Every year, around the same time the first proper cool week rolls in, I do my seasonal wardrobe edit. This time the radar picked up something I keep seeing on the street: guys still in open-toed sandals and resort shirts while the fallen leaves are on the ground. It’s not that any single item is bad — it’s that some pieces belong to a different season, and wearing them out of context is the difference between “effortless” and “forgotten in the bedroom.”
I’ve spent six years forecasting trends, and seasonality is the signal most people ignore. Some items are trans-seasonal heroes — an overshirt, mid-wash jeans. Others only work when the sun is overhead. Here’s the list of things I’d stop wearing once summer ends, and what I’d swap in instead. I’m doing the edit for the men in my life, so read this as their radar.
1. Flip-flops
They’re trending, and that’s exactly the trap. A trend doesn’t stretch across two seasons. Unless he’s jetting off for some autumn sun, the flip-flop goes in the box now — next June at the earliest. If he insists on a sandal, make it closed-toe and pair it with socks: think a Boston-style clog or something in that relaxed family. It keeps the ease, drops the beach.
2. Short shorts
Hemlines have been creeping up all summer, and a few men refuse to let go of the 5-inch inseam. If he has the legs, more power to him — as long as he also has the sense to know when to stop. If it’s too cold for short shorts, it’s usually too cold for shorts altogether. The freedom of bare legs can survive in a wide-leg or relaxed trouser: snug at the waist, plenty of room through the leg. He keeps the movement, gains the warmth.
3. Vacation shirts
Nothing says summer like a breezy camp-collar shirt splashed with palm trees or a bright abstract print. Which is exactly why it starts to look questionable once the sun isn’t a permanent feature. A plain heavyweight version might squeeze out a few more wears — but anything that looks like it belongs next to a swimming pool with a piña colada should be retired until next year. Swap in an Oxford shirt, a knitted polo, or a brushed-cotton button-down. Same role, far more seasonal. Or lean fully into autumn with a heavier overshirt in corduroy, wool, or substantial cotton twill.
4. Madras anything
Madras is almost inseparable from summer: lightweight, colourful, bright checks. Perfect with shorts and loafers on a warm July evening. Try the same thing on a grey October morning and you look a little unhinged. That doesn’t mean checks are off the table — autumn is arguably when they come into their own. The fabric and colour just need to change. Trade the lightweight madras for brushed flannel, wool, or heavier cotton. And swap the sun-faded pink, turquoise, and yellow for navy, forest green, burgundy, and brown. Same pattern, deeper palette.
5. Espadrilles
Few shoes are better suited to hot weather — lightweight, breathable, easy. But a woven jute sole and a wet pavement are not friends. Once the weather turns, they’re out. The swap should keep the same relaxed feel with more substance: a penny loafer keeps that laid-back character and works far better with autumnal fabrics. Or a simple suede sneaker or desert boot — easy-going for everyday, but built for the months ahead.
6. Traditional deck shoes
The deck shoe’s grippy sole was designed for traction on wet yacht decks in blazing sunshine — not pavements in pouring rain. If he likes the silhouette, there’s a fix: take the same basic upper and put it on a much more substantial commando-style sole, the way Timberland’s 3-Eye Lug or Paraboot’s Brian do it. A little extra distance between the foot and wet ground, and it suddenly feels right for autumn and winter.
7. Linen legwear
The same breathability that makes linen a heat-battling wonder leaves it ill-equipped for cooler weather — and heaven forbid it should meet any rain. If he likes the texture linen offers, there are far better fabrics for autumn: corduroy, twill, duck canvas, cotton drill, wool. None of them will reveal his underwear to the world when they inevitably get sodden.
8. No socks
There’s a time and a place to free the ankle. Outside of summer, it’s not it. Whether he’s getting suited up for a wedding or just throwing on casual clothes for the weekend, a pair of socks should be part of the ensemble. Socks aren’t the enemy — they keep ankles shielded from the autumn cold, and they’re a quiet way to add character. Not novelty, not jokey. Subtle: flecked wool, a bold block colour, or a simple pop of black or white for contrast.
9. Summer fragrances
Fragrance has seasonality too. The zingy citrus, marine, and ultra-fresh scents that work brilliantly in warm weather can feel thin once the cold sets in. That bottle built around bergamot, neroli, and salty sea air isn’t doing much for anyone wrapped in wool on a cold, dark evening. Reach for something with more depth and warmth: woody, spicy, resinous, amber-heavy scents sit naturally with autumn clothes and cooler temperatures. Cedar, vetiver, tobacco, leather, incense. He doesn’t need overpowering — just a scent with a little more oomph behind it.
10. Crochet shirts
Crochet shirts have been a fixture of summer menswear for the past few years, and for good reason: breathable, tactile, a bit of visual interest on 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 texture is what he’s after, autumn has better options. Swap crochet for chunky knits, waffle-knit cotton, brushed wool, or a good cable-knit sweater. Same surface interest, in a form that makes more sense when the temperature drops.
Trend Signal
The quiet signal this season: texture is doing the work colour used to do. The men who look intentional in autumn aren’t the ones wearing louder — they’re the ones swapping light, open fabrics for brushed flannel, waffle knit, corduroy. Same silhouette, more substance. That’s the edit worth doing before the first real cold week.
Do I really have to put all of this away until next summer?
Most of it, yes. The exceptions are the plain, heavyweight versions — a solid camp-collar shirt or a plain linen piece can squeeze out a few extra wears if the autumn stays mild. But printed, light, open-weave items belong in the box.
What about a guy who lives somewhere with a mild climate?
Then the timeline shifts. The rule isn’t the calendar — it’s the weather. If it’s warm enough that a linen trouser still makes sense, keep wearing it. The moment it stops making sense, it goes in the box.
Where do I start if the wardrobe is a mess?
Start with the feet. Shoes are the most visible season-marker — swap the espadrilles, deck shoes, and flip-flops first, and the whole outfit reads as more seasonal even before the rest of the edit is done.
A note from Sophie: I’ve been guilty of the same thing — wearing a summer piece one month too long because it was comfortable and I wasn’t ready to say goodbye. The edit is easier when you do it in one sitting, with a box and a list. The wardrobe feels lighter, and so do they.
Worth it? Worth the box. Stay on the signal. — Sophie