How to Wear Dresses in Fall: 10 Ways To Wear Dresses This Season

As the cooler weather of autumn approaches, it’s time to transition your wardrobe from summer staples to cozy fall outfits that still have a sense of style and charm. 

Finding fabrics that are breathable yet warm and figuring the right layers to wear with different style dresses is crucial to celebrating your style throughout the season.

But does it mean you have to go and buy a whole new wardrobe full of trend driven pieces?… Not at all.

While you might think summer dresses are only for warmer months, with a few simple styling tricks, they can easily transition into the perfect dress for your fall wardrobe. 

In this article, we’ll guide you through the best dress outfits for fall that will help you stay warm without sacrificing style or making you look frumpy.

Whether you’re looking for fashion inspiration or simply want to know how to extend the life of your favorite summer dress, we’ve got the tips to keep you looking fabulous this autumn!

Pro Tip: Pin your favorite looks to your Pinterest boards for style inspiration

1. Layer with Knitwear

Layering with knitwear is an easy way to transition your dresses into fall.

Combine a lightweight dress with an oversized sweater and belt it at the waist for a flattering, cinched silhouette that’s ideal for early fall layering.

Pair an textured chunky sweater with a long floral maxi dress for a cozy yet chic look.

Style a silky slip dress under a cashmere sweater for added warmth while maintaining a polished look.

A shirt dress works well for layering under more fitted knits—let the shirt collar peak out the top of your sweater and roll back the sleeves for a casual, relaxed vibe.

2. Incorporate Heavier Footwear

Heavier footwear adds both style and extra warmth to your fall dresses.

Opt for loafers or laced up oxford shoes with socks for a polished, preppy style when a full boot isn’t necessary.

Pair a midi dress with knee high boots for a sleek look that offers full coverage and warmth.

Style a midi dress with ankle boots like a smart Chelsea boot for a balanced, laid-back vibe perfect for daytime outings.

Wear tall boots that hit above the knee with a short dress to add structure and keep your legs warm as temperatures cool.

3. Cozy Up with Leggings & Tights

Tights can be a stylish way to extend your wardrobe into the colder months.

Layer patterned tights under simple dresses to add texture and interest to your look.

Use colored or patterned tights to make a statement while transitioning your lighter summer dresses into the fall.

Pair neutral dresses with legging or jeggings and sneakers for a super practical yet cute look that will get you through a busy day.

4. Use Scarves and Shawls to Your Advantage

Scarves and shawls are versatile accessories that add extra coziness to fall outfits.

Add a colorful statement scarf to a neutral dress to bring warmth and personality to your outfit.

Drape a large scarf or poncho over your shoulders for a blanket-like effect that pairs well with a fitted dress.

Wrap a lightweight textured shawl around a midi dress for a soft, layered look perfect for cooler evenings.

5. Select Seasonal Fabrics, Prints, Colors & Textures

Choosing the right fabrics and colors helps create a cohesive fall wardrobe.

Swap out light summer cottons for seasonal fabrics like cashmere, knits, wool, velvet, and corduroy which add both warmth and a fall-ready look.

Opt for rich, earthy tones like burgundy, olive, and mustard to complement the season.

Opt for accessories like a leather bag or printed scarf to add subtle texture and pattern to a simpler outfit.

Pair a floral dress with a plaid scarf or jacket for a fun contrast that blends feminine and classic fall patterns.

6. Pair With a Statement Jacket or Blazer

A statement jacket or blazer can instantly elevate your fall dress looks and make them look more complete.

A leather or moto jacket gives a edgy contrast when worn over a dress that has a more floaty or feminine material like lace or chiffon.

A denim jacket adds a casual rustic touch that goes great with natural fabrics like cotton or linen, making it easy to transition summer dresses into the cooler months.

Pair a structured blazer with a midi dress for a polished look or a more casual boyfriend blazer vibe that works well for both day and evening.

7. Belt Outer Layers

Belting outer layers can transform your fall outfits by adding shape and style.

Belt an oversized poncho or cape for a stylish, fall-ready look that adds definition and keeps your layered outfit from feeling too loose or shapeless.

Cinch a classic trench coat with a statement belt for a sleek, sophisticated look that highlights your waist.

Add a belt to a wool coat or cardigan for added structure, preventing bulky layers from overwhelming your silhouette.

8. Layer Underneath

Layering underneath your dresses is a smart way to extend their wearability into fall.

Experiment with layering tips like mixing textures and contrasting colors to add dimension and personality to your look.

Wear a long-sleeve tee under a strapless or a sleeveless dress for added warmth and style.

A turtleneck underneath a slip or shirt dress offers both comfort and a polished, layered look.

Use T-shirts or a button-up top as base layers under lighter dresses, creating easy fall outfits.

9. Accessorize with Jewelry, Hats & Seasonal Touches

Jewelry and hats are a great way to complete your fall dress outfits while adding your own personality.

Try a newsboy cap with a blazer and dress combination for vintage-inspired touch.

Pair a wide-brimmed fedora hat with a flowy dress for a boho-inspired look perfect for early fall.

Use layered bracelets or cuffs to accessorize dresses with long sleeves, drawing attention to your wrists.

Pair chunky gold or silver statement necklaces with high-neck dresses or turtlenecks for a bold look.

10. Opt for Long Sleeve or Sweater Dresses

Long-sleeve and sweater dresses are a great outfit base for fall and they’re ideal for staying cozy while looking chic and in tune with the season.

You can go for a simple sweater dress with minimal accessories and let the texture the knitted fabric do the talking.

Knitted dress in light or neutral tones work the best so that the texture detail is more visible and stiking.

Choosing thick or cable knitted dresses with long sleeves will help to keep you warm without needing too many extra layers which are perfect for transitional autumn days.