One day the sun shines bright, and a T-shirt seems to be enough, the next the air has a bite to it, and you wish you’d layered up. The transitional stretch of the calendar is once again here, and it calls for one thing above all else: the right jacket.
But what makes a jacket good for this season? It has to be versatile enough to pair with all your different outfits, light enough for warmer afternoons, and adaptable enough for evenings when the weather cools down once again.
It may sound like a mission impossible, but worry not, it isn’t. And no, you don’t need a whole wardrobe full of jackets. Just a few quality pieces will see you through the season and year after year.
Below, you’ll meet the top five men’s jackets that can bridge the gap between summer and autumn with effortless cool.
The Chore
The chore, or French work jacket, was originally designed in 1800s France as a tough, utilitarian layer for labourers: craftsmen, factory workers, rail workers, and farmers. Now, it’s one of the most wearable jackets you can own.
Cut from sturdy cotton canvas or denim, the chore jacket is recognised by its three or four large patch pockets and straight, slightly boxy fit. It’s ideal for layering over T-shirts in September and even over a chunky knit as the weeks grow colder in October.
And it doesn’t stop there. What makes it so effective as a transitional piece is its weight. It’s a very light alternative with just enough coverage without causing you to overheat. The rugged fabric can also withstand autumn showers and breezes, particularly if you opt for a waxed version.
When it comes to style, this is a flexible option that looks good in chinos, boots, jeans, and trainers. If you’re a fan of the modern, smart-casual look, try it in a neutral shade like navy, olive, or stone. And if you like a bold look, go for heritage indigo denim or corduroy.
But whatever you choose, you can trust it’s a jacket that only gets better with wear.
The Harrington
Nothing is as quintessentially transitional, cool, and timeless as the Harrington jacket. Lightweight, short in length, and stylish without even trying, it’s been a favourite staple since the 1950s. The neat collar, the elasticated cuffs, and the subtle tartan lining it often comes with strike the perfect balance between casual and sharp and do it better than almost any other jacket. It is a true icon of British craftsmanship.
The Harrington’s cropped cut is what also makes it perfect for the warmer end of autumn. That time when you want a layer that won’t weigh you down. At the same time, you can trust it to be smart enough to throw on over a shirt if you’re heading somewhere that calls for polish but not extreme formality. Think of the Harrington as the jacket that will work perfectly well for a weekend stroll, as it does for a dinner date.
If the weight and style are not enough, trust the heritage. This jacket was worn by everyone from Steve McQueen to the elite members of the Mod movement. It’s timeless and cool, so you won’t regret investing in it. Pair it with slim jeans, loafers, and a classic white tee.
Is that James Dean we’re seeing?
The Bomber
The Bomber was originally made for high-altitude missions during World War II, but it has enjoyed relevance on the ground ever since. Mainly thanks to James Bond himself. Just like the Harrington, its cropped length will do wonders for your legs.
The classic version comes with ribbed cuffs, a zip front, and a waist-length cut. And because of its lightweight nylon, it’s ideal for late summer evenings when you need just a touch of warmth. Switch to padded or wool versions when autumn’s bite sharpens, and you’ll be set even for the winter.
The Bomber is also particularly good if your personal style leans casual. It has that sporty, youthful energy that works with streetwear staples like trainers, hoodies, and slim trousers. However, it can still be styled in a more refined way. A sleek black bomber over a rollneck and tailored trousers for an easy way to smarten things up without losing your edge.
The Trench
Another diehard classic, the trench is simply unbeatable for transitional weather. Thanks to its practicality and elegance, it has stood the test of time since World War I. It’s water-resistant, light enough for early autumn, and protective enough to keep you dry on those inevitable rainy days.
Then, it’s also versatile, and because of its tailored silhouette, it works beautifully over work attire. You can instantly pull together a suit or smart trousers. But don’t think that’s where it all ends. Oh no, it can be just as easily worn with denim and a knit for a more casual weekend look.
Either way, the trench is here to stay, and it will be the kind of piece that will serve you well for years, not just seasons.
The Fleece
Now, not every jacket needs to be super sleek and tailored. Sometimes comfort is key. And if that sounds like you, then the fleece is your go-to.
Lightweight, insulating, and soft, this is the one you can trust when the chill of autumn really sets in. And the layering potential here makes it a very strong candidate for your transitional outerwear collection. On milder days, it’s enough to use as a top layer over a tee, but as the season progresses, it will slip easily under a heavier coat without adding bulk!
And if you want to avoid leaning too much on the casual, pair it with slim trousers or dark denim, and you’re good to go!
A Transitional Jacket You Can Trust
You’ve just met our heroes, now it’s up to you to make the right call. But whatever you choose, you’ll know it covers every situation you’re likely to face in the fight against transitional weather. And because these five jackets have already stood the test of time, you can be certain they’ll carry you through many seasons to come.