We’re approaching the time of year when the temperature ranges from 60°F to 80°F within a day and choosing the right outfit for the weather feels impossible. You walk out the door in a sweater, only to experience heat exhaustion by 2 p.m. As tricky as it is, I’m using it as an excuse to test out a handful of fall trends early. Items like rugby T-shirts, miniskirts, and Mary Janes create an effortlessly cool transitional look. Or, for a more office-appropriate ensemble, opt for a sleeveless turtleneck sweater with cargo jeans and ballet flats, like the ones I’ve included below. No matter your personal style, there’s something for everyone this season. Keep scrolling to shop the 25 trending items I’d buy to achieve the perfect summer-to-fall transition wardrobe.
Prepare to see rugby shirts everywhere this season.
Lioness
Slouched Tie Up Jeans
I’ve seen versions of these jeans for triple the price.
Marc Joseph New York
East Village Penny Loafer
A preppy penny loafer is at the top of my fall shopping list.
Abercrombie & Fitch
Cropped Twill Workwear Jacket
We saw workwear jackets emerge in the spring, and I expect them to pick up even more momentum this fall.
Scoop
Scoop Ultimate Turtleneck Sweater Shell
If you look up transition wardrobe in the dictionary, a picture of this sleeveless tank pops up.
Wilfred
Strut Wide Cargo Jean
I love that these cargo jeans have a relaxed look to them without looking like parachute pants.
Franco Sarto
Mary Jane Flat
A trending shoe in a trending color coming right up.
I own this exact bag in brown, and it has quickly become the one I use most. I think the black colorway transitions nicely into the new season.
Banana Republic
Twisted Halter Top
I’d copy and paste this entire look and wear it to the office.
Almina Concept
Linen Bermuda Shorts
You won’t regret purchasing these shorts for those 70-degree fall days.
Re/Done
Off-White ‘Back to Reality’ T-Shirt
Nothing screams “summer’s over” like this cute tee.
My entire Instagram feed is inundated with cute miniskirts like this one.
Adidas
Gazelle Indoor Shoes
A pop of yellow does an outfit good.
GANNI
Beige Leopard Oversized Canvas Tote
Leopard print is making a comeback this season.
Jenni Kayne
Ribbed Finley Cardigan
The ’90s vibe of this cardigan feels Rachel Green–approved.
Everyone has black-and-white Sambas, but not everyone has white-and-green Sambaes.
Banana Republic
Oversized Denim Trench Coat
Another fabulous light-layer option.
A fall wedding guest dress for under $100? Incredible.
Schutz
Dethalia Dress Sandal
Here’s the kitten heel I’d style with that Nia dress.
Staud
Brown Vivi Shoulder Bag
It’s not fall without a brown suede shoulder bag.
ALIGNE
Mitch Cord Waistcoat
…or this corduroy waistcoat.
Anne Klein
Goldtone Gray Dial Watch
Watches have been a key accessory for a few seasons now. If you’re not ready to make a big investment, I recommend this Anne Klein style for under $100.
J. Crew
Pleated Denim Mini Skort
What did I tell you about the super cute miniskirts? They’re everywhere!
Franco Sarto
Kitten Heel Mary Janes
To round out the preppy look, wear these sweet Mary Janes.
