Shop September 15, 2023

Dresses, sweaters and more to transition your wardrobe from summer to fall

WATCH: How to style 1 jacket 3 ways from fall to winter

It's that time of year when we start savoring the final days of summer while simultaneously daydreaming of our new fall wardrobes.

Some of our favorite retailers have already dropped their fall collections, and naturally we're eyeing those key transitional pieces we can wear now and continue to style as temperatures drop.

For example, silk skirts are great transitional pieces, as they work with various tops and sweaters, as well as different shoes. We also love versatile cardigans, blazers (worn as a jacket or for layering!), and tailored shorts in autumnal hues.

Continue below to shop our picks!

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Summer-to-fall outerwear

Everlane The ReNew Quilted Mid-Length Liner

Price: $168 · From Everlane

This lightweight quilted liner is a perfect layering piece for the season. 

Dynamite One Button Cinched Blazer

Price: $89.95 · From Dynamite

Wear this blazer as a jacket during the summer or layer it with a turtleneck later this year. 

Quince Eco-Knit Milano Stitch Oversized Shirt Jacket

Price: $69.90 · From Quince

Shackets are another great transitional styling piece. They're lightweight enough to wear on a chilly summer evening but can also be added with warmer layers for fall.

Dynamite Cropped Zip Up Sweatshirt

Price: $54.95 · From Dynamite

If you're travelling these next couple of months, be sure to pack a sweatshirt (like this one!) for chillier nights. 

Abercrombie & Fitch Drapey Cropped Denim Jacket

Price: $90 · From Abercrombie & Fitch

This dark-wash denim jacket is currently on sale for under $80. It's also available in black. 

Summer-to-fall dresses

H&M Gathered Dress

Price: $74.99 · From H&M

Style this floral-print dress with over-the-knee black boots this fall.

Eloquii Puff Sleeve Fitted Dress

Price: $77.97 · 40% Savings
From Eloquii

Original: $129.95

This is a great summer-to-fall occasion dress because you can wear it with strappy red sandals now or with boots later.

Old Navy Fitted Long-Sleeve Rib-Knit Maxi Dress for Women

Price: $30 · 24% Savings
From Old Navy

Original: $39.99

This knit maxi dress is made from 96% cotton and is fitted throughout the body. Style it from day to night with your favorite accessories. 

By Anthropologie V-Neck Tiered Ruffle Dress

Price: $180 · From Anthropologie

This Anthropologie ruffle dress has a pretty floral print that works well in both the summer and fall. It's also a great option for an early-fall bride.

Express Ribbed High Neck Midi Sweater Dress

Price: $108 · From Express

Wear this Express high-neck sweater dress with heels and a blazer for a night out as we transition from summer to fall. 

By Anthropologie The Peregrine Midi Dress

Price: $160 · From Anthropologie

When looking for florals for fall, opt for darker color palettes, like those used for this Anthropologie Peregrine dress. 

NBD Akia Maxi Dress

Price: $188 · From Revolve

This long-sleeve maxi dress is made from a slinky jersey fabric, making it a great choice for a late summer nighttime event or another occasion this fall. 

Summer-to-fall tops

Banana Republic Bliss Silk Shirt

Price: $90 · 40% Savings
From Banana Republic

Original: $150

Style a silk shirt with a tailored Bermuda shorts when it's warm or with wool trousers when it's cold. It's also a great piece to wear day to night. 

Gap Eyelet Ruffle Perfect Shirt

Price: $41.96 · 30% Savings
From Gap

Original: $59.95

We love the ruffle detail that comes with this Gap shirt. It will look great styled beneath a jacket or worn on its own with jeans.

Gap Flannel Big Shirt

Price: $48.97 · 29% Savings
From Gap

Original: $69.95

Gap's Flannel Big Shirt comes in 7 different colors of plaid, from brown and tan to green and navy.

