Fall shopping advice from the homies
We asked our friends what they're wearing right now, and they delivered.
Now that the autumn breeze has finally arrived (that is entirely contextual btw) and leaves are crunching beneath your trusty Vibram-soled boots (if you live in Florida, just indulge us), it’s that time of year when we all start eyeing our cozy, moth-nibbled sweaters, scuffed boots, and overbuilt jackets.
We’ve already been dropping our usual seasonal fall shopping guides like trousers, socks, and knitwear, with a few more fire-packed ones locked and loaded in the canon.
And while we consider it our job to both put you on to semi-obscure (and beloved) brands, at the end of the day, we exist for the community.
Which means spotlighting what people in our circles are wearing.
We started this series titled What the Homies Are Wearing to do just that. It’s become one of our ways to share good, personal style, and the lineups keep getting better.
We’ve tapped brand insiders, stylists, and all-around enthusiasts to share what they’re most hyped to pull out this season (plus a few new pieces they’ve got their eyes on).
This is part one. Keep an eye on your inbox for part two, dropping soon.
Rose Anderson — New York, NY
Head of Brand at Alex Mill, and writer of The Rose Period on Substack
What’s the one item you’re most excited to wear this fall?
OK, this is easy—I just got thise new Alex Mill trench, and it’s hardly come off my body since. I’ve never gotten so many compliments from strangers.
How would you describe your go-to cold-weather look?
Layered—with a color palette that goes together. I just came back from a week in Paris, where I (successfully) packed a carry-on and wore the same two pants, three tops, three sweaters, and one coat for seven days.
Rotating them equaled endless combos.
Also, don’t underestimate the power of an accessory—I love adding a pop of silver with Lié rings from Amalie and Cecilie Moosgaard, Jenny Bird earrings, or a signet ring from Kelsey Lim’s Abel Objects.
What does your footwear rotation look like once the season changes?
I usually wear ballet flats year-round—I just caved on silver metallic Repettos in Paris, but I love my Yuni Buffa’s (handmade in Italy) or Porselli’s (so hard to find, but Alex Mill sells them—get the red!).
As soon as the first cold-ish day hits, I’m pulling out a boot. My friend Kate Snyder just influenced me on these Loeffler Randall beauties—it’s so hard to find that perfect espresso brown color, and these ones are—God help us—perfect!
Any must-have jackets you recommend for layering in the fall?
If I’m not wearing the trench coat, I’m in my Doen Pascual jacket—the proportions are to die for, and I love the cord lining. My butter-yellow one is out of stock, but the chestnut brown goes with everything too.
Are there any new pieces or trends catching your eye this season?
I snagged a few vintage rugby shirts via my friend Nora of Thanks, It’s From eBay, and they’ve become part of my fall uniform. This Loeffler Randall rugby is equally fab.
Also (obviously a little bias here), but the Alex Mill monogrammed tote is pretty much the only work and weekend bag you need. The monograms are hand-painted by Brooklyn artists—a great gift, too.
Do you follow any personal style do’s or don’ts for fall dressing?
Do: Always bring a sweater.
Don’t: Overthink it. Georgia O’Keeffe kept her closet almost entirely black and white so she could focus on her paintings, not her outfits. I love that—it’s my FA25 energy.
Chris Patrick Curran — Richmond, VA
Menswear Enthusiast
What’s the one item you’re most excited to wear this fall?
I have an Engineered Garments G8 jacket I bought a few years ago in a heavyweight ripstop fabric. It’s the perfect jacket. It has a satin quilted lining and side-tab adjusters that make it ideal whether I want to wear it on its own or layered over a hoodie or sweater.
My favorite detail is the hardware—it drives me crazy how brands will make a heavy-duty jacket with delicate zippers—but not EG!
The front and sleeve zippers are thick and super durable.
How would you describe your go-to cold-weather look?
I’m a denimhead at heart! I’ll always go back to a pair of jeans and a denim jacket. I like to wear my Kapital 1st Type Century denim jacket with my Heritage Fit Kojima jeans from Shockoe Atelier (a local denim factory I can walk to from my house). Paired with a pair of boots or the new EG x Vans slip-ons, and I’m set.
Besides that, I got a J.Crew cashmere V-neck sweater for Christmas last year, and I love how easy it is to just throw on and go.
What does your footwear rotation look like once the season changes?
My cold-weather footwear rotation is all about my leather shoes. I’m out walking my dog every day regardless of the weather, so my Red Wings and Hokas become my daily drivers.
I get sick of sneakers after wearing them all summer, but if I want something lower-profile and comfortable, I’ll alternate between my San Antonio Shoemakers Bout Time sneakers and my Aurora Middle English shoes.
Have any must-have jackets you recommend for layering in the fall?
The first expensive piece of clothing I ever bought was a Barbour Bedale jacket, and I’ve reached for the Beaufort I traded it for more than any other jacket.
Nothing is more autumnal than that signature big corduroy collar. Even though it’s synonymous with preppy Ivy style, I love using it in more casual outfits. The hard-wearing waxed canvas makes it look just as good layered over a hoodie as it does an oxford cloth shirt.
