life·7 min read

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

summer to fall transition outfits
Design: theSkimm | Image: ASTR the Label, Reformation
Sep 8, 2022

Products you buy through our links may earn us a commission.

Summer will be wrapping up and the cooler temps will be rolling in sooner than ya know it. And depending on where you live, sometimes dressing for the weather in 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 faves for the transition between seasons. Enter: midi dresses with sleeves, easy cotton twill pants, and lightweight long-sleeve polos you can layer, mix, and match for the next couple of months. Wardrobe = hacked

A comfy midi you can dress up or down…

Choose your level of coverage thanks to its fully buttoned-up front — add a front slit by unbuttoning the bottom half, or wear it as an easy cover-up for your beach days with the top few unbuttoned. The dress is designed with short cap sleeves, made with textured cotton fabric, and available in over 10 colors. Pair it with a fan-favorite lacy bralette and some heels, or your go-to swimsuit and a beach bag. It’s easily layerable, and when the temps dip you can pair it with tights and some booties. ($98, Free People

Buy it


A classic shirtdress for an easy night-out look…

This one is made from super-smooth organically grown cotton with a sateen shine. Its chest and seam side pockets are surprisingly chic and utilitarian, and it’s available in standard, tall, and petite sizes. We rec pairing this with some wedge heels, a woven bag, and a silk headscarf. Once the temps get chilly, add some leggings and boots and you’ll be good to go. ($140, Banana Republic

Buy it


A lightweight tiered maxi perfect for running errands…

Made from 100% cotton for a lightweight feel on warmer days, it’s got layered spaghetti straps that tie in the back and a classic square neckline. We love the secret pockets and its subtle checkerboard design in three colorways. Pro tip: If you’re pulling this out on a fall day, pair it with a light to medium-weight cardigan to keep things a little toastier. ($64, Everlane)

Buy it


A long-sleeved billowing maxi for chilly nights…

This one from cult-favorite brand ASTR the Label has an off-the-shoulder design for a look that’s both classy and casual. We love its smocked high waist and tiered midi skirt that’s fully lined, so you won’t have to worry about things being see-through. It comes in two floral patterns and is the perfect option to take you from work to date night. ($158, ASTR the Label)

Buy it


A 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 pretty blue and black striped pattern and has a gold zipper accent down the back. It’s made from 100% 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)

Buy it


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

Wear this one to garden, pick up the kids, or head out to brunch with the girls — it’ll only get better with time. It’s made from soft, semi-stretch denim and has an elastic waistband. It’s super durable — meant to last you season after season — and has tons of pockets to keep any necessities handy. Keep it buttoned up all the way, or layer it with a relaxed T-shirt, dainty bralette, standout heels, or comfy sandals. ($128, Free People)

Buy it


Comfy color-blocked heels with a chunky sole…

So you can wear ’em all day without regretting it. These are great for anyone with wide feet thanks to the super flexible top band. They’re made from durable leather and come in three staple colors that’ll go with any outfit. Say hi to your new favorite accessory. ($79.90, Dolce Vita)

Buy it


A clog that’s half loafer and half slip-on…

With a synthetic leather upper, padded leather sole, and a backless design, it’s a modern take on two classics. Grab it in the chestnut or black colorway for a more academic look, or opt for the lighter cashew and maple sugar colorways perfect for pairing with your fave jeans and T-shirt or a casual midi dress. ($150, Sam Edelman)

Buy it


A sophisticated two-piece perfect for your fall weddings…

It comes in five colors — including bright pink, orange, and green — and is made from a stretch poplin fabric from organically grown and sustainably farmed cotton. The set includes a boxy, sleeveless top with side cutouts and a wraparound A-line skirt with a fitted waist. Pair it with some strappy sandals or comfy pointed flats you can dance in all night long. ($278, Reformation

Buy it


A comfy pant and versatile polo you can mix and match with tons of stuff in your closet…

The pants have a pull-on waistband (yes, please) and come in four neutral colors. They’re made from a lightweight cotton twill fabric, perfect for late summer into fall. The polo is 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 two colors, and we’re fans of its ’70s-inspired collar and silver zip-up neckline. These are two staples you’ll wanna add to cart in every color. ($65+, Everlane)

Buy it


Subscribe to Skimm Your Life

We're bringing you products, recs, and suggestions that'll make your life just a liiittle easier. It all starts with adding us to your inbox.

fbtwitteremail