Time To Take Your Hoodie Off The Couch And Onto The Street.
It’s hard to pinpoint exactly when the hoodie moved from functional to high fashion. It’s been a slow burn since the ‘30s when the now ubiquitous item was first designed as a way to keep athletes’ ears warm. Hip hop culture had its part to play as early as the ‘70s, and various subcultures since have appropriated the hooded sweatshirt as a symbol of insubordination or acceptance depending on which way you look at it. It’s only over the last decade the hoodie has really hit the mainstream in terms of a fashion look. High end designers and street style stars are partly to thank for the seismic shift in thinking, with new generation musicians like Billie Eilish cementing the trend. Add in a global pandemic where home has become the heartland and the hoodie steps to centre stage.
So, how to style a hoodie?
There’s no one way.
It pays to be more specific when narrowing down what works best for you. How to wear a hoodie to work might be the more productive question. The answer: the hoodie and blazer outfit. How to dress up a hoodie? Let’s just say the solution involves glossy knee-high boots, but more on those later.
What it really comes down to is finding your hoodie style. Whether you’re from the prep school of thinking or you lean more towards glam-grunge, it’s about the pieces you choose to pair it with that’s going to take your hoodie from the living room to larger life.
You may be the type who already owns one in every colour and conceivable length, but if you’re just starting out, two styles should cover almost all the hoodie outfits you could want to try. Enter the grey marle hoodie - a non-negotiable that will probably take its rightful place as the most worn item of clothing you own. It works with pale and darker tones, denim and dresses equally well. For maximum versatility, opt for a longer line in a slim cut (think sleek, not sloppy) with a joey pocket and long sleeve that will layer well under jackets.
Your second purchase? It’s the cropped hoodie. Admittedly more trendy than her big sister grey marle, she’s just as adaptable and works well in a soft dirty pastel for a seasonal wardrobe update.
Whatever hoodie you choose, make sure you look for fabrication first. A soft loop-back terry material will wear well and feel great on. And keep a look out for sustainably sourced cotton in a jersey finish. Then all that remains is some clever outfitting and you’ve got yourself some cool, cosy and comfortable looks that get the tick of approval for almost any social setting. So, read on for nine ways to style a hoodie that will revolutionise the way you dress, on and off the couch.
- Hoodie plus D-ring pant
This could possibly be the chicest way to style your hoodie we’ve seen yet. A casual top with a tailored pant and the boot of the season: so simple yet so effective. Let’s start with the hoodie, because everything will flow from there. Your cropped version in a fashion colour - in this case, faded terracotta – is perfectly placed here – just long enough to tuck the edges into the waistband without having excess fabric to complicate things. It’s also worth noting, the gold hardware on this version adds a luxurious touch. When it comes to the pant, a belted style that sits high on the waist feels most current, and a cool shade of cream feels rich and refreshing, especially through winter and spring. Detail is important here in terms of the belt – the D-ring style links back nicely to the utilitarian origins of your hoodie while still appearing polished. As for the boot – white, ankle height and softly pointed with a heel will be your trend investment of the season; paying dividends every time you get dressed.
You will find with most, if not all of the hoodie looks we’re deconstructing, it will pay to opt for a pulled-back hair style if you have long hair – with a hood it can be hard to manage. Plus, you’ll want to maximise the flattering drape a hood creates around the neckline. We officially give you permission to have a day off from perfecting your locks.
Proportion inevitably makes any outfit more interesting. It’s all about the crop here: cropped hoodie, cropped pant, cropped boot, the proportion is what makes the look. Get that right and the rest will take care of itself.
- Hoodie plus bomber
One of our favourite ways to style a hoodie is to take it back to its streetwear roots. Enter, the quilted bomber.
Originating from military clothing, it’s a piece that’s been appropriated by subcultures ranging from punk to grunge and has survived the test of time as a lightweight, versatile, and genderless must-have that is equally fashion and function. Team it with winter’s other big trend bubbling up from the street – the snug-fitting beanie, and luxe sweatpants for go-anywhere, do-anything style.
Footwear can really make a difference when it comes to choosing who you want to be in your bomber.
