How to Wear Dresses in the Fall

Got a closet full of cute dresses but you aren't sure how to wear them when the weather turns cool? You're in luck! Dresses are easy to layer and dress up or down, making them the perfect fall wardrobe staple. Transition your dresses into the fall season by layering them with tops and outerwear such as sweaters, jackets, and coats. Add some cute cold-weather accessories, such as a scarf and a hat, and complete the look with a stylish pair of footwear. Rock your finished fall-weather look with confidence!

1

Wear a simple white T-shirt under a slip dress.

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    You'll instantly look casual and stylish. The T-shirt will keep your neck and shoulders warm, and it will balance out the chic slip dress with a casual element. Make sure to pair this outfit with a long, warm overcoat, since slip dresses are made of a thin material.[1]
    • For example, you could pair a long, olive-colored slip dress with a white T-shirt and a blazer-style overcoat.
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2

Get cozy with a chunky sweater over a dress.

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    Try on various lengths of sweaters and dresses to create different looks. For example, you could wear a longer sweater that lets a bit of dress peek out at the bottom, or you could pair a cropped sweater and a dress with a fuller skirt. You could also go for the classic dress and cardigan pairing.[2]
    • For a playful, cute look, put a long red sweater over a shorter cream-colored dress and a pair of ankle boots. If it’s cold out, add some tights or tall socks.
3

Layer a fitted turtleneck under a sleeveless dress.

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    This clean silhouette is simple and chic. A long-sleeved top will keep you warm and streamline your outfit. Choose a close-fitting turtleneck made of thinner material to pair underneath your dress, such as a thin cotton or rayon material. Avoid bulkier turtlenecks made from wool or with a chunky knit pattern, which will make the dress look lumpy and wrinkly.[3]
    • For example, you could wear a simple cream turtleneck underneath a sleeveless mustard-colored dress.
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4

Go modern minimalist with a shift dress over trousers.

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    Add a crisp button-down oxford and heels to complete the look. This style combines 60s-style tailoring, office-wear chic, and clean lines.[4]
    • To try this style, wear a white button-down shirt, a pair of cream dress pants, and a structured, rust-colored shift dress. For footwear, opt for a pair of black heels.
5

Wear a leather jacket over a floral dress for an edgy touch.

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    A tough-looking jacket will warm up any summer dress. The combination of a feminine floral pattern and a structured leather jacket can balance out a cute outfit with a tough, cool piece. [5] This look also works well for both daytime and nighttime.[6]
    • For example, you could wear a black dress with a pink and white floral pattern beneath a simple black moto-style leather jacket.
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6

Wear a fancier coat to elevate your look.

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    Stylish outerwear can make the outfit stylish and work-appropriate. Options such as a camel coat, a lightweight trench coat, and a thick blazer look especially good with a midi-length dress, which ends mid-calf, or a shift dress.[7]
    • A camel coat combines the perfect color and thick, warm fabric for a fall outfit. Pair it with a fitted black midi-length dress for a simple, sophisticated outfit.
    • The combination of a boxy, masculine blazer and a flowy, feminine dress is a popular style, perfect for wearing around town or to the office.[8]
    • Try wearing a blush trench coat over a navy shirtdress for a Parisian-inspired outfit.
7

Opt for a casual jacket to dress down the look.

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    Pick a bomber jacket or denim jacket to keep things casual. This is a popular street style look, perfect for attending casual events, running errands, or going out for the night.
    • Try wearing a taupe slip dress with a simple white T-shirt under an olive green bomber jacket for an effortlessly cool look.
    • You could also pair a summer dress with a dark-wash denim jacket and a pair of tights for a casual but put-together outfit.
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8

Wear a pair of opaque tights for warmth and coverage.

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    Tights are a perfect addition to make your outfit cold weather-ready. You could go for a pair of classic black tights, or try a more daring color like navy or burgundy. When the fall weather starts to turn even colder, switch your normal tights to a pair that’s fleece-lined.
    • For example, you could wear a pair of fleece-lined black tights underneath a burgundy sweater dress and a light grey coat for maximum warmth. Finish the look with some black leather riding boots.
9

Cinch the waist in with a belt to make a silhouette more flattering.

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    This is great if you're layering with a flowy dress. Add a belt to a loose, baggy dress to emphasize your waist and add a point of interest to the outfit.[9] You could choose a simple black belt with a metal buckle, or you could go for something with more detail, such as an embroidered, chain, or suede belt.
    • For example, you could cinch in a denim shirt dress with a black leather belt that features a vintage silver buckle. Add a pair of suede ankle boots and a patterned scarf to complete the look.
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10

Add a long, soft blanket scarf for warmth and versatility.

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    A blanket scarf is a cozy touch in cold weather. Wear your blanket scarf wrapped around the neck or as a wrap, depending on how cold it is outside. Choose a soft, lightweight fabric and a neutral color, such as black, gray, navy, taupe, or cream.[10]
    • Pair an olive-colored shift dress with a cream-colored coat and arrange a taupe blanket scarf around your shoulders. Add a pair of tall brown suede boots.
11

Add a knit or felt hat to complete the outfit.

