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

VIDEO: How to style 1 jacket 3 ways from fall to winter
1:31
How to style 1 jacket 3 ways from fall to winter
ABCNews.com
ByClaire Peltier
August 14, 2023, 6:01 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!

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Summer-to-fall outerwear

Everlane

Everlane The ReNew Quilted Mid-Length Liner

  • $168
  • Everlane

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

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Dynamite

Dynamite One Button Cinched Blazer

  • $89.95
  • Dynamite

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

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Quince

Quince Eco-Knit Milano Stitch Oversized Shirt Jacket

  • $69.90
  • 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.

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Dynamite

Dynamite Cropped Zip Up Sweatshirt

  • $54.95
  • Dynamite

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

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Abercrombie & Fitch

Abercrombie & Fitch Drapey Cropped Denim Jacket

  • $90
  • Abercrombie & Fitch

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

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Summer-to-fall dresses

H&M

H&M Gathered Dress

  • $74.99
  • H&M

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

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39% off
Eloquii

Eloquii Puff Sleeve Fitted Dress

  • $77.97
  • $129.95
  • Eloquii

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

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24% off
Old Navy

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

  • $30
  • $39.99
  • Old Navy

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. 

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Anthropologie

By Anthropologie V-Neck Tiered Ruffle Dress

  • $180
  • 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.

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Express

Express Ribbed High Neck Midi Sweater Dress

  • $108
  • Express

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

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Anthropologie

By Anthropologie The Peregrine Midi Dress

  • $160
  • Anthropologie

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

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Revolve

NBD Akia Maxi Dress

  • $188
  • 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. 

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Summer-to-fall tops

40% off
Banana Republic

Banana Republic Bliss Silk Shirt

  • $90
  • $150
  • Banana Republic

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. 

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30% off
Gap

Gap Eyelet Ruffle Perfect Shirt

  • $41.96
  • $59.95
  • Gap

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.

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29% off
Gap

Gap Flannel Big Shirt

  • $48.97
  • $69.95
  • Gap

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

Shop Now
Mango

Mango Boat neck T-shirt

  • $29.99
  • 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.

Shop Now
Abercrombie & Fitch

Abercrombie & Fitch Ruched Shell Top

  • $40
  • 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.

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Abercrombie & Fitch

Abercrombie & Fitch Soft Matte Seamless Tee Bodysuit

  • $50
  • Abercrombie & Fitch

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

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Good American

Good American Button Down 2.0 Shirt

  • $139
  • Good American

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

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Editor’s Picks

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Summer-to-fall sweaters

40% off
Banana Republic

Banana Republic Sabel Wool-Blend Turtleneck T-Shirt

  • $42
  • $70
  • Banana Republic

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. 

Shop Now
Quince

Quince Mongolian Cashmere Crewneck Sweater

  • $50
  • Quince

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

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J.Crew

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

  • $138
  • 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.

Shop Now
Everlane

Everlane The Alpaca V-Neck Vest

  • $98
  • 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.

Shop Now
H&M

H&M Long rib-knit cardigan

  • $49.99
  • 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.

Shop Now
H&M

H&M Mohair-blend Top

  • $74.99
  • 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. 

Shop Now

Summer-to-fall bottoms

Old Navy

Old Navy High-Waisted Mini Skirt for Women

  • $34.99
  • Old Navy

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

Shop Now
11% off
Old Navy

Old Navy High-Waisted Satin Cargo Jogger Pants for Women

  • $40
  • $44.99
  • Old Navy

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. 

Shop Now
Everlane

Everlane The TENCEL Relaxed Chino

  • $118
  • Everlane

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

Shop Now
Quince

Quince 100% Washable Silk Skirt

  • $59.90
  • 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.

Shop Now
Madewell

Madewell Denim Mid-Rise Maxi Skirt in Pineland Wash

  • $98
  • 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. 

Shop Now
Dynamite

Dynamite Faux Leather Midi Skirt

  • $59.95
  • Dynamite

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

Shop Now
Spanx

Spanx Wide Leg Jeans, Raw Indigo

  • $168
  • 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. 

Shop Now

Editor’s Picks

Shop all the jeans you need in your wardrobe: Wide-leg, straight, flared and more

  • Aug 11, 2023

Comfortable women's flats for fall: Shop ballet flats, loafers and more

  • Sep 13, 2023

I tried 27 red lipsticks: Shop my picks for long-lasting color, matte finishes and more

  • Aug 08, 2023
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