• Video
  • Shop
  • Culture
  • Family
  • Wellness
  • Food
  • Living
  • Style
  • Travel
  • News
  • Book Club
  • GMA3: WYNTK
  • Newsletter
  • Privacy Policy
  • Your US State Privacy Rights
  • Children's Online Privacy Policy
  • Interest-Based Ads
  • Terms of Use
  • Do Not Sell My Info
  • Contact Us
  • © 2025 ABC News
  • Shop

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

1:31
How to style 1 jacket 3 ways from fall to winter
ABC News Photo, Abercrombie & Fitch, Dynamite Clothing, Spanx, Mango, J.Crew
ByClaire Peltier
September 15, 2023, 3:42 PM

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!

Get more shopGMA! Sign up for our newsletter, and follow on Instagram and TikTok.

By clicking on these shopping links, visitors will leave Goodmorningamerica.com. These e-commerce sites are operated under different terms and privacy policies than Goodmorningamerica.com. ABC will receive a commission for purchases made through these links. Prices may change from the date of publication.

Summer-to-fall outerwear

Everlane

Everlane The ReNew Quilted Mid-Length Liner

This lightweight quilted liner is a perfect layering piece for the season. 
  • $168
  • Everlane
Shop Now
Dynamite

Dynamite One Button Cinched Blazer

Wear this blazer as a jacket during the summer or layer it with a turtleneck later this year. 
  • $89.95
  • Dynamite
Shop Now
Quince

Quince Eco-Knit Milano Stitch Oversized Shirt Jacket

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.
  • $69.90
  • Quince
Shop Now
Dynamite

Dynamite Cropped Zip Up Sweatshirt

If you're travelling these next couple of months, be sure to pack a sweatshirt (like this one!) for chillier nights. 
  • $54.95
  • Dynamite
Shop Now
Abercrombie & Fitch

Abercrombie & Fitch Drapey Cropped Denim Jacket

This dark-wash denim jacket is currently on sale for under $80. It's also available in black. 
  • $90
  • Abercrombie & Fitch
Shop Now

Summer-to-fall dresses

H&M

H&M Gathered Dress

Style this floral-print dress with over-the-knee black boots this fall.
  • $74.99
  • H&M
Shop Now
39% off
Eloquii

Eloquii Puff Sleeve Fitted Dress

This is a great summer-to-fall occasion dress because you can wear it with strappy red sandals now or with boots later.
  • $77.97
  • $129.95
  • Eloquii
Shop Now
24% off
Old Navy

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

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. 
  • $30
  • $39.99
  • Old Navy
Shop Now
Anthropologie

By Anthropologie V-Neck Tiered Ruffle Dress

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.
  • $180
  • Anthropologie
Shop Now
Express

Express Ribbed High Neck Midi Sweater Dress

Wear this Express high-neck sweater dress with heels and a blazer for a night out as we transition from summer to fall. 
  • $108
  • Express
Shop Now
Anthropologie

By Anthropologie The Peregrine Midi Dress

When looking for florals for fall, opt for darker color palettes, like those used for this Anthropologie Peregrine dress. 
  • $160
  • Anthropologie
Shop Now
Revolve

NBD Akia Maxi Dress

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. 
  • $188
  • Revolve
Shop Now

Summer-to-fall tops

40% off
Banana Republic

Banana Republic Bliss Silk Shirt

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. 
  • $90
  • $150
  • Banana Republic
Shop Now
30% off
Gap

Gap Eyelet Ruffle Perfect Shirt

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.
  • $41.96
  • $59.95
  • Gap
Shop Now
29% off
Gap

Gap Flannel Big Shirt

Gap's Flannel Big Shirt comes in 7 different colors of plaid, from brown and tan to green and navy.
  • $48.97
  • $69.95
  • Gap
Shop Now
Mango

Mango Boat neck T-shirt

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.
  • $29.99
  • Mango
Shop Now
Abercrombie & Fitch

Abercrombie & Fitch Ruched Shell Top

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.
  • $40
  • Abercrombie & Fitch
Shop Now
Abercrombie & Fitch

Abercrombie & Fitch Soft Matte Seamless Tee Bodysuit

A seamless bodysuit like this one is a great layering piece for summer-to-fall dressing.
  • $50
  • Abercrombie & Fitch
Shop Now
Good American

