3 Ways to Style a Midi Dress This Fall

Bows & Sequins wearing a floral midi dress with a black hat, a leather Madewell belt, and black ankle booties with a Brahmin bag.

Whenever the weather starts to transition to fall, I’ve realized I always opt for denim. Jeans are easy, they’re comfortable, they’re flattering, and they go with just about everything… What’s not to love?! But since we’ve gotten lucky with a very warm fall so far (and I’m sure I’ll be living in denim all winter long), I’ve been making an effort to spice things up with dresses and skirts these past few weeks.

Bows & Sequins wearing a Blank NYC suede jacket with an Old Navy fall floral midi dress and Marc Fisher purple velvet booties.

I picked up this floral midi dress a few weeks ago at Old Navy and I’ve already worn it a handful of times! There’s a common conception that skirts and separates are the most versatile, but when you’ve got yourself a dress that can be styled so many different ways, that’s not always the case. The best dresses are ones you can wear over and over with different layers and accessories for unique looks!

Bows & Sequins wearing a Blank NYC cognac suede jacket and aviators.

1. Suede Jacket + Colorful Accessories

The colors in this floral pattern are basically fall in a nutshell, which maximizes versatility! Mustard yellow, cognac brown, a deep red, and dark green all rooted in black. For this first look, I played up all of the different colors with mixing them all into one outfit. The key to doing this is choosing a variety of textures! Dark purple velvet booties, a rich suede chestnut-colored jacket, a green crinkled leather bag, and a little pop of bordeaux red with a thin suede belt. It’s a lot going on, but I think it’s a fun boho look for brunching on the weekend or heading out to dinner!

Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, a Joelle Hawkens green leather shoulder bag, Marc Fisher purple velvet booties and Ray-Ban aviators.

Get the Look…

Old Navy Floral Midi Dress
Blank NYC Cognac Suede Jacket (similar style at Old Navy!)
Old Navy Suede Burgundy Belt
Marc Fisher Purple Velvet Booties
Joelle Hawkens Green Leather Bag (similar style at Old Navy!)
Gucci Aviator Sunglasses

Jessica from Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, a Joelle Hawkens green leather shoulder bag, Marc Fisher purple velvet booties and aviators.

Bows & Sequins wearing aviators, a black cardigan, floral midi dress, and pink glitter sneakers with a Polene top-handle leather bag.

2. Slouchy Sweater + Sneakers

If you’re looking for a more casual way to wear this dress, you can’t go wrong with a slouchy sweater and a fun pair of sneakers. Oversized, cozy cardigans are all the rage this fall, but I feel like our first instinct is to just pair them with skinny jeans and booties. I love the juxtaposition you get when wearing them with something more feminine, like a dress or a skirt!

Bows & Sequins wearing matte aviators, a black cardigan, and an Old Navy floral midi dress.

Get the Look…

Old Navy Floral Midi Dress
Old Navy Cardigan
Tretorn Glitter Sneakers (similar style at Old Navy!)
Polene Leather Top-Handle Bag (similar style at Old Navy!)
Le Specs Matte Black Aviators

Bows & Sequins wearing a floral dress and Tretorn pink glitter sneakers.

Chicago lifestyle blogger Bows & Sequins wearing matte aviators, a long black cardigan, floral midi dress, and pink sneakers.

Chicago style blogger Bows & Sequins styling a floral midi dress from Old Navy with a black hat, black leather Madewell belt, and ankle booties.

3. Hat, Belt, & Booties

For a more classic look, pair your fall midi dresses with tonal accessories, like a hat, leather belt, booties, and a structured bag! Perfect for the office (maybe minus the hat), meetings around the city, dinner with the girls, or even grabbing drinks after work.

Bows & Sequins wearing an Old Navy hat, a floral print dress, Kate Spade watch, Madewell leather belt, and ankle booties.

