With cooler temperatures comes a cooler range of shirt options. Fall menswear lets us pull out the long sleeves, steam the heavier fabrics and generally bask in choices again after a summer of (admittedly lovely) short-sleeved linen.
Layering – layering! – is also back, and the best fall shirt styles moonlight in different roles. A versatile Oxford shirt, for example, will work under a blazer or knitwear and over a T-shirt. It’ll even look good under other styles of shirt, with overshirts becoming a cornerstone of fall wardrobes in recent years.
Below you’ll find a list of our favourite fall shirts for different weather conditions and occasions. Our advice? Get the lot of them.
Corduroy Shirt
Velasca
Corduroy is a fabric made for autumn. Corduroy shirts bring warmth and texture to the cooler months, and the material’s ribbed construction adds depth and visual pizzazz to any outfit.
It’s also highly versatile: You can dress it up with chinos or some 70s-inspired suiting or go casual with jeans. Or you can wear it as an overshirt on those early fall days when summer comes back for an encore.
Whatever the weather, corduroy shirts strike the right balance between smart and laid-back. Rich fall colours, such as deep burgundy, mustard or olive green are ideal choices for the season and complement a variety of tones in your wardrobe, but don’t discount something lighter like an off-white.
Corduroy also has a sheen that helps it work with tailoring, but more often it’s the rugged charm that appeals, coupled with an easy-to-wear aesthetic. A stylish, practical, often gorgeous bit of fall fashion.
Flannel Shirt
Velasca
The elevator pitch for flannel shirts goes like this: it’s a shirt that feels like a blanket. Enough said, right? That’s why flannel is a must-have fall shirt style, offering comfort and good looks. The soft, woven fabric keeps you warm and effortlessly cool, but its versatility is its biggest strength.
On warmer fall days, a flannel shirt works as an outer layer. When the mercury drops, it also looks great under overcoats or hiking jackets. You can wear it as a standalone piece or layered over a tee for a more relaxed vibe.
Neutral or muted tones will get the most wear, perfect for pairing with jeans or chinos. If you’re heading outdoors, bolder colours like reds, blues, or greens tap into a throwback gorpcore look.
Oxford Shirt
L’Estrange
An Oxford shirt is a year-round wardrobe staple, but it’s especially good in fall. Its thicker, slightly textured cotton fabric makes it perfect for layering as temperatures drop.
The Oxford, with its preppy credentials, offers a polished but casual vibe, transitioning easily from a day at the office (or on campus) to a semi-formal evening out. Pair it with a tailored jacket for a smarter look, or roll up the sleeves for laid-back weekend style.
Neutral tones like white, grey, or light blue are timeless, but you’ll also find darker shades such as navy or forest green for fall. We’re also quite taken with some of the more colourful or patterned versions we’ve seen in recent seasons, which work well with streetwear or jazzier takes on preppy fashion.
Denim Shirt
Velasca
A versatile and durable staple that transitions effortlessly into autumn wardrobes, a denim shirt should hang in every man’s wardrobe.
Known for its rugged charm, the style offers a casual yet put-together look that works for various occasions. It can be worn on its own or layered under a jacket or sweater for added warmth. Lighter washes provide a relaxed, laid-back vibe, while darker indigo shades are perfect for a more polished appearance.
Pair yours with chinos or dark jeans for a trusty double-denim look, or contrast it with wool trousers or even a full-blown suit for an unexpected take on fall dressing. However you wear it, this all-season all-star is perfect for men who want to add texture and depth to their outfits.
Military Overshirt
&SONS
Atten-hut. Here’s an affordable way to add something different to your fall rotation. Head to your nearest vintage or surplus store and pick up a classic army shirt in olive green. Designed for heavy wear – like, battlefront heavy – they make for a practical autumn layer and offer structured, masculine styling at the same time.
The utilitarian nature means they work well with denim or combat trousers, but we prefer to style them with something more refined. The green looks great against off-white jeans or navy tailored pants and the clash of styles makes for a more memorable outfit.
