon-fit pair of jeans (pleats included!).
It’s a casual look but bonus points to the woven belt around the waist which elevates the fit and gives some contrast between top and bottom, too.
Light blue baggy jeans and beige sweater
One of the best things about 90s menswear was how uncomplicated it was. For those of us who remember it, we just cared a little less – or rather, we didn’t overthink things like we often do today.
So here’s to kicking it back 90s-style, with a very simple jeans-and-sweater combination. On paper it’s boring – stonewash denim with a beige knit – but the baggy jeans keep it interesting, especially when finished with a smart pair of black shoes.
Baggy double denim
Double denim with a baggy twist is a solid option for anyone with even a passing interest in streetwear. This example is another workwear-infused take on streetwear: a mechanic-style shirt (very 50s Americana) worn with matching jeans and a staple grey tee.
The look would be just fine with a pair of sneakers, but as we keep saying, mixing up the style codes is a good way to show off your menswear credentials. A jazzy pair of loafers spices up the otherwise causal outfit.
Baggy white jeans and black T-shirt
More minimalist streetwear here and another reminder that you don’t have to overcomplicate things. The skatewear-inspired outfit is just two colours: black and off-white, with the baggy jeans and matching loose-fit tee an easy combo for a laid-back summer.
Don’t forget the accessories: it’s arguably the cap, jewellery and statement Sambas that are the standout pieces in this look.
Light blue baggy jeans and grey denim jacket
Grunge and summer aren’t always an easy pairing but a baggy pair of light-wash jeans is a good starting point. These ones are worn long so that they puddle (intentionally) around the ankle.
It’s another double-denim look, this time with a tonal twist. The stone-coloured trucker jacket matches the jeans while yet another plain white tee serves as a trusty base layer. You can never have enough of them.
Light blue baggy jeans with suede jacket
There’s something distinctly Spanish about this combination of light-wash baggy jeans with a tan suede jacket.
Everything’s deliberately loose, again in that pointedly 90s way: the wavy white shirt, unstructured jacket and loose-fit jeans all working together.
Even the shopper-style tote bag is a whopper. Sometimes, more is more.