Dresses for the fall we love

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In the fall, the key to choosing the right dress is finding something that balances style with practicality, keeping you warm and comfortable as temperatures start to drop. Below, you’ll discover dresses for the fall that will have you wishing for autumnal weather.

What do you wear under a dress in the fall?

Well, that depends on the dress. To layer up, you may want tights or leggings to keep your legs warm. Depending on the dress style, you could also layer a t-shirt, shirt or polo neck underneath when the weather really starts to cool.

What kind of dress to wear in the fall?

Dresses for the fall - Karen wears a green tiered dress with boots | 40plusstyle.com

There are so many beautiful dress choices this summer. The key is to choose a dress that will work for fall, but also suits your style personality and body shape.

Karen @styledbykaren above looks fabulous in her tiered, boho style dress.

Recreate her outfit with this similar dress (another option here), boots, belt and sunglasses.

How to wear summer dresses for fall?

While the best time to choose a new dress is at the start of the season, you don’t have to rush out and buy a dress specifically for fall. You can style your summer dresses for fall by adding a jacket and boots rather than wearing them with your sandals.

Can you wear dresses in October?

Of course, you can wear a dress any month of the year. Layering is key to making your dress work for transitional weather.

What to look out for when choosing a dress for fall

When treating yourself to a new dress for the fall season, you’ll want to look out for…

Sleeves

Dresses with sleeves not only look more appropriate for fall but also keep you warmer. Another option is to choose a pinafore-style dress but wear a shirt or sweater underneath.

Fabric

Your thin, floaty summer dresses may not be suitable for fall. Instead, look for warmer, ‘tougher’ fabric choices like wool and cashmere blends, denim, leather, and corduroy.

Length

Desses for the fall that we love | 40plusstyle.com

Great lengths for fall are knee and midi styles that you can wear with your tights and boots, as shown by Dawn Lucy @fashionshouldbefun above (read her style interview here).

Check out this similar dress (another option here), jacket, tights, boots, handbag and earrings.

What kind of dress to wear in the Fall?

There are so many choices of fall dresses that you could make. Below, are some of the best…

Sweater dress

Style: A sweater dress is cozy and stylish. Choose natural materials like wool. Or, for extra luxury, opt for cashmere. That way, you’ll be both warm and comfortable.

How to wear: Pair with tights and ankle boots for a casual look, or dress up with heeled boots and a belt. When it gets even cooler, layer it with a trench coat or a long wool or cashmere coat. Don’t be afraid to choose a coat in a color choice that you wouldn’t necessarily expect for fall.

Sweater dress | 40plusstyle.com

Sam Edelman Belted Double Breasted CoatTanya Taylor Flint Rib Knit Midi DressAllSaints Tori BootsHOBO Cambel Crossbody BagMignonne Gavigan Madeline Mixed Media Mini Wing Earrings

Shirt dress

Style: A shirt dress is ideal for dressing up or down. You can wear it as it is, with a belt, or you can wear it open like a duster jacket.

How to wear: Wear loose or belt at the waist to create a different silhouette. Wear with sneakers, ankle boots of knee-high boots. You could also wear a sleeveless or chunky knit sweater on top to stay cozy. You can add a camisole underneath if you need more warmth.

Shirt dress | 40plusstyle.com

Diane von Furstenberg Tori Tie Belt Long Sleeve ShirtdressSam Edelman Sylvia Knee High BootsRebecca Minkoff Darren Leather Shoulder BagLele Sadoughi Small Dome Teardrop Earrings

Dresses for the fall - Greetje in a yellow wrap dress | 40plusstyle.com

Greetje @no_fear_of_fashion above (read her style interview here) chooses a beautiful yellow dress that would brighten up full fall days. You could easily style with sneakers or boots for a different look.

Get her look with this similar dress (another option here), pumps, handbag and necklace.

Wrap dress

Style: We love wrap dresses because they are so flattering on all body types. In fall, choose one in a heavier fabric like jersey or a wool or cashmere blend, or add layers to a lighter fabric.

How to wear: Style your wrap dress with a moto jacket and ankle or knee-high booties or wear with a blazer for a smarter look.

Wrap dress | 40plusstyle.com

Chelsea28 Long Sleeve Faux Wrap DressFranco Sarto Anna BootiesMadewell Medium Essentials Leather East/West ToteAmber Sceats Zagora Vessie Hoop Earrings

Midi dress

Style: Midi dresses are perfect for fall because they hit around mid-calf, offer more coverage than shorter dresses, and are versatile enough to be styled in lots of different ways.

