Shopping·9 min read

14 Transitional Clothing Pieces That’ll Get You Excited for Fall

summer to fall transition outfits
Design: theSkimm | Image: Everlane, Reformation
September 22, 2023

This post was originally published in April 2022 and has been updated.

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Depending on where you live, dressing for the weather between seasons and into the fall can be tricky: You don't want to sweat during those warmer days, but chillier nights mean being prepared to cover up a bit. Which is why we pulled together some of our favorite clothes, shoes, and accessories for the transition between seasons. Think midi dresses with sleeves, easy trousers, and lightweight sweaters you can layer, mix, and match for the next couple of months. Wardrobe = hacked

summer to fall transitional outfits
Free People

A lightweight jacket you can pack up in your bag…

The only thing worse than being cold is having to carry a bulky jacket around all day. For those early fall days that seem to jump from hot to cold in a matter of hours, this packable jacket will be your BFF. It comes in seven colors and has ruched sleeves and a cropped, drawstring hem. The real draw is that it folds up into a tiny little package that you can stuff in your tote. Genius. ($90, Free People

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Shirt dress summer to fall transitional outfits
Banana Republic

A classic shirtdress for an easy night-out look…

This one is made from crisp cotton poplin. We can’t get over the puffed sleeves, and the A-line fit offers more structure than your typical loose shirtdress. We love that it’s available in standard, tall, and petite sizes, too. We rec pairing this with some wedge heels and a printed headscarf. Once the temps get chilly, add some leggings and boots, and you’ll be good to go. ($160, Banana Republic

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Nursing jumpsuit summer to fall transitional outfits
Madewell

A maternity jumpsuit with a crossover front for easy breastfeeding…

No matter where you are. Simply lift either side of the front of the jumpsuit to tend to your baby. This one comes in a blue pinstripe and a black and has a gold zipper accent down the back. It’s made from cotton, and it’s machine-washable so you can get those pesky milk stains out in a cinch. Customers say it’s a seamless, chic addition to their postpartum wardrobe. ($298, Madewell)

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summer to fall transitional outfits
Free People

Utility-inspired coveralls that are equal parts comfy and chic…

Wear these short-sleeve coveralls to garden, pick up the kids, or head out to brunch — the more worn-in, the better. They’re made from soft, semi-stretch denim and have an elastic waistband. They’re super durable — meant to last you season after season — and have tons of pockets to keep any necessities handy. Keep this piece buttoned up all the way up, or layer it with a turtleneck and boots when the weather gets colder. ($128, Free People)

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summer to fall transitional outfits
Reformation

A sophisticated two-piece perfect for your fall weddings…

It’s available in two colors — cherry red and mint green (and navy, coming soon) — and is made from a soft, stretchy jersey fabric. The set includes a figure-hugging tube dress with a matching cardigan perfect for transitioning from day to night. Pair it with some strappy sandals or comfy pointed flats you can dance in all night long. Style the cropped cardigan with high-waisted jeans or trousers when the party’s over. ($168, Reformation

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High top sneakers
Farfetch

Cool high-tops for everyday wear…

Whether sneakers are already a part of your rotation or you’re thinking of branching out, these high-tops from cult brand Autry should be first on your add-to-cart list. The lining and outer are made from 100% leather, and the insole will conform to your foot with wear. Pair them with your favorite jeans and white tee over the weekend, or style them up with trousers and a button-down for your next casual in-office day. ($170, Farfetch)

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Comfy Pants
Everlane

Comfy pants you can mix and match…

These come in three neutral colors and are made from super comfy knit (yes, please), perfect for late summer into fall. They’ve got a hidden side zipper, a slight flare at the hem, and the fabric feels like your favorite pair of leggings. Customers say they fit true to size and love the minimalist detailing. ($98, Everlane)

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Lightweight polo
Everlane

A lightweight polo made from ultra-soft wool…

It’s super soft and semi-lightweight, with long sleeves to keep you warm during chillier nights and a tight fit that’s ideal for layering. It comes in three colors, and we’re fans of its ’70s-inspired collar and button-up neckline. Go ahead. Add every color to cart. ($118, Everlane)

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Loafers
Camper

Chunky loafers that make a statement…

This staple shoe has a chunky sole that’ll add some height, a calfskin upper, and a super-cushioned sole that’ll provide support and comfort. We’re a fan of the Barbiecore pink colorway, but if that’s not your vibe, pick one of the nine other neutral colors on offer — they’ll still make a sartorial statement. We highly recommend snagging some leather cleaner to protect and buff your kicks whenever they need a little TLC. ($190, Camper)

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Boots
Banana Republic

Knee-high boots you’ll wear season after season…

We’re horse girls at heart, so we can’t help but love these equestrian-inspired leather boots. They sit right below the knee and have a crossover belt accent at the top. The sleek silhouette is complete with a flattering round toe and a wearable, ultra-low heel. Get them in either deep brown or black, and pair them with your favorite long-sleeve dress while you still can. ($450, Banana Republic

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Cardigan
Reformation

A light cardigan perfect for the end of summer…

Who doesn’t love a staple cardigan? You’ll be reaching for this one every chance you get. It comes in three colors and has a simple silhouette that’ll pair with almost anything in your wardrobe. Hand wash it and lay to dry to keep it from pilling. ($198, Reformation)

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Polo pullover
Quince

A polo pullover sweater for when it gets chilly…

Effortless looks for the win. This collared cotton sweater looks smart and sophisticated. Add your favorite necklaces and you’ll have a chic top layer in seconds. Brownie points for the fact that this isn’t a splurge. ($49.90, Quince)

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Fleece socks
Alo Yoga

Super soft fleece socks that feel like a hug for your feet…

We’ve got these in both colors, and we’re begging for more. They’re soft, fluffy, and don’t fall down thanks to the elastic stretch. They’re durable and easy to clean, too, so you can wear them every day (we know you’ll want to). ($20, Alo Yoga

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Sweats
Buck Mason

A hoodie and sweats set you’ll want in every color…

We haven’t been able to take this hoodie and sweats set off since we brought it home. Both pieces are made from a French terry that’s lightweight and breathable and has a slim-cut silhouette that elevates it a couple notches. Wear it around the house, on your next coffee run, or for casual lunches. Hello, versatility. ($98, Buck Mason)

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