If I Saw You in Any One of These 7 Classic, Elegant Outfits This October, I'd Think You'd Hired a Stylist
From jumpers with leather trousers to bomber jackets with midi skirts, here's what to wear in October, according to a fashion editor.

Brittany Davy
The way I see it, October 1st marks the official beginning of the. autumn/winter season. While September still holds the promise of unexpected sunny days and a few final outings for our cotton dresses, October is when we collectively give in to the onset of chilly mornings and darker evenings and start to embrace the season's more enjoyable qualities.
At the top of my list? The fashion. Cosy knitwear, luxurious layers and rich, moody colour palettes are just a few of the things I've been secretly looking forward to wearing while everyone else mourned the end of warm-weather dressing. And post-equinox, it's high time we all started assembling these pieces into outfits we'll wear for the season ahead.
After trawling through more Instagram accounts than I'd care to admit, I've bookmarked seven key looks suitable for whatever weather the coming month might throw at us (but maybe keep a few extra layers and an umbrella on hand, just in case). Without further ado, this is what to wear in October.
What to Wear in October: 7 Stylish Outfits to Try Now
1. Jumper + Leather Trousers + Slingbacks
Style Notes: Leather is having a moment in both the trouser and bag departments, especially in classic autumnal hues like black and chocolate brown. Invest in a quality pair of trousers like Danielle's and complete the easy October look with a cosy knit and sleek slingbacks.
Shop the Look:
2. Knit Dress + Suede Bag + Chelsea Boots
Style Notes: If you're going to invest in one item this month, make it a quality knit dress in a classic colour. Not only will this versatile staple carry you into the colder months in style, but it will serve you for many seasons to come as it's the very definition of anti-trend.
Shop the Look:
3. Bomber Jacker + Trousers + Ballet Flats
Style Notes: Bomber jackets will forever have a place in my wardrobe, pairing well with dresses, jeans and trousers alike. This season, I'll be taking a cue from Alexis (pictured above) and mixing up my black and brown hues for an intentional look.
Shop the Look:
4. Relaxed Blazer + Midi Skirt + Low Heels
Style Notes: However you feel about pencil skirts, there's no denying how incredibly chic this outfit is—especially with the mix of black and grey making it feel doubly elegant. This is an outfit that you can wear in or out of the office this season.
Shop the Look:
5. Cropped Jacket + Leather Shorts + Tonal Accessories
Style Notes: Cooler weather brings with it the opportunity to don one of the most effortlessly stylish wardrobe staples: the knitted dress. Anouk offers up a masterclass in matching your accessories to your outfit, and I'm loving her choice of olive green.
Shop the Look:
6. Wool Coat + Flannel Shirt + Jeans
Style Notes: A wool coat is a cold-weather classic. To make it feel '2025', pair it with a trending check flannel shirt and some loose-fit jeans.
Shop the Look:
7. Faux-Fur Collar Jacket + Pleated Skirt + Mules
Style Notes: When in doubt, I always bring it back to a monochrome look.
Shop the Look:
Bébhinn Campbell is an Edinburgh-based fashion and lifestyle writer and editor. She started her first blog at age 14 and went on to intern at publications in Berlin and London, including Dazed & Confused and Indie magazine.
A job at a fashion startup took Bébhinn from Ireland to Scotland in 2019, where she now works as a freelance journalist and copywriter covering everything from travel and interiors to styling advice. As a contributor to Who What Wear, Bébhinn always keeps her eyes peeled for emerging trends and looks worth writing about. She prides herself on her ability to cut through the noise and identify solid investment buys, exciting new brands and fresh takes on classic design.
- Brittany DavyEditorial Assistant
-
Low Budget, High Taste: 28 Under-$500 Items I’d Buy to Look On-Trend This Fall
Your must-have items lie ahead.
-
Elsa Hosk is My Ultimate Fall Style Muse—7 Trends I'm Stealing From Her
Plus, where I'm buying them.
-
My Mom Is in Her 50s and Asked Me for Fashion Advice—8 Chic Nordstrom Outfits I Put Together for Her Under $425
Outdated prints and "ugly" shoes included.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look Cool
See the inspiration inside.
-
Click Here for Proof That This Sophisticated Shoe Color Works With Both Jeans and Dresses
Versatile and chic.
-
This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on Repeat
Count these inspo pics as proof.
-
How I Let My Many Personalities Flourish This Fashion Month
Here's everything I wore, from New York to Paris.
-
I'm Seeing This Quietly Chic Flat-Shoe Style Paired With Outfits Everywhere This Fall
There are endless ways to wear it.