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    Pretty knit hats are both cute and functional. Pair these with more casual outfits.[11] Brimmed felt hats also add some stylishness to the outfit, particularly when paired with dressier outfits.
    • Pair a black-and-white striped T-shirt dress with a pink bomber jacket, then add a white beanie and white sneakers to create a casual cool-weather look.
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12

Go with a pair of tall boots to stay warm and chic.

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    Taller boots will help keep your legs warm. Choose between a classic pair of knee-high riding boots or a daring pair of fitted over-the-knee suede boots.[12] Wear some tights or add a pair of cozy knit socks to your riding boots for extra warmth.
    • Let the tops of the socks peek out above the boots for a cozy, layered look.
    • For example, you could pair some charcoal suede over-the-knee boots with a black fitted turtleneck and a burgundy sleeveless dress.
13

Opt for a classic pair of ankle boots for style and versatility.

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    Ankle boots are a popular fall staple. They're perfect for pairing with any length of dress, from summer dresses to maxi dresses.[13] Choose a sleek leather pair for instant class or a pair in suede for a soft, autumnal texture.[14]
    • For example, you could wear a rust-colored T-shirt dress with a chunky cream-colored cardigan and some tan leather ankle boots.
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14

Trade in your summer sandals for heels.

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    Go classic with a pair of pumps. Pairing your summer dresses with heels instead of sandals will help you stay warm, chic, and fall-appropriate. Go for a pair in a neutral shade, such as black, navy, or taupe, and choose a pair of opaque tights that matches.
    • For example, you could wear a patterned, burgundy summer dress with some black tights and a pair of black pumps. Add a warm gray blazer to finish off the look.

Community Q&A

  • Question
    How do I wear summer dresses in fall?
    Stephanie Fajardo
    Stephanie Fajardo
    Professional Stylist
    Stephanie Fajardo is a Personal Stylist based in Portland, Oregon. Stephanie has over 17 years of styling experience in personal consulting, television, photography, and film shoots. Her work has been featured in Esquire Magazine and Portland Fashion Week.
    Stephanie Fajardo
    Stephanie Fajardo
    Professional Stylist
    Expert Answer
    Denim jackets and ponchos are great ways to style a dress in the fall, especially with a pair of boots or chunky sneakers.
  • Question
    Should I worry about how I look? People say I look hideous and they laugh at me.
    Community Answer
    Community Answer
    No, you shouldn't let them talk to you like that. Dress how you want to and be yourself.
  • Question
    Can this apply for boys too?
    Aditi
    Aditi
    Community Answer
    These steps can apply for any gender identity. If you like wearing dresses, these steps apply, regardless of whether you’re a boy or a girl.
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References

  1. ↑ https://verilymag.com/2017/10/transitional-wardrobe-maxi-dresses-midi-skirts-fall-wardrobe-fall-trends-how-to-wear-dresses-in-fall
  2. ↑ http://stylecaster.com/how-to-wear-summer-dresses-in-fall/
  3. ↑ http://stylecaster.com/how-to-wear-summer-dresses-in-fall/
  4. ↑ http://www.thefashionspot.com/style-trends/654309-how-to-wear-summer-dresses-in-fall/#/slide/10
  5. ↑ http://www.thefashionspot.com/style-trends/654309-how-to-wear-summer-dresses-in-fall/#/slide/2
  6. ↑ https://www.justthedesign.com/rev-up-your-wardrobe-with-these-leather-jacket-outfits/
  7. ↑ https://www.liveabout.com/how-to-pair-jackets-with-dresses-2780958
  8. ↑ https://www.glamour.com/gallery/fall-fashion-the-dos-and-donts-of-transitioning-your-wardrobe-from-summer-to-fall#17
  9. ↑ http://www.cosmopolitan.com/entertainment/celebs/news/a17589/belting-tips/
  1. ↑ http://www.cosmopolitan.com/style-beauty/fashion/how-to/a47395/12-ways-to-wear-a-blanket-scarf/
  2. ↑ https://www.glamour.com/gallery/fall-fashion-the-dos-and-donts-of-transitioning-your-wardrobe-from-summer-to-fall#4
  3. ↑ http://stylecaster.com/how-to-wear-summer-dresses-in-fall/
  4. ↑ http://www.thefashionspot.com/style-trends/654309-how-to-wear-summer-dresses-in-fall/#/slide/2
  5. ↑ https://www.realsimple.com/beauty-fashion/shoes-accessories/shoes/how-to-wear-ankle-boots
  6. ↑ https://www.glamour.com/gallery/fall-fashion-the-dos-and-donts-of-transitioning-your-wardrobe-from-summer-to-fall#4
  7. ↑ https://www.glamour.com/gallery/fall-fashion-the-dos-and-donts-of-transitioning-your-wardrobe-from-summer-to-fall#11

About This Article

Stephanie Fajardo
Co-authored by:
Stephanie Fajardo
Professional Stylist
This article was co-authored by Stephanie Fajardo. Stephanie Fajardo is a Personal Stylist based in Portland, Oregon. Stephanie has over 17 years of styling experience in personal consulting, television, photography, and film shoots. Her work has been featured in Esquire Magazine and Portland Fashion Week. This article has been viewed 33,235 times.
15 votes - 84%
Co-authors: 9
Updated: February 22, 2022
Views: 33,235
Categories: Featured Articles | Dresses and Skirts
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