Men’s Fall Fashion Guide: The Key Pieces, Trends & Looks For 2023

A fashion insiders guide to fall 2023. Includes the key pieces, fashion trends and styling tips you need to know.

Hands up if you’re bored of shorts and T-shirts. Us too. Sure, it’s fun for a while, but when the nights begin to draw in and the temperature starts creeping downwards, we can’t help but feel a sense of relief at the imminent sartorial freedom fall is about to grant us.

Those golden-brown leaves are your cue to rediscover the other 90% of your clothing. Big coats and boots have been buried at the back of wardrobes for months now, but it’s time to dig them out, dust them off and brush up on your cold-weather style as we wave goodbye to the sun for another six months. Not only that, it’s an opportunity to invest in some new seasonal pieces – but first you need to know what’s hot and what’s not for fall 2023.

From the the key garments every man should have in his transitional rotation to the fashion trends worth paying attention to  – here’s our carefully curated men’s fall fashion guide. Consider it your style cheat sheet for the coming months. You’re welcome.

Key fall 2023 pieces

Worker pants

Utilitarian trousers with pouches and pockets aplenty are a big trend and have been for some time. It’s a good one to jump on as it’s actually highly practical, not to mention nice and easy to style.

Trousers like these are thick, durable, comfortable and perfect for everyday wear. Check out the likes of Carhartt’s iconic Double-Knee pants and Stan Ray’s Painter Pants for two of the best options. Oh, and go vintage for extra points.


Cardigans have been back en vogue for a couple of years now, with one key rule: the hairier the better. Brands like Needles and Beams Plus are making some rather fetching fuzzy options, which are great for bringing texture to transitional outfits, and layering up as the cold starts to bite.

Fleece jacket

Thanks to so-called gorpcore, outdoorsy pieces are enjoying renewed interest outside of campsites and mountain trails. One such garment is the fleece jacket, which has gone from birdwatching essential to must-have fashion item in the space of just a few short years.

Thick-pile versions are the most sought after, with vintage Patagonia Retro-X fleeces going for silly money online, but there are plenty of alternatives to get stuck into, thanks to the fact that pretty much every outdoor and preppy brand out there is now pedalling its own version.

Heavy overshirt

Overshirts are great all year round, but they work particularly well in thicker, textured fabrics during the colder months. Think wool, corduroy, tweed, flannel and even suede.

Whichever material you pick, it’ll make a versatile addition to your fall/winter wardrobe, and you’ll probably be surprised at just how much use it gets.

Wool overcoat

A proper wool overcoat is something of a miracle garment. You can throw it on with anything and everything, using it to dress slouchy weekend outfits up or tie smarter looks together.

Buy a good one and it’ll last you for as long as it’s looked after.

Puffer jacket

As the mercury plummets, there are few fall jackets better equipped to keep you warm than a good old puffer. With oversized baffles stuffed full of down insulation, these sleeping bag-like jackets are cosy, stylish and surprisingly lightweight.

Go for a boxy, oversized fit for a retro aesthetic that works well with streetwear, or keep it modern with something that sits a little closer to the frame.

Stonewash jeans

Why not save the raw denim for winter and hang onto lighter shades for a little bit longer? Light stonewash jeans have a more laid-back air about them, which makes them perfect as a foundation for weekend outfits throughout the fall.

We’d suggest sticking with a classic tapered fit, and avoiding anything overly loose or slim.

Textured unstructured blazer

Sometimes you need to dress up without actually dressing up, and that’s where an unstructured blazer comes in. It’s relaxed and informal, but still conveys the message that you’ve made an effort.

It’s easily dressed up or down depending on the setting, and looks particularly great in textured fabrics like wool and cord.

Chunky Chelsea boots

Chelsea boots are great for fall and winter, particularly when they have a nice beefy sole unit on them to cope with all the slippery pavements and fallen leaves.

A huge footwear trend right now, commando soles look great on Chelseas and are highly practical too. Wear your Chelsea boots with denim, knitwear and substantial outerwear, like a parka or puffer.

Premium hiking boots

Upscale hiking boots make an excellent alternative to work boots or Chelseas. They look great, they’re practical and, if you buy right, they’ll last you for years.

Go down the traditional leather route for a classic look with brands like Danner and Fracap, or take a contemporary approach with a technical design from the likes of Diemme or ROA.

Key fall 2023 materials


Men's blue jeans, brown leather boots, white fleece jacket and baseball cap outfit


Not only is fleece an excellent insulator, it also has a completely unique texture which can bring a new dimension to your cool-weather looks.

