I was scrolling Instagram last week, as you do, when I realised a lot of British menswear accounts had posted their autumn fits. Which I guess isn’t new or surprising. But something about seeing all these guys looking effortlessly put together in cool weather made me….envious?
Jealous might be too strong a word but you know what I mean? Not that I wish the weather was cooler in Chicago (thank god it isn’t), but guys across the pond seem to have autumn style dialed in a way Americans don’t. Is American style too obsessed with “wearability” in the autumn?
Are we overthinking it? Regardless of what the rest of us are doing, autumn is my favourite season to wear clothes.
After fighting with summer style for months (let’s be honest: for most of us it just consists of shorts and whatever t-shirt isn’t covered in pizza grease), autumn brings weather that’s comfortable but unpredictable enough to layer.
Boots suddenly make sense again. Jackets become essential but not overwhelming. It’s everything summer isn’t.
The main thing I noticed browsing all these British fits was that they really do have autumn figured out, and I have no doubt that theirnative guides a lot of that. Clothes built to handle fog and drizzle are going to perform way better when you’re going from 45-degree mornings to 65-degree afternoons. And those traditional fabrics – waxed cotton, heavyweight wool – were made to handle just about anything Mother Nature throws at you.
Two years ago I had a similar realization when I was struggling to put together a functional autumn wardrobe. I bought a bunch of random clothes that looked good online but didn’t really go together – a number of standalone pieces that felt great on their own but would never be in the same wardrobe at the same time. Then I saw an autumn lookbook from a British guy and it all came together: Jacket situation.
For years this was where I struggled most. Jackets that were too heavy for midday highs. Jackets that looked horrible with sleeves rolled up.
Jackets that weren’t waxed cotton because, well, they never seemed to quite work. Until I started paying attention to British guys…then it all clicked. Waxed cotton is basically magical.
You can layer it over anything, in any weather, and it always looks appropriate. Doesn’t feel too heavy for Chicago highs but still protects against wind and rain. Layered under a jumper on cool mornings, loose over a tee on nicer days.
Looks ridiculous with a suit, but who wears suits in this weather? So where do you start with jackets? Well, first off: stop worrying about Barbour .
I get it, Barbour = waxed cotton = British guy Autumn Essential. Problem is, Barbour jackets can be expensive and kind of…preachy? There’s a reason they try to push those influencers on you.
Wear a Barbour vest to class and you’re immediately shouted down by aggressively mustachioed hipsters yelling about “proper thread count”. Wear a waxed Barbour jacket and you run the risk of looking like you’re trying too hard, heading out to the countryside for a Sunday roast. I actually scored this vintage Barbour jacket at a Lincoln Park consignment shop for about $120.
Not cheap by any means, but well worn in and loved by the former owner enough that it had that broken-in look you can only get from years of adventure. He also rewaxed it himself about six months ago so the wax was still fresh and it held up dry throughout the autumn and winter. Works with a t-shirt on nicer days, looks great layered under a jumper when it gets cold.
Doesn’t scream BRITISH GUY LIKE I’M CONSTANTLY WORRIED ABOUT. Love it. That being said, there are plenty of excellent contemporary waxed jackets out there that don’t have the Barbour name attached to them.
Hell, I even picked up this super nice Flaine waxed jacket at TJ Maxx a few years ago and wear it all the damn time (it’s currently on sale!!). You just gotta find a jacket that fits your lifestyle, not the lifestyle you think you should be living and walking around the Yorkshire Dales. Overshirt game is strong too.
For years I wrote off overshirts as bullshit. Made expensive button-up shirts into “overshirts” so you can charge more. Kind of gimmicky?
But, uh, no? They actually fill a really nice gap between traditional button-ups and jackets. Got this awesome heavy cotton overshirt from Wool & Prince last year and I probably wear it at least 3 days a week all autumn and into winter.
Great over a t-shirt if it’s chilly out. Looks awesome layered under a jumper when it gets cold. Never looks too bulky or ridiculous when you throw it on over whatever else you’re wearing.
Speaking of jumpers: autumn is jumper season. What I realised I was missing from my wardrobe was colour. Grey and navy are my favourite jumper colours because “everything goes with grey and navy”.
Result? Everything I owned was greys and navies so I ended up looking…greys and navies all the time. Fal AF.
Thankfully I stumbled upon this awesome forest green merino crew neck jumper (Amazon link!) last year and it’s been a game changer. Sure, it was more than I usually like to spend on a jumper but it’s washed beautifully and gets softer with every wash. It goes with anything and doesn’t make me look boring like half my closet.
