A woman wearing an ENGLISH FACTORY black faux leather shift dress and knee-high black boots holds a small red handbag, showcasing impeccable fall dress styling. She has long, dark hair and is standing against a neutral background.

ENGLISH FACTORY

The Dress Edit

I’m A Fashion Editor, These Are My Top 5 Fall Dress Styling Tips

Looking for flawless fall dress styling tips now the new season is officially here? You’re in the right place. As a fashion editor,  I’ve nailed down the fall styling tips that work with dresses every single time. So, whether you’re planning your new season weekend outfits or a special occasion ensemble, this specially selected edit of dresses has just what you need. Keep scrolling for new-season styles from Veronica Beard, English Factory, Free People, and more…

A woman stands in a harvested field beside a large bale of hay, showcasing her fall dress styling. She is wearing the DÔEN Coraline brown silk midi dress with floral detailing and has long blond hair. The sky is clear and blue, with a line of trees in the background.

DÔEN Coraline Dress

A woman wearing the DÔEN Jessica black and white midi dress, perfect for fall styling, leans against a stone railing by the river. The background reveals a historic building and a vibrant sunset sky with scattered clouds. She has long dark hair and is smiling.

DÔEN Jessica Dress

Fall Dress Styling Tips For Midi Dresses

As soon as the cooler weather hits, I start using my favorite dress styling tips for midi and maxi dresses. Luckily, they go so perfectly with my go-to footwear at this time of year that accessorizing these versatile silhouettes couldn’t be simpler.

Tip One: Add Flats Instead Of Heels For A Classic Day To Night Look

Heels are great for summer and, of course, can work in fall too. However, I’ve always found that designer flats are the perfect shoe option for this time of year. The weather feels too cool for open-toe heels and intermittent showers make stiletto pumps a no-go. Therefore, I’ll be styling dresses like the Jessica dress by Dôen with the Mamastrapitina ballerina flats by Christian Louboutin. Throw your essentials inside the eternally stylish Intrecciato concert pouch by Bottega Veneta to complete your day-to-night look.

Tip Two: Boots & Knitwear Work Every Time

Adding a fall touch to a midi dress is as simple as chunky knitwear and a great pair of designer boots. Additionally, try contrasting textures to add interest to your outfit with a chunky knitted sweater and a silky dress. Speaking of which…

Tip Three: Elevate Your Closet With Silky Dresses In Autumnal Shades

Try the gorgeous, deep brown hue of the Coraline dress, also by Dôen. Add the Vlogo Moon pointed slingback pumps by Valentino Garovani and the mini Andiamo bag by Bottega Veneta. Finally, throw a lightweight, structured jacket over top for the quintessential pre-winter weekend look.

Shop more Fall Dress Styles selected and reviewed by our expert fashion buyers and stylists

  • ENGLISH FACTORY Faux-Leather Mini Shift Dress

    $90
  • ENGLISH FACTORY Scallop Mini Shift Dress

    $140
  • HUTCH Velvet Shift Bow Mini Dress

    $178
  • AFRM Kay Long-Sleeve V-Neck Mesh Maxi Dress

    $128
  • AFRM Hazel Bare Mesh Midi Dress

    $78
  • VERONICA BEARD Isra Silk Dress

  • VERONICA BEARD Nami Sweater Dress

  • ISABEL MARANT Albini Gathered Printed Silk-Blend Midi Dress

    $1,390
  • FREE PEOPLE Sunkissed Mini Dress

    $168
  • FREE PEOPLE Freya Floral Mini Dress

    $198
  • FREE PEOPLE Hampton Mini Dress

    $168
  • FAITHFULL Paloma Open-Back Silk-Voile Maxi Dress

    $500
  • ULLA JOHNSON Celia Pleated Paisley-Print Wool-Blend Twill Midi Dress

    $750
  • RABANNE Pintucked Embroidered Lace Maxi Dress

    $1,302
  • SIR. Aries Square Neck Lace Slip

    $520
  • SIR. Aries Cut Out Gown

    $520
  • VICTORIA BECKHAM Gathered Midi Dress

    $1,250
  • ANTHROPOLOGIE Sheer Lace Tunic

    $130
  • L’ACADEMIE Marianna Izel Mini Dress

    $208
  • LPA Fallon Sweater Dress

    $148
  • ANTHROPOLOGIE Tommie Front-Zip Shirt Dress

    $170
  • DÔEN Katarina Dress

    $398
  • DÔEN Coraline Dress

    $448
  • AJE Cohort Mini Dress

    $455
  • ULLA JOHNSON Gemma Broderie Anglaise Cotton-poplin Mini Shirt Dress

    $490
  • DÔEN Jessica Dress

    $548
  • BALENCIAGA Ribbed-knit Turtleneck Maxi Dress

    $2,790

Timeless Fall Dress Styling Tips For Classic Silhouettes

For me, successful fall dress styling is all about finding classic silhouettes, shoes, and accessories, you’ll want to wear for years to come. In other words, pieces worth investing in.

Tip Four: Choose Dresses, Bags, & Shoes You’ll Wear This Season And Beyond

Dresses like the Hazel bare mesh midi by AFRM, therefore, are perfect. Firstly, the black and white polka dot design will never go out of style. Secondly, versatile, monochrome shoes and bags will work with it every time. Therefore, I highly recommend adding this dress to your cart, along with the Bluebell clutch by Clio Peppiatt, and the Seraphine pumps by Gucci.

Tip Five: Make Boots & Slip Dresses A Staple Outfit

Boots and slip dresses are a match made in heaven for fall RSVP’s. Top of my must-have list this fall? The Aries gown by SIR., the Santia knee-high boots by Christian Louboutin, and the Vela bag by Etro.

Shop All Fall Dress Styles

A person stands outdoors with eyes closed and arms gracefully posed around the head. The individual is wearing the SIR. Aries brown silk and lace slip dress 2, bathed in sunlight. This elegant display of fall dress styling perfectly complements the blurred nature setting in the background.

SIR. Aries Cut Out Gown

A person dressed in the AFRM Hazel mesh black and white polka dot dress crouches on the ground, showcasing impeccable fall dress styling. They are wearing white pointed-toe shoes with a low heel and buckle detail. The individual rests one hand on their knee while lightly touching their head with the other.

AFRM Hazel Bare Mesh Midi Dress

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