10 Things Stylish Men Stop Wearing When Summer Ends

Understanding seasonality is an often-overlooked but absolutely crucial part of being well-dressed. There are certain pieces that can make an outfit in the summer but kill one in the autumn. They’re the exact opposite of those trans-seasonal heroes like overshirts and mid-wash jeans – garments that, when taken out of their intended seasonal context, feel awkward, clumsy and downright wrong.

Stylish men know where to draw the line, but it always surprises us how many guys we see clinging to inherently summery things such as open-toed footwear and resortwear when there are fallen leaves on the ground.

If you’re unsure which pieces should be stored away until next summer, we’re here to help. Here are the things to stop wearing once summer ends… and what to wear instead.

Flip-Flops

Yes, we know they’re trending, but that’s no excuse to continue wearing them into autumn. For the avoidance of doubt, flip-flops should be shelved until further notice unless you’re jetting off for some autumn sun. Put them away, and don’t think about them again until next June at the very earliest.

We’d encourage you to wear proper shoes at this point, but if you absolutely must go down the sandal route, choose a closed-toe option and pair it with socks. Think Birkenstock Bostons, Bedrock Mountain Clogs or something else along those lines.

Short Shorts

In the world of shorts, hemlines have been creeping south for some time now, but there are still those men who refuse to let go of the 5-inch inseam. More power to them if they have the thighs to pull it off… as long as they also have the sense to recognise when it’s time to switch back to something longer.

If it’s too cold for short shorts, the likelihood is that it’s too cold for shorts altogether. If you don’t want to lose the feeling of freedom that comes with having liberated legs, a wide-leg or relaxed-fit trouser could be a good option.

Look for something that fits snugly at the waist but has plenty of room through the leg for freedom of movement.

Vacation Shirts

Nothing says summer quite like a breezy camp-collar shirt splashed with palm trees, florals or some sort of colourful abstract print. But that’s exactly why they start to look increasingly questionable once the sun is no longer a permanent feature overhead. You might be able to squeeze some extra mileage out of a plain, heavyweight version, but anything that looks like it belongs next to a swimming pool with a piña colada should probably be retired until next year.

Swap it for something with a bit more substance. An Oxford shirt, knitted polo or brushed-cotton button-down will fulfil much the same role while feeling far more appropriate for the season. Alternatively, lean into autumn with a heavier overshirt in corduroy, wool or substantial cotton twill.

Madras Anything

Madras is one of those fabrics that’s almost inseparable from summer. Lightweight, colourful and usually rendered in some combination of bright checks, it’s perfect with shorts and loafers on a warm July evening. Try wearing the same thing on a grey October morning and you will look vaguely unhinged.

That doesn’t mean checks are off the table altogether. Quite the opposite if you ask us. Autumn is arguably when they come into their own, but the fabrics and colours need to change. Swap lightweight madras for brushed flannel, wool or heavier cotton, and trade those bright, sun-faded shades for something deeper and richer. Think navy, forest green, burgundy and brown rather than pink, turquoise and yellow.

Espadrilles

Espadrilles are a bit of a divisive topic, but it’s hard to deny that there are few shoes better suited to hot weather. They’re lightweight, breathable, comfortable and, depending on who you ask, look great with everything from swim shorts to linen trousers. Unfortunately, those same qualities make them completely useless when the weather turns. A woven jute sole and wet British pavement are not natural bedfellows.

This is the point to swap them for something similarly relaxed but considerably more substantial. A penny loafer is an obvious choice, retaining some of the espadrille’s laid-back character while working far better with autumnal fabrics and trousers. Alternatively, try a simple suede sneaker or desert boot – both easy-going enough for everyday wear, but infinitely better equipped for the months ahead.

Traditional Deck Shoes

Another shoe that struggles to cope with anything other than summer weather is the deck shoe. Its flat, grippy sole may have been designed for traction on wet surfaces, but we’re talking yacht decks in blazing sunshine as opposed to pavements in the pouring rain.

The good news is that there is an alternative for those who like the silhouette. Shoes such as Timberland’s 3-Eye Lug and Paraboot’s Brian take the same basic upper and place it atop a much more substantial commando sole unit. This transforms it into something that feels far more suitable for autumn and winter, all by putting a little extra distance between wearer and wet ground.

Linen Legwear

That same breathability and airiness that make linen such a wonder fabric when it comes to battling the heat leave it ill-equipped to deal with cooler weather, and, heaven forbid, it should see any rain.

If you like the element of texture it offers, there are far better-suited options out there to see you through the autumn. Think corduroy, twill, duck canvas, cotton drill and wool for starters, none of which will reveal your underwear to the world when they inevitably get sodden.

No Socks

There’s a time and a place to free the ankle, and anywhere outside of summer is not it. Whether you’re getting suited up for a friend’s wedding or just throwing your casual clothes on for the weekend, make sure a pair of socks is part of the ensemble.

Socks are not the enemy. Not only will they keep your ankles shielded from the autumn cold, but they can be used to add some character to an outfit. Not in a novelty, jokey sort of way, but in a subtle manner. Think flecked wool, bold block colours or even just a simple pop of black or white for contrast.

Summer Fragrances

Fragrance has seasonality too, and the zingy citrus, marine and ultra-fresh scents that work brilliantly in warm weather can feel a little thin once the cold sets in. That bottle built around bergamot, neroli and salty sea air probably isn’t doing much for you when you’re wrapped in wool and heading out into a cold, dark evening.

This is the point to reach for something with more depth and warmth. Woody, spicy, resinous and amber-heavy fragrances tend to sit much more naturally alongside autumn clothes and cooler temperatures. Notes like cedar, vetiver, tobacco, leather and incense all work well. You don’t necessarily need something overpowering, just a scent with a little more oomph behind it.

Crochet Shirts

Crochet shirts have become a fixture of summer menswear over the past few years, and for good reason. They’re breathable, tactile and lend a bit of visual interest to otherwise simple warm-weather outfits. The problem is that all those little holes become considerably less appealing once there’s a chill in the air.

If it’s texture you’re after, autumn has plenty of better options. Swap crochet for chunky knits, waffle-knit cotton, brushed wool or even a good old-fashioned cable-knit sweater. You’ll get the same sort of surface interest, but in a form that makes a bit more sense when the temperature drops.

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