A Week in Outfits

What I'm wearing ATM.

Hi friends! Ahhh October, you glorious witch. After an Indian Summer overstayed its welcome in my neck of the woods, the weather is finally feeling like fall and it’s nothing short of spectacular. The babies (OK, they are four and a half and three years old, but I’ll never stop referring to them as such!) are miraculously sleeping until 7:30 every morning, which feels like a cosmic reward before daylight savings ruins everything next weekend. And curling up under a blanket with a glass of wine and a good TV show has never felt better.

As a Minnesotan, fall is basically my Super Bowl of style. That glorious (albeit short) stretch between sweating through your t-shirt and freezing through a parka, and I’m out here layering like it’s a competitive sport. The air just hits different, and getting dressed is inspiring again as I pull for my favorites—knits, lightweight toppers, denim, suede, leather—to create layered looks.

Ahead, I’m sharing a few fall outfit formulas I’ve been loving lately. While I’m sharing some of my favorite tries and buys as of late, also think of this as a nudge to remix what’s already in your closet—sometimes we just need a little spark to restyle what we already own instead of buying new. Xx

Cos sweater; Everlane clogs; Levi’s jeans, perfectwhitetee t-shirt

1. Call me a broken record, but I cannot shut up about this cashmere crew from COS. The quality? Unreal. The fit? That perfect mix of boxy and cool—the kind that makes you look effortlessly put-together even when you’re just wearing jeans, a sweater, and a white tee. Already scheming my next color…navy, maybe? And yes, I’m milking my Everlane suede clogs for all they’re worth before winter rolls in and ankle-baring becomes a distant memory.

Alex Eagle x J.Crew jacket; Levi’s jeans; The Great long sleeve t-shirt; Freda Salvador loafers (code Madeline10)

2. The Great’s Long Sleeve Crop Tee is peak layering perfection. Buttery soft, perfectly boxy, and thin enough to layer under all your sweaters and jackets. Speaking of jackets, I fell hard for the Alex Eagle x J.Crew collab and wasted exactly zero time making that mohair varsity bomber mine. (I sized up to a medium for a looser, cooler fit). Tip: Etsy, vintage, and resale stores and sites have absolutely killer varsity bomber options. Don’t sleep on secondhand!

Levi’s trousers; old burgundy Marion Parke boots (almost identical pair here in black, and other burgundy pairs here, here, here, and here); Aritzia bomber; Jenny Bird earrings; Coach suede bag

3. I’m deep in my red wine era, and by that I mean I can’t stop buying clothes in every shade of oxblood, merlot, and cabernet. Case in point: I loved my Aritzia Synergy bomber in black so much that I had to grab the burgundy too. Styled with my burgundy boots from Marion Parke for a tonal moment. And, please, let me vouch for these Levi’s—they’re not jeans, and not stiff trousers, but that sweet spot in between. 100% cotton, relaxed but somehow super flattering. So comfy you’ll forget to change into sweatpants.

Agolde jeans; Quince cashmere sweater; B-Low the Belt belt (look for less here and here); boots old Vagabond—similar here (Wally on sale!), here, and here; Warby Parker glasses; Jenny Bird hoops

4. Straight from the Bible according to Madeline: An all-black fit never misses. I’ve been on the hunt for a new black jean long enough for my legs (I’m 5’9”, for reference) and the tags on these AGOLDE high-waist stovepipe jeans didn’t stand a chance. I’m usually a AGOLDE 90s Pinch waist girl, but find those are better for summer. The stovepipe are next-level comfy with great stretch and a sleeker straight leg silhouette.

   Snakeskin has me in a chokehold this season, and this B-Low the Belt that slithered into my collection makes such a statement while adding a bit of edge and interest to a monochromatic look.

Old Aritzia effortless trousers (other colorways here and here, similar style here); Zara shoulder pad sweater; Tony Bianco suede loafers; heaven mayhem earrings

5. After doing a quick audit of my fall shoe stash, I realized I was missing one thing: a suede loafer. These Tony Bianco espresso beauties are basically fall packaged into a shoe. I’m obsessed with the classic penny-strap-inspired vamp and that subtle scrunch detail that keeps them from looking stiff.

   Also, consider this my official PSA: Aritzia’s Effortless Pants are life-changing. Give your jeans a well-deserved day off. With multiple colors and fabrics, they move with you, feel absurdly comfortable, and somehow drape like you spent way more than you did.

Agolde denim jacket (sold out most places—similar cinched style by Good American, Gap, and GRLFRND); Agolde 90s pinch waist jeans; M.Gemi flats

6. One of my go-to outfit formulas for those mornings when I feel like I have nothing to wear—or literally have five minutes to get dressed? Denim on denim. The trick? Either go so matchy-matchy so the tones are basically twins, or swing the other way and embrace full-on contrast. And yes, M.Gemi’s Una flats live up to the hype. The square toe keeps them from veering into too-sweet ballet-flat territory, while still feeling polished and easy to throw on with everything.

Zara nylon bloomers; Alohas sneakers; Toteme bag; Free People sweater

7. After including these Zara pants in this week’s “Sunday Best” roundup, I had to show you them on. A nylon jogger is a cool, unexpected alternative to your leggings or sweats—perfect for off-duty weekend runaround days when you want to look chic without sacrificing comfort. Speaking of elevated essentials, these ALOHAS Club sneakers feel way more elevated than your average sneaker with the calf hair, suede detailing, and sleek shape.

Etsy bag; Ronny Kobo sweater; Citizens of Humanity jeans; old J.Crew boots (similar here, here, and here); Fabrique jacket; Aritzia belt

8. What you’re not seeing about this sweater hiding underneath the jacket— shoulder pads! V-necks are everywhere this season, and I love them styled alone or over a white tee. Call me a walking autumnal color stereotype, but olive green and brown? A match made in earth tone heaven.

Steve Madden boatshoes; Rails jeans; Quince sweater; B-Low the belt belt; Freja bag

9. Leopard print is making a major comeback this season, and a fierce jean offers a bold twist to your usual jeans-and-sweater combo. Mixing brown and black tones is totally on trend right now—both are neutrals, but pairing them together adds unexpected warmth and depth to any outfit.