39 Trans-Seasonal Pieces to Wear Between Summer and Fall

It’s that time of year again when we start the slow transition into fall. While it’s too warm to pull out our heavy coats and bulky sweaters, it’ll also soon be too chilly to sport baby tees and cutoffs day after day. So rather than spending our money on summer staples at this point in the year, our best bet is to pick up pieces that will seamlessly take us into fall. Think short-sleeve turtlenecks, midi skirts and socks that can slip into sandals or booties. But getting through the in-between season takes a little bit of planning. You want to look for pieces that offer some flexibility. Items that have a touch of ventilation in the form of cut-outs or cropped hems that can be layered later on are a good jumping off point. And you need to start thinking about sweaters, sweatshirts and lightweight jackets. (Cardis and hoodies are awesome options this time of year.) You don’t need to jump from sandals to boots — look for footwear that covers your toes, but not your whole foot. Since we’re always here to help, we’ve put together a cheat sheet on the practical pieces to carry you over the hump. Here are 39 must-have picks to help you survive the (non)season.

[ Next: The 15 Items You Need to Master Trans-Seasonal Dressing ]

Summer/Fall 2018 Transition Pieces

Shirts

& Other Stories Short Sleeve Turtleneck, $29 at & Other Stories

Trade in your tank tops for more structured shirts. Look for turtlenecks with short sleeves or in sheer fabrics. Favor silky or rayon fabrics for extra breathability for those days when the temps are still high. And remember to opt for pieces that either layer under or over other pieces easily.
Shirts

Violeta by Mango Floral Flowy Shirt, $59.99 at Mango
Shirts

Calvin Klein 205W39NYC Asymmetric Check Top, $550 at Totokaelo
Shirts

The Frankie Shop Tortoise Button Ivory Belted Top, $139 at The Frankie Shop
Shirts

Zara Matching Fine Corduroy Blouse, $45.90 at Zara
Shirts

Acne Studios Floral-Print Roll-Neck Top, $180 at Matches Fashion
Shirts

J.Crew Collection Silk Twill Button-Up in Roaming Tiger Print, $120 at J.Crew
Shirts

Mango Satin Blouse, $79.99 at Mango
Shirts

Calder Pia Mock Neck Top in Lavender, $88 at Lisa Says Gah
Sweaters/Sweatshirts

Live the Process Knit Collared Cardigan, $198 at Need Supply Co.

While it's not quite sweater weather, it's always good to have one on standby. Have a cardi party or sport a sweater with a little ventilation. If going the hoodie route, set your sights on one with bold details so it feels more like a showpiece than a cover-up.
Sweaters/Sweatshirts

Eckhaus Latta Logo Hoodie, $275 at Need Supply Co.
Sweaters/Sweatshirts

See By Chloe Cut-Out Knit Sweater, $233 at Matches Fashion
Sweaters/Sweatshirts

Free People Lost In A Forest Sweater, $108 at Free People
Sweaters/Sweatshirts

H&M Tie-Detail Sweatshirt, $17.99 at H&M
Sweaters/Sweatshirts

Micha Lounge Curve Oversized Cardigan With Side Splits, $56 at ASOS
Dresses

Universal Standard for J.Crew Jersey Long-Sleeve Maxi Dress in Stripe, $130 at J.Crew

The key to wearing dresses in an in-between season is to go with ones with longer sleeves or skirts or both. Breezy fabrics and cut-outs will help you stay cool. And adding a layer will help you stay toasty when things start to cool down.
Dresses

Stelen Sienna Knotted Maxi Dress, $68 at Need Supply Co.
Dresses

Ganni Tilden Mesh Maxi Dress, $295 at Ganni
Skirts

& Other Stories Leopard Print Midi Skirt, $89 at & Other Stories

Attention: The midi is the skirt length of the season and will carry you straight through fall. For now, top with your fave tee and slip on some strappy sandals. Down the road, work in a long-sleeve shirt and mid-calf boots.
Skirts

Nanushka Gala Sarong Skirt With Cross Body Strap in Creme, $160 at Nanushka
Skirts

Maryam Nassir Zadeh Hall Skirt in Oilcloth Espresso, $315 at Lisa Says Gah
Pants

Zara Basic Culotte Pants, $29.90 at Zara

Cropped pants are your BFF this time of year. All it takes is swapping out your footwear from open to close toe to make the transition when the weather takes a turn. P.S.: Don't discount overalls because you can slip them on over everything from tees to bulky sweaters.
Pants

Stelen Maren Striped Overalls, $88 at Need Supply Co.
Pants

Eckhaus Latta Wide Leg Jean in Lagoon, $325 at Need Supply Co.
Pants

Topshop Blue Check Trousers, $80 at Topshop
Jumpsuits

Violeta by Mango Long Printed Jumpsuit, $129.99 at Mango

Jumpsuits make getting dressed easy whether it's 70 degrees or in the mid-50s. Wrap it up with a light cardigan during those colder periods.
Jackets

Ashley Rowe Cropped Denim Jacket, $225 at Need Supply Co.

Jackets (read: not coats) are a necessity. Going lightweight is the goal. Sure, your classic denim jacket will do just fine, but we like a looser approach. A linen blazer can also sub in for a jacket and can be layered over a fine-knit turtleneck come fall.
Jackets

Topshop Overhead Windbreaker Jacket, $75 at Topshop
Jackets

Urban Renewal Remade Tie-Dye Popover Jacket, $89 at Urban Outfitters
Jackets

Ganni Faulkner Jacket, $250 at Ganni
Jackets

Stüssy Clio Transparent Parka, $110 at Need Supply Co.
Jackets

Urban Outfitters Linen Blazer, $69 at Urban Outfitters
Jackets

Maeve Kirian Embroidered Crop Jacket, $128 at Anthropologie
Socks

Falke Cotton-Blend Jacquard Socks, $25 at Net-a-Porter

Keep those sandals in rotation by pairing them with some statement socks. Start by slipping on a semi-sheer pair and work your way up to thicker materials.
Socks

Free People Dippy Anklet, $12 at Free People
Shoes

Zara Leather Heeled Mules, $99.90 at Zara

You can still show a little skin, as long as your toes are covered. It's also a great time to update your sneaker wardrobe since you can run with them through fall.
Shoes

FP Collection Wanderlust Flat, $178 at Free People
Shoes

Nike Air Max 270 Sneakers, $161 at mytheresa.com
Shoes

& Other Stories Pointed Slingback Plaid Flats, $129 at & Other Stories