Blazer With A Hoodie: How To Nail This Tricky Combination (12 Example Outfits)

Smart-casual dressing isn’t always a headache-inducing grey area of menswear. Sometimes it’s as simple as pairing one smart item with one casual item and letting the contrast do all the talking. Sneakers with a suit is one example. Layering a denim jacket under a tailored overcoat is another.

But perhaps the starkest example of this opposites-attract approach is wearing a hoodie with a blazer. The combination of slouchy sportswear and a formal jacket is defiantly contrarian, rejecting two established dress codes to create an eye-catching hybrid instead.

It’s most often worn as a minimal, athleisure-influenced look, but modern preppy brands are also using hoodies and other elements of streetwear as a retro-modern callback to the sporty origins of the Ivy League look.

Why a hoodie and blazer?

Upmarket leisurewear was a thing even before the Covid lockdowns, but ever since, it’s become a mainstay of quiet luxury. Wearing a hoodie under a blazer fits in with that vibe: a high-flying mix of business and leisure that gives the impression of a laid-back member of the jet set.

Equally, the combo can be used to subvert smarter dress codes, the hoodie bringing a roguish element to what is otherwise a business-casual outfit. In this sense, the mood board is surprisingly varied: all at once, it brings to mind deliberately dishevelled TV detectives, classic preppy uniforms or the kind of 90s indie kid whose trademark look was wearing a hoodie under a long overcoat.

It can also be practical, of course, adding an insulating layer to a tailored look. Padded vests under suit jackets are now a verified part of the Wall St uniform – is the hoodie next?

12 hoodie under blazer outfits for men

Olive green blazer over white hoodie outfit

If you’re going for a colour contrast with your hoodie and blazer, it might seem natural to make the hoodie the colour pop. This look shows that doesn’t have to be the case. Match your hoodie to your trousers and make the blazer the point of difference instead. 

In this case, this icy-white base proves that hoodies can look smart with a pair of tailored pants (and even the pocket square tucked into the jacket). Then the blazer itself cements the dressier take on the combo, while the grey-green colour provides the contrast. 

Jeans with a white hoodie and navy blazer outfit

Can a hoodie ever look as pristine as a formal shirt? Maybe not, but this one runs it close. Not only is it a brilliant ivory colour, its heavy material gives the hood a structure that mirrors the sharp lines of the jacket and calls to mind the angles of a collared shirt. 

A shout-out to the accessories, too. The handsome navy blazer uplifts both the jeans and the hoodie, but it’s the shawl-like scarf and well-polished Derbies that bring the whole look together. 

Navy hoodie under a navy suit outfit

Athleisure, meet tailoring. Tailoring, meet athleisure. This combination of navy suit and navy hoodie works seamlessly, even though you’d find them at opposite ends of the smart-casual spectrum. Both elements are relaxed, minimal and slim-fitting, giving a casually elegant finish.

Another doff of the cap to the accessories here. The sporty sneakers balance out the hoodie while also chiming with the white tee underneath it.

The whole look is only two colours, but it looks sophisticated and thought-out.

Grey hoodie under grey tweed blazer outfit

When the look is tonal, a hoodie under a blazer quickly makes sense. In this case, a less formal blazer complements turn-up corduroy trousers and a slouchy, textured hoodie.

The blazer itself is an unlined herringbone design that adds another element to what is already a tactile outfit.

Fit is also key in this look, with each element cut for a relaxed silhouette. This makes it easy to wear the blazer over the top of the hoodie but it also gives the outfit some versatility.

Are you going to an art show? Are you running out to get hangover supplies? Who knows!

Navy technical hoodie under a grey blazer outfit

Who says sportswear can’t be tailored? This all-jersey look from Hugo Boss gives sweats a suave makeover, the matching hoodie and joggers cut slim and athletic.

Over this, the soft jersey blazer looks completely at home with a relaxed, comfortable drape from the shoulders. 

Navy, grey and white is an all-seasons no-brainer and one that works with both sportswear and tailoring. No wonder it looks slick on a combination of the two.

Grey hoodie under a navy blazer outfit

Here’s Hackett to showcase again how easy neutral colours bring together the smart and the casual elements of this combination.

Repeating layers of grey, white and navy give the look a little depth with a limited palette and the zip-up hoodie again matches the chinos.

More preppy than the previous example, the off-white pants give a more tailored vibe than smart joggers, while the minimal white sneakers are a natural partner for hoodie-and-blazer fits. 

Grey technical hoodie under grey unstructured blazer

Technical hoodies and zip-up running jackets are trickier to pair with tailoring than jersey items because the sportier cuts and fabrics contrast a little more sharply with blazers and smart trousers.