How to wear: You can wear your summer midi dress by layering. When it starts to get really chilly, look for heavier fabrics like denim or jersey. Wear with sandals if it’s still warm, or pair with booties or tall boots. Add a leather moto jacket or denim jacket for layering.

Midi dress | 40plusstyle.com

ASTR The Label Emery Cropped Stretch Wool JacketAlice + Olivia Delora Cityscape Print Midi DressAllSaints Tori BootsMadewell Medium Essentials Leather East/West ToteMignonne Gavigan Madeline Mixed Media Mini Wing Earrings

Maxi dress

Style: Your maxi dress can easily be transitioned to fall. Choose darker shades, and don’t be afraid to opt for a print. Just be careful that your maxi dress doesn’t skim the floor in wet weather.

How to wear: Wear with a leather jacket and ankle boots for a boho-style look or opt for a denim jacket and sneakers for a more ‘urban’ feel.

Maxi dress | 40plusstyle.com

J.Crew Pleated Denim Lady JacketNorma Kamali Jersey Slit T-Shirt Maxi DressVionic Winny SneakersTory Burch McGraw Leather ToteChan Luu Beaded Chain Necklace

Dresses for the fall - Nicola wears a t-shirt dress and sneakers | 40plusstyle.com

Nicola @40notfrumpy above shows how you could wear your sneakers with a longer dress.

Steal her look with this similar dress (another option here), sneakers and tote.

Pinafore dress

Style: A sleeveless pinafore dress is perfect for layering over lots of tops for fall.

How to wear: Style your pinafore dress by layering over a turtleneck or shirt. Add tights, and booties or long boots.

Pinafore dress | 40plusstyle.com

Cinq à Sept Photoreal Denim Mesh Turtleneck TopNicholas the Label Shea Denim Button-Front Midi DressFranco Sarto Anna BootiesRebecca Minkoff Darren Leather Shoulder BagMignonne Gavigan Madeline Mixed Media Mini Wing Earrings

Plaid dress

Style: Plain or checks are a quintessential pattern for fall, so a plaid dress can be the perfect way to embrace fall’s aesthetic.

How to wear: A plaid dress has the same sort of look as a plaid shirt with jeans, so think about styling it the same way. Wear with sneakers or ankle boots. Add a leather jacket or a long coat to finish your look. Wear tights for extra warmth if you need to.

Plaid dress | 40plusstyle.com

Rails Everest Longline CoatNIC+ZOE Painted Plaid Bianca DressVionic Winny SneakersTory Burch McGraw Leather ToteLele Sadoughi Small Dome Teardrop Earrings

Denim dress

Style: A denim dress is very on trend right now. It’s sturdy and stylish, making it a great choice for fall.

How to wear: Depending on the style you choose, you can dress up your denim dress for an evening out. Wear it with ankle boots or sneakers for casual days or heels for dinner. You can layer a long coat, cardigan, or blazer over the top. Add a scarf that matches the formality of your outfit.

Denim dress | 40plusstyle.com

Madewell Western Long Sleeve Denim ShirtdressSam Edelman Sylvia Knee High BootsHOBO Cambel Crossbody BagAmber Sceats Zagora Vessie Hoop Earrings

Dresses for the fall - Jamie in a denim maxi dress | 40plusstyle.com

Jamie @moreturquoise above (read her style interview here) opts for boots with her denim dress. If you choose a sleeveless style, you could add a turtleneck underneath when it gets really cold.

Recreate her outfit with this similar denim dress, boots, earrings and sunglasses.

A-line dress

Style: An a-line dress is flattering, particularly for pear shapes. And, with a bit of a retro shape, it’s a fantastic style for fall.

How to wear: Think about A-line dresses from the 60s, and wear with tights and either ballet flats or boots.

A-line dress | 40plusstyle.com

Varley Maple Drawstring DressL’AGENCE Scottie High-Rise Wide Leg JeansSam Edelman Cass Ballet FlatsTory Burch McGraw Leather ToteChan Luu Beaded Chain Necklace

Your dresses for the fall outfits together in one capsule

Below, you can see all of the outfits from above together in one capsule. You could easily mix and match the outerwear, shoes, and accessories to create different looks.

Fall dresses capsule wardrobe | 40plusstyle.com

shop the items above here:



Continue reading:

  1. Fall winter 2024 fashion trends – and how to wear them
  2. Denim jacket for dresses ideas: 9 outfits featuring denim jackets with dresses
  3. The best dresses to hide your tummy

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Desses for the fall that we love | 40plusstyle.com

Feature image by Dawn Lucy @fashionshouldbefun

Sylvia

Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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