Every Fall Outfit I Want to Wear This Year (So Far)
If you’re looking for the kind of outfits that are effortless and the definition of cool.


There’s nothing a fashion person looks forward to more than fall. The crisp crunch of the leaves, the layers of decadent fabrics, the feeling of a new beginning—it’s the season that makes me want to romanticize getting dressed again. By August, I usually hit a wall with summer fashion and find myself craving the moodier palette, heavier textures, and all the layering possibilities that autumn has to offer. We've officially reached that time of year and it has me getting excited for what fall has to offer.
So far this year, my saved folder has been filling up with outfits that feel effortless but still pack a serious cool factor. These are the kinds of looks you can throw on without overthinking and somehow still look like you’ve got it all figured out. My goal with curating this list was to make sure to choose several looks that you can easily recreate with what's already in your closet—you're welcome. From low-key denim pairings to elevated outerwear moments, here’s everything I’m planning to wear the second the temperature drops.
Funnel Neck Jacket + Flannel
Funnel neck jackets really did their big one last year and they don't seem to be going away anytime soon. Style them with a flannel wrapped around the waist to add a 2025 touch to your look.
Leopard Pants + Trench Coat
Another item that I was loving last fall was a good pair of leopard pants. I can't wait to wear them again this season with a good pair of pumps and a trench coat.
Denim Jacket + Sweater Over Shoulders
Here's an outfit you can easily recreate with what's in your closet. Give your old denim jacket and upgrade by styling it by draping a sweater over your shoulders, you'll naturally be obsessed.
Maxi Dress + Statement Trench Coat
You simply can’t go wrong with this combination, it always feels like a major moment. I love the choice of a suede trench coat because let’s be real, it’s simply a trend that’s not going anywhere.
Slim-Fit Jeans + Pop of Color Heels
Here’s for an outfit that Carrie Bradshaw would approve of. Any pair of jeans looks even cooler when you add a really great pair of shoes.
Layered Sweater + Flare Jeans
This is the kind of outfit that I would imagine on a modern day Princess Diana. A preppy baseball hat with a button-down shirt layered under a sweater and flared denim. Incredibly stylish without doing too much.
Belted Mini Skirt + Clutch
Even though longer iterations of your favorite skirt are more popular right now than ever, when styled right a mini can make a major impact. A ‘90s-esque clutch will do the trick.
Trench Bomber + Button-Down Shirt + Flared Pants
I’ve never seen an outfit that better combined the Saint Laurent and Toteme aesthetic into just one look. I didn’t think my first purchase of the season would be flared pants but I’ve officially been convinced.
Glasses + Plaid Skirt + Turtleneck
Clearly whenever fall comes around, I have preppy on the mind. This makes me pull out a plaid skirt and optical lenses bringing me right back to my school uniform days. Obsessed.
Military Jacket + Jeans + Pumps
A good jacket with plenty of buttons has a way of winning me over every time. When you have a couple of jackets like this, you're always going to have outfit ideas galore. Just add your favorite pair of jeans.
Leather Jacket + Sheer Skirt
A night out in the fall is always made better when you add a sheer coat and a really great leather piece to go right with it. The contrast between a heavy and a light fabric always wins me over.
Wool Coat + Printed Jeans
The colder days of fall are always made better when you have a wool coat like this. A statement pair of jeans is the perfect thing to style it with.
Flannel + Leather Midi Skirt
Keep them on their toes. This fall will be styling unexpected wardrobe staples together. Who would’ve though a plaid flannel would look so good with a leather pencil skirt.
Denim on Denim
Because it simply never fails me. Whenever I don’t have much time to think about my outfit, I know I’ll look elevated in denim on denim. In the early fall days, I’d style it with a kitten heel and as things cool down boots can bring a whole new vibe to the final look.
Polo Shirt + Socks + Pumps
Polo shirts have been giving me so much nostalgia lately. If you want to look librarian chic style the look with sheer socks and cool pumps.

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
-
Hailey Bieber Wore Vintage Tom Ford Gucci Sandals With the Summer Pant Trend I See Sticking Around Through Fall
Any pants that look this good shouldn't be packed up just because the season changes.
-
Your Fall Capsule Wardrobe Has Arrived—28 Pieces From NET-A-PORTER That Scream "Elegant and Classic"
Closet refresh time!
-
Everyone Is Suddenly Wearing This Expensive-Looking Item With White Pants
So chic.
-
All of My Most Stylish Friends Are Already Carrying This Fall Bag Trend
And it's luxe.
-
Forget Lace-Up Boots: This Casual and Easy Boot Trend Is About to Be Everywhere
Make this your first boot purchase for the season.
-
No One Wears a White T-Shirt Quite Like a Fashion Person—6 Incredibly Cool Looks to Re-Create Now
Nothing but chic, effortless vibes.
-
FYI: Every Fashion Person Is Buying This Pretty Shoe Color Instead of Black Right Now
Count us in.
-
The 8 Trendy Basics That Will Define Fall 2025
From denim to flats.
-
Goodbye, Linen Trousers—Starting Now, This Pretty Pant Trend Will Be on Fashion People Everywhere
I guarantee it.
-
Basic Jeans Aren't Out, But This Denim Trend Feels Way More 2025
It's not white, dark wash, or chocolate brown.