Cable knits are also big right now, and I’m not just talking about the classic cream ones. Got this bright mustard colour one last year and wasn’t sure what to make of it at first, but it’s been one of my most-worn pieces since. Somehow looks awesome with dark jeans/chinos.
Bright colours works wonders when you’re basically living in greys and navy all summer. This whole cardigan thing took me awhile to get on board with, honestly. Kind of had a “dad wearing jumpers while picking you up from football practise” vibe for the longest time.
But once I bit the bullet and got a chunky knit cardigan in a shawl collar…it all clicked. Layers so well under jackets. Doesn’t feel too bulky under jumpers.
Can easily be removed when you’re inside. Fuck it: own the dad jumper vibe. Last but not least: button-downs.
Oxford button-down shirts are basically the base layer you’ll build everything else on top of. Been through the struggle of trying to figure out button-downs myself for years. Stuffed shirts don’t work under jumpers.
Non-iron shirts aren’t breathable enough for active wear. Expensive shirts shouldn’t have to scrape chicken grease off after eating delivery…etc etc. What I learned the hard way is that you really do need to spend money on a good oxford shirt, but you don’t need to spend too much.
Button-down wise, I’m pretty hooked on the mid-tier range ($70-90) as offering the best versatility. Lots of options there that will serve you well all autumn and winter. Also don’t sleep on heavier t-shirts or henleys.
Barely wore any t-shirts in the autumn/winter before because they felt too thin. But when it’s 65 and sunny out? Thicker cotton t-shirts are perfect on their own.
Great under open shirts. Looks great under jumpers when it gets colder. Cheap ones can be found at places like Uniqlo and J Crew.
Last couple years I’ve really been digging heavyweight denim. All that thicker waxed/jacket stuff feels like it’d be overkill with regular summer-weight denim, but throw on your favourite pair of raw jeans in the autumn and winter and suddenly they make sense. Was constantly taking my raw Selvages off from May-August just because it was too hot to care about wear-in.
Come September they were my favourite thing to wear. Same goes for corduroy. Was intimidated by cords for the longest time because freshmen english teacheruite.
But when you find cords in the right shades they’re actually amazing for autumn. Got these olive cords last year and they’ve been great. Perfect with everything in my wardrobe.
Thick enough to give some visual interest but doesn’t feel too heavy weight-wise. Maybe my favourite discovery has been flannel trousers. Don’t really know how to describe the vibe they give off; somewhere between casual and dressy.
Not as dressy as wool trousers, obviously, but definitely feel more elevated than jeans or chinos. Throw them on with a jumper and you’ve got yourself a casual autumn look that doesn’t feel borrowed from your dad’s closet. Boot selection is huge this time of year.
Tried so many different styles for awhile – I fell in love with desert boots, went down the Chelsea boot rabbit hole for awhile. Even got heavy into dudes with work boots. All great styles to have in your autumn rotation.
Desert boots seem to be the most versatile option for every day wear. They’re easy to slip on. Go with jeans or chinos.
And are comfortable enough to walk around in all day. I usually stick to suede for the autumn because it can take getting wet better than leather. Chelsea boots are great for wetter days.
No fuss with laces if you’re rushing out the door. And handle puddles better than most other shoe styles. When it’s really messy out though?
Might as well just commit to something with waterproof seams. Got a pair of derby boots last year that can handle just about anything but rain. Heavier than my desert boots/chelseas but some days that’s exactly what you need.
Scarves. Don’t forget scarves. Honestly didn’t realise how much of a difference a scarf can make until I started paying attention to British guys.
Sure they’re functional, but they really do help pull an outfit together.
Got this simple wool scarf in dark green that matches almost everything in my jacket and jumper rotation. Beanies are a hit or miss game too.
Either you look like Robocop’s head is too big for his body or you actually find one that works with your face shape. Finally found one I liked last autumn and instantly became one of those guys who HATES taking his beanie off when someone takes their picture. Hope you found something helpful in all that.
What I’ve learned from living vicariously through Brits this autumn is that it doesn’t take fancy clothing to have a versatile wardrobe. All it takes is a bunch of stuff that works together. Layers you can add or remove at will.
Colours that fit the season. Basically, stuff that doesn’t completely suck when the weather can’t make up its mind whether it wants to be spring of autumn. Post photography at Howell Square last week when it was ninety degrees and I was rocking shorts and a t-shirt but felt awesome anyway because my core was covered.
Go figure.