Brushed Cotton Shirt
Luca Faloni
Brushed cotton offers an unbeatable combination of softness and warmth, making it a standout fabric choice for fall shirts. The material undergoes a process where the cotton is (you guessed it) brushed to raise its fibres, resulting in a luxuriously soft texture that feels great against the skin.
This shirt is perfect for layering, whether worn on its own, under a jacket, or over a lightweight tee.
Brushed cotton shirts are also versatile – casual enough for weekends but more than qualified for a 9-5 number, too. That combination of style and comfort also makes them a great choice for those looking to stay cosy while maintaining a fashionable edge during fall. Pair one with jeans or chinos, and you’ll have a reliable go-to for brisk autumn coffee runs.
Wool Overshirt
Tailor Store
It’s about insulation with a wool overshirt, but it’s not just about insulation. A sophisticated and practical layering piece for fall, it bridges the gap between a shirt and a padded jacket.
Heavier wool fabrics keep you warm while still being breathable, making them perfect for countryside walks or frosty school runs. The thicker construction and button-up design allows it to be worn as outerwear during milder days or as a mid-layer when the temperature drops further.
Look for muted, earthy tones like charcoal, navy, and olive, which will suit casual and semi-formal outfits well. Pair it with a crisp Oxford shirt underneath for a polished look, or layer it over a tee for something more relaxed.
Plaid Shirt
Taylor Stitch
A plaid shirt is a fall icon. That much-loved checked pattern, often in warm autumnal colours like red, green, and navy, brings a casual but eye-catching element to your fit. These shirts usually come in a soft, mid-weight fabric ideal for layering – wear it over a plain tee for a laid-back look or under a jacket for extra warmth.
For a sharper silhouette, opt for a more fitted style, or go oversized for a relaxed, rugged vibe. It’ll pair with jeans, chinos, combat trousers, or smarter pants in wool or corduroy.
Yes, everyone wears them, but that’s because they are consistently, endlessly stylish.
Chore Coat
Todd Snyder
When is a chore coat a jacket, and when is it an overshirt? The lines have blurred in recent years as this functional piece of workwear laboured its way into practically every man’s wardrobe. In cotton twill, canvas, denim or other lighter-weight materials, we’d argue it works best styled as a shirt, worn open or buttoned up over a simple T-shirt.
The natural instinct is to wear a chore coat with other workwear staples like denim or carpenter pants, but it’s also fun to cross the streams and pair one with smarter trousers. Either way, it’s a must-have for fall, no matter how the autumn winds blow.
Chambray Shirt
Todd Snyder
Chambray shirts are often mistaken for denim, but they offer a lighter, softer alternative that’s perfect for fall layering. Chambray fabric is woven from cotton, giving it a smooth finish that’s breathable and comfortable against the skin. Its lighter weight makes it ideal for transitional weather, whether worn solo or layered under a jacket.
The soft, washed-out look of chambray shirts complements autumn’s natural tones, and it also chimes with the preppy back-to-school vibe that still influences a lot of fall menswear.
The shirt’s laid-back, refined aesthetic means you can dress it up with chinos and a blazer or dressed down with jeans and boots. It’s the perfect choice for anyone who wants the rugged appeal of denim but with a softer, more refined feel.
Western Shirt
Velasca
Everyone has an Oxford shirt, everyone has a plaid shirt, everyone has an overshirt. Not everyone has a Western shirt. A bold, distinctive option that adds character to your fall fashion, this cowboy classic falls somewhere between very rugged and very dandy.
Known for their pointed yokes, snap buttons, and often detailed stitching, Western shirts are typically crafted from durable fabrics like denim or chambray.
These shirts are ideal for adding some yee-haw to your everyday style, unapologetically embracing classic Americana. Pair it with dark jeans or tailored pants and add a wool jacket or cardigan over the top if you need another layer. Unless you want to look like Woody from Toy Story, leave the cowboy boots to the rodeo riders.
