25 Smart Pieces I'd Add to My Wardrobe as We Transition from Summer to Fall

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.

Madewell Rugby Polo Tee

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.

St Agni Petit Bagu

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.

Reformation Viv Skirt

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.

AG Thalia Shorts

The jort trend lives on.

Adidas Sambae Shoes

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.

Nia Santal Dress

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.