9 Summer-to-Fall Style Swaps Every Man Should Make

Transitioning from fall/winter to spring/summer is pretty straightforward. Warmer weather means fewer types of garments, which, although creatively stifling, removes a lot of the head-scratching when it comes to piecing outfits together. Moving in the opposite direction can be a little trickier.

All of a sudden, your wardrobe options multiply. Shorts and camp-collar shirts won’t cut it anymore – now you have to think about curating layered looks that will keep you comfortable in the cooler weather and look good at the same time. This can be daunting initially, but as is always the case, we find that making a few easy wardrobe substitutions is the best way to ease yourself back in.

So, what should you be swapping for what? Well, we have a few suggestions. From ditching light-wash denim in favour of darker hues to retiring linen and incorporating heavier fabrics, here are the summer-to-fall switch-ups we think you should make.

Swap Your: Light Jacket

Todd Snyder

Light outerwear does have a place in fall wardrobes, but mostly as a layering tool. With the temperature dropping, you’ll need more insulation to stay warm, and most simple overshirts and windbreakers underdeliver in this area.

What you want is something that feels like a warm hug when you put it on, and a big fleece jacket does exactly that.

For A: High-Pile Fleece

The woollier and more heavily textured the better. You want something that’s really going to trap your body heat while bringing a tactile element and some visual interest to your outfits at the same time.

Patagonia’s Retro-X jackets are a bit of a benchmark in this department, but you can find cheaper alternatives on the high street or at your local thrift store.

Swap Your: Linen Shirt

Velasca

Linen is a miracle fabric when it comes to surviving in the blistering summer heat, but its practicality has limits. With the mercury dropping, that breathability and lightness that’s so highly prized in summer becomes a fundamental flaw.

At this time of year, you’re trying to warm up, not cool down.

For A: Heavyweight Flannel

In addition to a few well-fitting Oxford shirts, a heavyweight flannel is something you’ll definitely want in your corner when the weather starts to turn. The brushed cotton fabric is an excellent insulator, and going for a nice bright colour is a simple way to bring autumn outfits to life.

A classic buffalo check in red and black is always a good option, but try to avoid going full lumberjack fancy dress.

Swap Your: Lightweight T-Shirt

Luca Faloni

In the heat of the summer, a T-shirt’s job is to keep you cool. It needs to be light, relatively thin and breathable. But those properties that make a tee great for the warm weather become negatives when the leaves start to fall.

For A: Heavyweight Long-Sleeve

You still need a solid base layer upon which to build your outfits, but it should be thicker, heavier and with more structure to reflect the cooler weather.

A long-sleeve T-shirt in heavyweight cotton is the perfect option. Every bit as simple and versatile as its lightweight short-sleeve counterpart, but a bit more seasonally appropriate.

Swap Your: Linen Shorts

Luca Faloni

It doesn’t get much comfier than a pair of linen shorts. They’re so light, airy and soft that it almost feels like you’re wearing nothing at all.

Unfortunately, they’re not exactly built for anything other than hot, sunny weather.

For Some: Drawstring Pants

Thankfully, there exists a legwear option that comes close to matching the comfort of linen shorts in a more autumn-friendly cut: drawstring pants.

Just make sure to go for a nice relaxed fit and a slightly thicker fabric. Cotton twill and corduroy are both solid choices.

Swap Your: Light-Wash Jeans

Wax London

If you’ve been rocking jeans during the summer months, chances are they’re of the light-wash variety. Dark denim can feel heavy and stifling in the hot weather, but as the nights draw in, it becomes the default setting once again.

For Some: Raw Denim

This is the perfect time to start working on your fades again. Get the heavy stuff out and wear it to death while it’s cold enough to do so.

Swap Your: Leather Sandals

Todd Snyder

Regardless of season, there should always be some goes-with-everything leather footwear in the mix. During the summer, a pair of leather sandals fits the bill, but you’re probably going to want to retire the Birkenstocks before there’s frost on the ground.

For Some: Chunky Derbies

A pair of chunky Derby shoes is our weapon of choice this year. Think something a little bit different – anything that veers away from the traditional round-toe design without going too weird is ideal.

Paraboot’s iconic Michael moc-toe Derby is a great example. Super versatile and seasonally appropriate without being boring.

Swap Your: Suede Loafers

Velasca

Likewise, soft suede shoes that can flit seamlessly between smart and casual are a must no matter the time of year. The important part is that the specific shape of the shoe works for the weather.

This isn’t to say you can’t wear loafers outside of summer, but footwear that offers more coverage is generally better suited for colder weather.

For Some: Soft Suede Chukka Boots

Like loafers, a pair of suede chukka boots is comfortable, relaxed and versatile enough to mix with everything from jeans to tailored jackets.

Clarks is one of the best brands in this department with classic styles such as the Wallabee boot and the Desert boot that are pretty hard to beat.

Swap Your: Linen Cap

Luca Faloni

It’s not full beanie season just yet, but you’d be well advised to have something a bit more substantial than a lightweight linen cap to put a finishing touch to your fall fits.

For A: Corduroy Alternative

Corduroy is the perfect substitute here. Slightly warmer and thicker, with some texture to add another layer of visual interest. Go for something in a nice rich autumnal shade like burnt orange or maroon.

Swap Your: Summer Fragrance

Floris

The light and fresh fragrances that work so well in the summer can get lost in cooler air. This is where it pays to switch to something deeper and richer.

For: Something Heavier

Forget about zesty and floral scents and focus on heavier, more robust options.

Think leathery and smoky, with base notes of oud and sandalwood. These types of fragrances tend to have much better sillage and will hold their own in the cold much more effectively.