If you’re looking for something a little different, I really love vintage N-1 Deck Jackets. They’re not cheap, but reproductions from Buzz Rickson or Iron Heart are grails of mine right now.
I have a waxed canvas jacket based on an N-1 from Peregrine that I really love.
Are there any new pieces or trends catching your eye this season?
I’m not sure if this counts as a trend, but I always stop in my tracks when people use heavy denim jackets as a midlayer. I’m like, “Wow, that’s cool!” Last year, I wore a vintage down vest over an old Ralph Lauren denim jacket, and it just worked.
This year, I think I’ll swap the vest for a heavy Cowichan sweater. Oh—and rugby shirts are coming back in a big way. The one I have from Columbiaknit is going to get a lot of wear this year.
Do you follow any personal style do’s or don’ts for fall dressing?
A big don’t is: don’t start shopping for colder weather until you’ve had time to pull your current fall wardrobe out of storage.
Save yourself the grief of realizing two weeks past the return window that you already have a green Shaggy Dog sweater in the back of your closet!
Jalil Johnson — New York, NY
Stylist and writer of Consider Yourself Cultured on Substack
What’s the one item you’re most excited to wear this fall?
My Tod’s gold Gommino driving shoes and my Barbour Bedale jacket. On one hand, I want to dress like a wise old Italian man; on the other, I want to look as if I spend part of the year in the English countryside.
How would you describe your go-to cold-weather look?
Lots of layers—JFK Jr. in the George years, Armani’s Images of Man, and ’80s prep filtered through John Hughes and The Big Chill.
What does your footwear rotation look like once the season changes?
My shoe rotation mostly stays the same from summer into fall, with only a few exceptions. The main difference is that I start wearing socks again.
Do you have any must-have jackets you recommend for layering in the fall, or new pieces / trends catching your eye this season?
I’ve really been into bombers lately, both in leather and suede, and I’m also obsessed with corduroy pants and have been collecting a fleet of them for fall.
Do you follow any personal style do’s or don’ts for fall dressing?
I think, in general, you should wear clothes that feel like you, but at the same time don’t be afraid to experiment. Making mistakes is part of the journey.
Christina Elliott — London, UK
Stylist and Creative at Drake’s
What’s the one item you’re most excited to wear this fall?
This suede vintage trench I bought a few months back, but haven’t really had the chance to slip into yet! It’s great—very simple in detail, which makes it all the better. It has an almost mock collar, which stands up but is slightly rolled from the previous owner pressing it down.
It’s both buttoned and tied at the waist, but with no belt loops, so it’s easy to wear without the tie and avoids any unnecessary loops hanging around.
The pockets have a decent depth—perfect for my hands and belongings—as I’m still deciding whether or not I’m a bag girl.
How would you describe your go-to cold-weather look?
Most of the year, I don’t really deviate from a tonal look—often ecru, blue, grey, or black.
My go-to outfit probably revolves around a wide-leg trouser, either denim or cotton, with a silk cami tucked in and a cotton shirt of some sort worn over it. I’ll usually tie a piece of knitwear around my waist to give some shape to what would otherwise be an oversized look.
Almost certainly, I’ll be in a black pair of shoes and my traditional Austrian Appenzeller belt—for some interest and a pop of red.
I’ll finish with one of my many trench coats, likely Drake’s, as the raglan sleeve works amazingly with layers underneath.
What does your footwear rotation look like once the season changes?
I’m still trying to break them in after a few seasons of light wear, but I can’t wait to get my Celine Gardiane Western boots in suede back into rotation. I was trying to keep them away from the rain, but I have realized, like anything, they’re only going to get better once they’ve lived a little.
I saw a lovely before-and-after image of a similar pair from La Botte Gardiane, which made me realize I just need to commit.
After a day of breaking those in, I might need some respite in the form of a mule—either a black leather pair from Lemaire or an umber suede pair from Kunsten, an amazing Danish brand bringing style and comfort to wooden clogs.
And for something slightly more delicate, my prized vintage Chanel two-tone ballet flats in white and black, which I get very excited to wear.
Got any must-have jackets you recommend for layering in the fall?
Suede is great for fall—the chocolate suede chore jacket from Drake’s must be the perfect layering piece with lighter knitwear or a flannel shirt.
I’m also addicted to my Róhe Mandarin double-faced wool jacket in off-white; it’s simple, beautifully detailed, and its unstructured nature gives it great shape and movement.
Are there any new pieces or trends catching your eye this season?
I’ve always resonated slightly with the Western style—being a country girl at heart. I’m in need of both a practical and beautiful jacket; something like the Loro Piana black horsey jacket with a contrasting brown leather collar would be perfect.
It’s ideal for all weather, and looks just as good over a suit as it does with jeans and knitwear.
Do you follow any personal style do’s or don’ts for fall dressing?
Not really—I just dress how I feel, which is why I find packing for trips insanely difficult. How does one know what they might want to wear next week?
Just don’t be cold! Layering is key, both for creating an interesting ensemble and because I’m forever freezing.
A Shetland tied around the waist not only adds shape and textural contrast, but also comes in handy when the temperature takes a turn.
eBay rugby shirts and Rose forever 🫶