It comes in a few varieties, but the key thing that differs is the ‘pile’, which ranges from low-profile ‘micropile’ to thick high-pile fleece. The latter is highly textured and almost reminiscent of a sheep’s coat.


Men's black trousers, black T-shirt, corduroy overshirt, beanie and high-top sneakers outfit

Wax London

With its raised strips of fuzzy fabric, cord is another solid option when it comes to jazzing up your fall fits with a touch of texture. It works well on pieces like blazers, overshirts and trousers, but just make sure you limit yourself to no more than one corduroy garment per outfit.

Fail to do so and you risk straying into the dreaded geography teacher territory.


Modern office outfit for men with chinos, shirts and jumper with chelsea boots

Luca Faloni

If you can afford to add some cashmere to your fall/winter wardrobe it’s something well worth doing. This high-end fabric is super-soft, insulating and comfortable – bringing a touch of luxury to your daily fits.

Plus look after it well and you’ll get your cost per wear out of it.

Heavyweight jersey

Pale stonewash denim jean jacket outfit for men with tracksuit and boat shoes

Aime Leon Dore

Whether it’s a crew neck, hoodie or joggers, we say the heavier the better when it comes to your staple jersey-cotton pieces. Anything above 12oz can generally be considered heavy for this type of fabric. What that means for you is warmth, durability and comfort.

Men’s fall 2023 fashion tips

Layers, layers, layers

Layering is one of the cornerstones of stylish fall and winter dressing. When shopping for new clothes, or just piecing together new outfits from your existing wardrobe, put some thought into how garments will layer with one another.

You want your outerwear to be loose enough to wear over a hoodie, a fleece or an overshirt, and base layers to be fitted so as not to bunch up when you throw something else on top.

Big coat energy

If you buy yourself one thing this fall, make it a big winter coat. We’re talking something thick and warm that you can throw on over anything and everything without too much thought.

A wool overcoat is a timeless option, perfect for making even the most slapdash of outfits appear stylish and considered. Hell, you can sling one over a hoodie and sweatpants and it’ll still look good.

Take the rough with the smooth

If layering is one key component of cold-weather style then texture is the other. Mixing different fabrics creates depth and focal points within outfits, and takes your fall looks to the next level when executed well.

The key here is to keep the textures varied – don’t go all in on any one material, instead aiming for balance and contrast from head to toe.

Pick and choose trend-led elements

This advice holds true at any time of the year, but it’s always worth repeating: trends are good. They keep menswear and fashion in general moving along. If they didn’t exist, we’d all still be walking around in animal pelts and loin cloths.

However, approach them with caution. Leaning too far into any single trend never looks good. Instead, pick and choose elements from different trends that complement your personal style and use them to enhance your outfits.

Tailoring revival

Tailoring is coming back in a big way and fall is the perfect time to get involved in the revival. We’re not saying you have to go full Don Draper, but even mixing the odd tailored separate into an otherwise casual wardrobe will help to elevate your look.

If you’re the sort of guy who usually shys away from suits, you could experiment with unstructured blazers and knitted tailoring, which looks smart without being stuffy and can be easily styled with more casual garments.

Either that or go full tilt and use this as an excuse to buy yourself a full double-breasted suit.

Collegiate cool

The streetwear-infused strain of preppiness that’s currently spreading through menswear’s veins shows no sign of slowing down as we progress into the cooler months. Think Supreme meets Polo Ralph Lauren and you’ll be well on your way to understanding what the aesthetic is all about.

It’s a more grown-up take on so-called ‘streetwear’, offering some interesting opportunities to shake up your style with pieces you may not otherwise have thought of. Just be careful not to lean into it too hard, instead just picking the elements that work for you and complement your existing wardrobe.

If your look leans casual, consider a varsity jacket or bold streetwear hoodie. Like to dress up? Try a high-end rugby shirt or corduroy sports coat.

Stealth mode

Monochromatic all-black fits are on the rise, which makes looking stylish very simple. All black everything is essentially a menswear cheat code that can make you look slimmer, taller and more sophisticated, even if you just selected black pieces of clothing from your bedroom floor at random.

Sweater vests

From one of the easiest trends to nail to one of the trickiest. Inexplicably, sweater vests are having a moment, but they’re not the most straightforward of garments to style.

The best way to approach it is as part of a heavily layered look. Try stacking it up with a T-shirt, an overshirt and a long coat. If you’re going for a pattern, make sure to keep the rest of the garments pared back to avoid any unsightly clashes.