Mango Boat neck T-shirt

Price: $29.99 · From Mango

This boat-neck T-shirt can be worn with shorts and skirts as well as with denim, like a cool pair of wide-leg jeans.

Abercrombie & Fitch Ruched Shell Top

Price: $40 · From Abercrombie & Fitch

Style this 46% cotton and 46% modal shell top on its own when it's warm, or layer it with a light jacket in the fall.

Abercrombie & Fitch Soft Matte Seamless Tee Bodysuit

Price: $50 · From Abercrombie & Fitch

A seamless bodysuit like this one is a great layering piece for summer-to-fall dressing.

Good American Button Down 2.0 Shirt

Price: $139 · From Good American

Of course, a good white button-down is a wardrobe staple, no matter the season. 

Editor's Picks

Summer-to-fall sweaters

Banana Republic Sabel Wool-Blend Turtleneck T-Shirt

Price: $42 · 40% Savings
From Banana Republic

Original: $70

Don't be surprised when you see red trending everywhere this season. Try a red turtleneck, like this one, with black denim or trousers and a pair of slingback heels. 

Quince Mongolian Cashmere Crewneck Sweater

Price: $50 · From Quince

This 100% Grade-A mongolian cashmere sweater is just $50 from Quince. Style with jeans or a skirt throughout the autumn months. 

J.Crew Emilie patch-pocket sweater lady jacket in stripe

Price: $138 · From J.Crew

This popular J.Crew piece comes in an assortment of colors to best suit your capsule wardrobe. Wear it open over a tank or tee while it's warm or style it buttoned and with denim later in the season.

Everlane The Alpaca V-Neck Vest

Price: $98 · From Everlane

Everlane's alpaca vest is perfect for those in-between days when you don't know what to wear. Style it on its own with a pair of trousers while it's still warm or layer a turtleneck underneath come fall.

H&M Long rib-knit cardigan

Price: $49.99 · From H&M

This long, rib-knit cardigan is a great option for transitioning from summer to fall. Pair it with Bermuda shorts and a T-shirt while it's still warm and opt for the matching knit dress as temperatures cool down.

H&M Mohair-blend Top

Price: $74.99 · From H&M

Style this sweater with white shorts or light-wash denim jeans this summer, or with black pants or a leather skirt come fall. 

Summer-to-fall bottoms

Old Navy High-Waisted Mini Skirt for Women

Price: $34.99 · From Old Navy

Plaid for fall? Obviously. This cute mini-skirt would look great with black boots and a matching sweater. 

Old Navy High-Waisted Satin Cargo Jogger Pants for Women

Price: $40 · 11% Savings
From Old Navy

Original: $44.99

If you missed out on cargo pants for the summer, be sure to try them this fall. These satin pants have a partially elasticized waist and front and back pockets. Plus, you can adjust the cinched hems to wear them tight against your ankle or more loosely for a relaxed vibe. 

Everlane The TENCEL Relaxed Chino

Price: $118 · From Everlane

These Everlane chinos are super soft with a relaxed fit. Style them with a tee or a sweater depending on the weather.

Quince 100% Washable Silk Skirt

Price: $59.90 · From Quince

In our opinion, a silk skirt is a wardrobe must. Pair it with a tank in the summer or with an oversized sweater in the fall and winter. Plus, you can wear it with just about any shoe; sneakers, flats, boots and heels all work well.

Madewell Denim Mid-Rise Maxi Skirt in Pineland Wash

Price: $98 · From Madewell

This denim maxi looks great styled with a T-shirt and sandals, but we'd also love it with a slouchy sweater and boots. 

Dynamite Faux Leather Midi Skirt

Price: $59.95 · From Dynamite

This faux leather Dynamite skirt comes in both black and beige. Style with a button-down or a warmer long-sleeved knit top.

Spanx Wide Leg Jeans, Raw Indigo

Price: $168 · From Spanx

We love the way Spanx styled these indigo wide-leg jeans with a butterscotch top. The jeans could also be worn with a white or black crop top as summer comes to a close.