- Hoodie plus aviator
There are few jackets that come with such a loaded history as the aviator does. The classic sheepskin flying jacket was first designed in the early 20th century and still speaks of romance and adventure today. To say the hoodie – a piece that comes with its own chequered history of nonconformity – makes for a perfect match would be an understatement. Together, they make a formidable style partnership. You could just as easily team them with black denim and a sneaker boot as you could a leather pant and stiletto heels – in either scenario, they would hold their own.
This jacket is to be worn ‘shrugged on’, so leave it unzipped and belt buckle hanging if the weather allows. And it might seem obvious, but remembering to free your hood from the collar is essential – the padded collar should give the fabric a nice lift so the hood hugs your neck. Remember, long hair up.
Whatever you choose to wear down below, keep it slim through the leg. The aviator is the feature piece here and it’s naturally going to dominate. A straight or skinny jean or unfussy tapered pant in a toning colour, or in this case non-colour, will provide a good balance.
- Hoodie plus stonewash denim
This look is what ‘80s dreams are made of: the grey marle hoodie, stonewash seamed denim, the box-fresh white boots. The whole combination harks back to a time when sportswear was acceptable in almost any situation. Only, thanks to updated fits and modern detailing, it feels firmly rooted in the now – so pack away your leg warmers. The hoodie would absolutely work with a plain blue vintage wash denim, but something about the stonewash takes it to the next level. And the style of jean, almost like a jogger, feels like a trend piece but will become and ongoing and indispensable go-to. A basic that doesn’t make you feel basic: push up your sleeve and you’re good to go.
The waistband of these jeans is too good not to show off. A loose tuck of your hoodie has the twofold effect of giving this look stylish slouch while also creating a flattering mid-point. You could also easily swap in your cropped hoodie here for a similar aesthetic.
With their front seam, high waist and volume through the calf, these jeans are definitely a feature piece, and they deserve to be shown off atop a sleek ankle boot. Take note of where the cuff ends so you can choose your boot accordingly – denim and leather should meet in the middle with little-to-no skin showing. Lastly, a heel – even if only a few centimetres – will provide a flattering boost and positively counteract the volume through the leg.
- Hoodie plus coat
It’s amazing what a good coat can do. Taking the most basic of winter outfits, an overcoat can transform it into a super chic proposition, even if you are just heading for a supermarket shop. It feels like a very Parisian approach to dressing, giving off an effortless vibe while at the same time looking incredibly put together. The key is in the cut of the coat: minimal, generous, and warm without being bulky and it’s the quality of the pieces that counts. This look, for example, is virtually worked around what amounts to a tracksuit, but the fabrics are luxe, and the fit is spot on. The unexpected addition of a boot provides the cool-girl twist. Take it to the gallery opening or your Saturday lunch booking.
Swap your wool coat out for a trench coat when the weather warms up. Classic hues like navy or camel would work just as well as winter khaki and the principles are just the same. If your coat is belted, tie it to the back, leaving the front hanging loose for the ultimate style insouciance.
Longer lines work well here, so a more generous hoodie and a coat that falls to the knee works well. The high heeled boot, toned in with the colour of the pant, serves to create a leg-lengthening effect, so you can afford to go for more fabric up top without the fear of your frame being swamped.
- Hoodie plus oversized blazer
Never thought you’d be able to get away with walking the hoodie through the office door? Here you have it: the workwear hoodie in all its glory. This is no work-from-home look we’re talking about. This is bona fide, meeting room-worthy, seat at the table stuff. The piece that holds this look together and keeps things business-appropriate is the blazer. Roomy enough to fit comfortably over the hoodie and still have space to spare but tailored enough to keep a crisp line across the shoulders and drape sharply from the collar, an oversized blazer instantly smartens up sweats. Teamed with a tapered trouser and sleek boot, it’s a cool-come-creative spin on the classic suit that says you’re the type who thinks outside of the box.
This look feels modern and fresh and it’s owing to the light and neutral colour palette and the addition of fresh white. The chocolate brown accessories add an element of luxury that’s not stark like it would be if the bag and boot were in black. That’s not to say this look wouldn’t work in dark tones: quite the opposite. It just wouldn’t strike the creative pragmatic note that the casual grey hoodie layered under pale mushroom blazer does here.
When it comes to choosing a bag that works with your big blazer and hoodie combo, bite-size is better. Anything with a shoulder strap is going to ruin the shoulder line of your jacket, and anything resembling a tote is going to make your jacket seem bulky. The contrast of big and small here pulls this look together and gives you a cute excuse to push up your sleeves – a must if you want to appear to be wearing this outfit with ease.