That’s not to say it can’t be done. In this example, the monochrome grey softens the contrast for a fashion-forward vibe. 

If you’re wearing a more technical hoodie with a blazer, keep the jacket unstructured and lightweight for a more natural pairing. You can also wear a more technical sneaker with this combo.

Navy hoodie under green-blue blazer outfit

There are preppy staples from head to toe in this outfit: chinos, sports coat, Madras-check shirt and a casual cap to top it off. It’s a layered, colourful take on 60s campus dress, with the hoodie slipping naturally under the blazer.

Few style tribes combine athletic and tailored clothing as well as preppy dressers and placing a a zip-up hoodie between a blazer and shirt is a pro-level move.

The look also shows how hoodie-and-blazer outfits don’t have to come in stripped-back colours. Note how the upper-body colours get progressively darker with each layer and how the pink cap picks out an accent from the check shirt. That’s no accident.

Patterned hoodie under charcoal cord blazer outfit

Wearing a patterned hoodie with a blazer or any kind of tailoring is a minefield, but it’s easier when the look leans into the streetwear aesthetic.

In this example from luxury Italian outfitters Kiton, both the blazer and the hoodie are plush and relaxed, but muted too. The flashes of blue on the hoodie are a subtle injection of colour in an otherwise a dark and tonal fit.

Relaxed-fit corduroy is a good material to opt for with the blazer. It’s naturally more casual than traditional wool or cotton and also gives college campus notes, which help it pair with the hoodie.

Brown hoodie under a dark brown blazer outfit

Wearing a hoodie with a blazer is always going to look languid, but you can lean into the slouchy style by making both the jacket and the trousers loose fitting.

This outfit is all about the drape, the crease and the attitude it projects. The jersey blazer sets the tone in this look, the link in the chain between the ultra-loose trousers and the generous hoodie.

With a pair of sneakers, this look would lean sporty, but the inclusion of some polished Derbies elevates the whole look to something you’d expect to see on a modern runway. 

Ivy league hoodie under a blazer outfit

Here’s another positively preppy way to wear a hoodie with a blazer. It’s Ivy League to the core, from the loafers and green socks right up to the denim shirt under the hoodie.

As with so many of these outfits, contrast is king, the herringbone jacket (complete with ruffled pocket square) playing off the sporty stripes of the hoodie.

It’s a very particular corner of Americana, but if you find it a bit niche, you could swap the loafers for skate shoes, lose the pocket square and the look would still give an individual take on smart-casual menswear.

Bold yellow hoodie under a navy blazer outfit

Colour-pop hoodies look great whatever you wear them with, but they look particularly good if you style them well with tailoring.

This one, in a bright canary yellow, shines against the classic navy blazer and trousers and there’s even a hint of a Breton top underneath. 

As ever, fit is key to making it work. The hoodie is big and comfortable, so the blazer has to be unstructured to accommodate it. And let’s give a shout out to the well worn Chuck Taylors, which land the whole look in a Wes Anderson-style version of indie menswear.

5 tips for wearing a hoodie with a blazer

Keep the blazer loose

There’s no way the same blazer will fit right with both a thin dress shirt and a heavy hoodie. So if you want to wear this look well, you’ll either need to go a size up from your usual tailoring or opt for an intentionally oversized, probably unstructured jacket.

Keep the hoodie smart

Remember, the vibe is luxury leisurewear. You can’t wear the same years-old favourite hoodie that’s accompanied you to the gym, on flights and through many a Netflix binge.

You need a ‘smart’ hoodie, one that fits quite slim and is soft to the touch. Zip-ups and popovers both work so long as they’re in like-new condition.

Think about fabrics

Making a hoodie work with the average cotton blazer is a hard ask, but not impossible.

Stay away from anything too plush or shiny because the look works far better when the blazer’s fabric is more textured. Think jersey, herringbone, corduroy or wool. If you are going with cotton, keep it flat and matte. 

Be particular about your palette

Broadly, there are two ways to think about colour on an outfit like this: go tonal or create some contrast. A simple way to make it work is to match the colour of your hoodie with the colour of your jacket, your trousers or both. This ensures the styling is slick and deliberate.

The alternative is trickier to pull off, but can be more visually impactful. Use bold colours or stark contrasts between the hoodie and blazer to draw more attention to an already-eye-catching look.

Bring it together with accessories

Wearing a hoodie with a blazer can be incongruous if you don’t mirror the contrast of smart and casual with other elements of the outfit.

If it’s a relatively smart jacket and trousers, the hoodie will make more sense if you’re also wearing sneakers.

If the look you’re going for is more preppy, consider other Ivy League accessories such as penny loafers or a cotton cap.