Flannel Shirt Over A Hoodie: How To Nail This Classic Combination

It’s a simple look that’s as stylish as it is comfortable and warm. It’s ideal for changeable weather conditions and can be as colourful or monochromatic as you see fit. It’s equally inspired by classic streetwear, skate culture and grunge, and it suits all manner of body shapes and ages. We are, of course, talking about wearing a flannel shirt over a hoodie.

At first glance it appears easy. And while you could just throw on the nearest flannel over your favourite sweat, it can quickly look sloppy or even a bit immature if you don’t give it enough thought.

There’s whether to colour match or not, fabric weights to consider and what pants to pair with them. We cover all this and more below, while showcasing 11 outfits that get this classic combo right.

Why a flannel over a hoodie?

This is a look that’s part rugged outdoorsman, part sportswear. Today, it draws from a number of menswear niches and sub genres, and thanks to its versatility has been favoured by everyone from skaters to rappers, lumberjacks to hypebeasts.

The real beauty lies in its ease. You don’t have to think too much about it, and once you’ve got the pairing down, you can return to it time and time again. It’s also extremely practical. In fall and winter, when the weather is cold and unpredictable, a flannel shirt over a hoodie makes for a great layering option that looks cool while keeping you warm.

How to wear a flannel & hoodie tips

Colour matching

Colour is one of the main draws of wearing a flannel shirt in the first place. They come available in a wealth of vibrant shades and checks, from muted monochrome motifs through to heritage tartans and brightly coloured plaids.

You may want to wear yours as a statement piece, or you could use it to tie your outfit together. The latter is where the flannel shirt really comes into its own. With multiple colours found in its check pattern, try matching one of the base hues with your trousers or footwear for an easy menswear flex.

Consider fabric weights

This is a look that’s made for cold weather. Layer a wool flannel overshirt over a thick cotton hoodie and you’ll be warm enough virtually everywhere other than the Arctic. It’s also adaptable and perfect for days when you’re moving between indoors and out. Simply consider your shirt like you would a jacket and remove it when inside to avoid overheating.

That said, such weighty materials can feel and look cumbersome outside the depths of winter, so it might be worth opting for something lighter in weight. A shirt made from linen or a cotton/wool blend, for example, will stop you sweltering on warmer days. The same goes for your choice of hoodie – a loopback cotton version, or even a luxe merino take, is much better suited to spring and summer.

The takeaway? This is a pairing that can be adapted to every season and worn year round.

When to wear a flannel and hoodie

There’s no getting away from it, this is a casual look. You can dress it up slightly – with a black cashmere hoodie, black pleated trousers and a tailored wool overshirt, for instance – but it’s a combination that’s should primarily be kept for the weekend and laid-back occasions such as winter walks, trips out of town or the pub with friends.

It also looks its most natural and authentic when teamed with similarly casual pieces like jeans, twill chinos or carpenter pants, as well as sneakers, desert boots or chunky-soled Derbies (think Dr. Martens).

Men’s flannel over a hoodie outfits

Black hoodie and red flannel shirt

An all-black look works perfectly when a hoodie and flannel shirt are involved. But for something with a bit more visual interest, it often helps to add a pop of colour.

This can be done of course with the hoodie, either in the form of block-colour design or a logo’ed streetwear version. But try it with a red-and-black check flannel shirt for a workwear-inspired twist, and you won’t be disappointed.

Keep it classic

Flannel shirts are most commonly found in check patterns. But for a change of flavour, while still keeping it classic, seek out other traditional menswear motifs, such as houndstooth. While most often applied to tailored garments like blazers and overcoats, it works just as well in the form of an overshirt.

Combine it with other muted pieces like black trousers, a grey hoodie and monochrome sneakers and you can’t fail.

Streetwear-inspired hoodie with a flannel

Wearing a flannel shirt with a hoodie very much taps into fashion’s current obsession with streetwear, given that both garments have long been associated with skate culture, hip-hop and grunge.

Channel the aesthetic in a contemporary way with a printed hoodie, oversized shirt and high-top sneakers, completing the look with a trouser chain and baseball cap.

Sport casual

Laid back and easy to wear, this is a look that could form the backbone of your weekend wardrobe, especially if comfort and functionality are your priorities.

It consists of a set of slim-fitting, matching sweats anchored by a white T-shirt and minimal sneakers. So far, so basic. But the introduction of a slightly oversized flannel shirt with dropped shoulders elevates the outfit, giving it contemporary streetwear feel while upping the comfort factor.

90s-inspired flannel and hoodie

Hoodies and flannel shirts made up a large portion of what was popular in the world of 90s menswear. And they look as cool in 2023 as they did back then, especially when combined with a pair of suitably washed and faded denim jeans.

Complete the throwback look with some canvas sneakers for that added dose of retro skate style.

Statement hoodie and white flannel

All-white is tricky to pull off at the best of times. It’s made easier though when pattern and tone variation come into play. That means eschewing stark white and instead mixing shades of cream, stone and off-white, using the shirt to introduce contrast via colour and/or texture.

The best thing about using a neutral white base is that you can go bolder with the hoodie, as shown here. The bright blue shade pops nicely against the white and black flannel, but you could switch this for any colour imaginable, from pastel pink to canary yellow.

Denim with a flannel

There are few fall/winter combinations that are as timeless as flannel and denim. The two workwear fabrics boast an abundance of texture, complementing each other perfectly. This is especially true if you opt for dark selvedge denim and a rich shade of green for the shirt.

Elsewhere, keep things simple with a staple block-colour hoodie and suede boots for a foolproof cold-weather outfit.

Natural shades

Tonal looks typically consist of black or navy shades, but go for brown and you’ll set yourself apart as a man who really knows how to dress.

The key to getting it right, as always, is to use varying but complementary tones. Think deep chocolate brown, rich caramel and subtle hints of stone, as shown above. The sparing use of bright white is a masterful stroke that creates some much-needed contrast and lifts the entire outfit.

Oversized flannel shirt over a hoodie

For an alternative approach to wearing a hoodie with a flannel, try playing with proportion. This can be done with the hoodie, which is often looks its best slightly oversized, or with the shirt itself.

For the latter, try opting for a relaxed-fit design that is slightly longer in the body and cut from a thick wool, which will help it drape better and make it feel more like a robust piece of outerwear.

Grunge-y flannel shirt over a hoodie

An interesting way to try this look is by contrasting the top and bottom half of the outfit. You can do this with proportion, as previously mentioned, or spice things up with clashing colour palettes.

Here we take a leaf out of the grunge playbook, juxtaposing a multicoloured flannel shirt with acid wash jeans in a grey-white tone. The contrast is striking without being overwhelming, in part thanks to the black hoodie and chunky Derby shoes that ensure both pieces are given enough room to shine.

Grey sweats and a flannel shirt

If you want to upgrade your off-duty loungewear into something slightly smarter, try adding a flannel shirt into the mix.

This luxe knitted sweatpant and hoodie set is elevated by the Black Watch tartan shirt, creating a clean, minimal look that’s surprisingly easy to wear (and supremely comfortable) both in and out of the house at the weekend.