Model in women's hoodie, oversized blazer, white denim jeans and boots
- Hoodie plus floral skirt
This is the dawning of the age of a sartorial mash-up. A ‘70s tiered floral skirt worn with a sporty noughties hoodie and a 2021 take on the ‘60s go-go boot is pure genius as far as successful style scrambles go. The reason why this works is that no element is too fussy; each piece is streamlined and sophisticated in its own way. And the pretty-versus-practical combination is timeless, with the hoodie preventing the skirt from becoming too ladylike and the skirt elevating the hoodie. It’s a win-win. Then the white ankle boot steps in, skimming the hemline and kicking the whole look into the realm of ‘fashion’.
Imagine if the print on this skirt featured brightly coloured florals. It would be way too garish, right? But the fact that this pattern is dominated by ‘off’ retro shades of mustard and khaki with a sprinkling of white means it becomes a non-pattern. There, but not overshadowing you or your look as a whole. It also happens to be a colour palette that is extremely on trend right now so, bonus.
Notice the jumper tuck. It goes against every instinct to tuck a hoodie in to anything, let alone a light, fluid skirt. But that’s also exactly what balances this look and keeps it from veering into frumpy territory. Notice the outfit is broken up into thirds – the hoodie is one third and the midi skirt makes up the remaining two thirds. Using this equation, if you were to team your hoodie with a short, flippy skirt (which we would absolutely encourage) then you would leave it untucked, retaining the 1:2 ratio. Easy.
- Hoodie plus parka
There is much that goes into choosing the perfect parka jacket. It’s a kind of forever piece that will come in and out of your wardrobe season after season when the temperature starts to drop and the windchill factor starts to rise. It will accompany you to everything from the backyard barbecue to the football match, Saturday sports practice and the morning coffee run – so you want to get it right.
We think there are a few boxes to tick before welcoming one into your life. Firstly, is it big enough to easily fit over your hoodie? There is truly nothing worse than the stiff arms that result from a jacket being too small to fit over anything substantial underneath. Secondly, does it have roomy pockets? It goes without saying that you need somewhere comfortable to hide your hands away when the frost sets in. Next, is it easy closure? A simple zip hands down trumps any tricky fastenings. And lastly, is it something you will enjoy looking at long term? And that’s only something you can answer. Colour, detail and finish are all personal choices and all elements to consider when you think this is a piece you will return to time and time again. The addition of a hoodie will just make everything better.
You could play it safe with this look and opt for a pair of sneakers but there is something unexpected about teaming this jacket and hoodie combination with a combat boot that we love. It takes the outfit from sports to street, especially with dark denim in between.
There is certainly a place in your wardrobe for a coverall parka that stretches to your knees and comes complete with hood. However, this neater style gives you the versatility that bigger styles may not. Choosing a cropped cut that sits snugly at the hips is a clever alternative that lends itself to layering over your shorter hoodie for warmth without the excess volume.
- Hoodie plus over-the-knee boot
Welcome to advanced level hoodie styling. This look hits it out of the ballpark in terms of high-low dressing. Let’s skip straight to our favourite element of the outfit: the over-the-knee (mock) crocodile stamped leather boot. Very cool, very subversively sexy and very right pulled up over a pair of leather leggings. If you’re looking for a way to take your hoodie out with you on a Saturday night, this would be it. Teamed with a crisp shirt, it feels super dressed but super laid-back at once – not an easy thing to achieve. This is the kind of comfortable, confidence-building ensemble that will help you stride into that bar like you own it.
With boots like these, you can afford to keep your grooming super low-key. Natural make up that defines your best features (a strong brow, a high cheek) and swept back hair is all that’s needed. The less it looks like you tried, the more interesting the look becomes. And remember to pop that white shirt collar – it’s a fantastic face framer.
This is a job for your longline hoodie. The thigh-skimming length almost feels like it could be a mini dress but leaves room for the white shirt tails to peek out underneath. This flash of white is essential because it balances out the collar and cuffs, otherwise the shirt effect would get a little lost (or feel a bit half-hearted). And we need that shirt element, because the masculinity it brings balances out the femme fatale factor of the boots. Again, it’s all about the yin and yang.