Good American Button Down 2.0 Shirt

Of course, a good white button-down is a wardrobe staple, no matter the season. 
  • $139
  • Good American
Shop Now

Editor’s Picks

Shop all the jeans you need for spring: Wide-leg, straight, flared and more

  • Apr 10, 2025

Women's flats for spring: Mary Janes, loafers and more shoes you'll love

  • May 02, 2025

I tried 29 red lipsticks: Shop my picks for lasting color, matte finishes and more

  • Jul 29, 2024

Summer-to-fall sweaters

40% off
Banana Republic

Banana Republic Sabel Wool-Blend Turtleneck T-Shirt

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. 
  • $42
  • $70
  • Banana Republic
Shop Now
Quince

Quince Mongolian Cashmere Crewneck Sweater

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

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

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.
  • $138
  • J.Crew
Shop Now
Everlane

Everlane The Alpaca V-Neck Vest

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.
  • $98
  • Everlane
Shop Now
H&M

H&M Long rib-knit cardigan

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.
  • $49.99
  • H&M
Shop Now
H&M

H&M Mohair-blend Top

Style this sweater with white shorts or light-wash denim jeans this summer, or with black pants or a leather skirt come fall. 
  • $74.99
  • H&M
Shop Now

Summer-to-fall bottoms

Old Navy

Old Navy High-Waisted Mini Skirt for Women

Plaid for fall? Obviously. This cute mini-skirt would look great with black boots and a matching sweater. 
  • $34.99
  • Old Navy
Shop Now
11% off
Old Navy

Old Navy High-Waisted Satin Cargo Jogger Pants for Women

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. 
  • $40
  • $44.99
  • Old Navy
Shop Now
Everlane

Everlane The TENCEL Relaxed Chino

These Everlane chinos are super soft with a relaxed fit. Style them with a tee or a sweater depending on the weather.
  • $118
  • Everlane
Shop Now
Quince

Quince 100% Washable Silk Skirt

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.
  • $59.90
  • Quince
Shop Now
Madewell

Madewell Denim Mid-Rise Maxi Skirt in Pineland Wash

This denim maxi looks great styled with a T-shirt and sandals, but we'd also love it with a slouchy sweater and boots. 
  • $98
  • Madewell
Shop Now
Dynamite

Dynamite Faux Leather Midi Skirt

This faux leather Dynamite skirt comes in both black and beige. Style with a button-down or a warmer long-sleeved knit top.
  • $59.95
  • Dynamite
Shop Now
Spanx

Spanx Wide Leg Jeans, Raw Indigo

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. 
  • $168
  • Spanx
Shop Now

Editor’s Picks

Shop all the jeans you need for spring: Wide-leg, straight, flared and more

  • Apr 10, 2025

Women's flats for spring: Mary Janes, loafers and more shoes you'll love

  • May 02, 2025

I tried 29 red lipsticks: Shop my picks for lasting color, matte finishes and more

  • Jul 29, 2024

Up Next in Shop—

'GMA' Deals & Steals on summer accessories

June 21, 2025

ABC Secret Sales on clever solutions

June 21, 2025

Early Fourth of July deals to shop now: Clothing, mattresses and more

June 20, 2025

Essential white T-shirts for summer, starting at under $10

June 20, 2025

Shop GMA Favorites

ABC will receive a commission for purchases made through these links.

Sponsored Content by Taboola

The latest lifestyle and entertainment news and inspiration for how to live your best life - all from Good Morning America.
  • Contests
  • Terms of Use
  • Privacy Policy
  • Do Not Sell My Info
  • Children’s Online Privacy Policy
  • Advertise with us
  • Your US State Privacy Rights
  • Interest-Based Ads
  • About Nielsen Measurement
  • Press
  • Feedback
  • Shop FAQs
  • ABC News
  • ABC
  • All Videos
  • All Topics
  • Sitemap

© 2025 ABC News
  • Privacy Policy— 
  • Your US State Privacy Rights— 
  • Children's Online Privacy Policy— 
  • Interest-Based Ads— 
  • Terms of Use— 
  • Do Not Sell My Info— 
  • Contact Us— 

© 2025 ABC News