Get the Look…

Old Navy Floral Midi Dress
Old Navy Hat
Madewell Black Leather Belt (similar style at Old Navy!)
Steve Madden Black Ankle Booties (similar style at Old Navy!)
Brahmin Leather Bucket Bag (similar style at Old Navy!)
Kate Spade Watch
Ray-Ban Aviators (similar style at Old Navy!)

Jessica Sturdy of Bows & Sequins wearing a black hat, black Madewell leather belt, and ankle booties with a Old Navy floral midi dress.

Bows & Sequins wearing a black hat from Old Navy, a floral dress, and a tan leather Brahmin bucket bag.

Bows & Sequins wearing an Old Navy fall floral midi dress with a Madewell leather belt, black hat, a Kate Spade watch, and ankle booties.

Chicago style blogger Bows & Sequins wearing a black hat, a floral midi dress, a Madewell leather belt, and a Brahmin bucket bag.

4, 5, 6, 7, 8, 9, 10 … you get the idea!

Think outside the box… Try on your fall dresses with your denim jackets, vests (faux fur, black, white, army green, etc.), layer a turtleneck and tights underneath, dress it up with a pair of pumps for work, wear with ankle booties, try them with ballet flats. Have fun with it!

Bows & Sequins wearing Gucci aviators, a Blank NYC cognac suede jacket, a floral midi Old Navy dress, and purple velvet booties.

Oh, and just a little tip for sizing… I’m usually a small in Old Navy this season, but they were sold out of smalls in this color when I was shopping. I tried on the XS and it actually fit, so I’d size down if you’re in between sizes!

Bows & Sequins wearing a floral dress and Tretorn pink glitter sneakers.

Bows & Sequins wearing an Old Navy hat, a floral print dress, Kate Spade watch, and Madewell leather belt.

Here are a few more great midi dresses from Old Navy…

Bows & Sequins wearing matte aviators, a black cardigan, floral Old Navy midi dress, and Tretorn pink sneakers with a Polene top-handle leather bag.

Bows & Sequins wearing a floral midi dress and Marc Fisher purple velvet booties.

Fashion and style blogger Bows & Sequins wearing a Blank NYC cognac suede jacket and Joelle Hawkens green leather shoulder bag.

Bows & Sequins wearing a black hat, a floral midi dress, a black leather Madewell belt, black booties, and a Brahmin leather bag.

Chicago blogger Bows & Sequins wearing a black cardigan and a floral midi dress with a top-handle Polene bag and pink glitter sneakers.

Chicago fashion and style blogger Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, a Joelle Hawkens green leather shoulder bag, Marc Fisher purple velvet booties and aviators.

Bows & Sequins wearing a black Old Navy hat, a floral dress, and a Brahmin leather bucket bag.

Bows & Sequins wearing matte aviators, a black cardigan, and a floral midi dress with pink glitter sneakers.

Bows & Sequins wearing a black cardigan, floral midi dress, and pink glitter sneakers with a Polene leather top-handle bag and aviators.

Bows & Sequins wearing Le Specs matte aviators, an Old Navy cardigan, floral dress, and a black leather belt.

Chicago blogger Bows & Sequins wearing a black hat, Ray-Ban aviators, a floral midi dress, a black leather belt, and ankle booties.

Bows & Sequins wearing a floral Old Navy midi dress with black accessories.

Bows & Sequins styling a cognac suede jacket and floral dress.

Bows & Sequins wearing a black hat, an Old Navy midi dress, a black Madewell belt, and ankle booties.

Fashion and lifestyle blogger Bows & Sequins wearing a floral midi dress with a black cardigan, a black belt, and pink glitter sneakers.

Jessica from Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, a Joelle Hawkens green leather shoulder bag, Marc Fisher purple velvet booties and aviators.

Chicago style blogger Bows & Sequins wearing a black Old Navy hat, a floral midi dress, a black Madewell leather belt, and ankle booties.

Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, Marc Fisher purple velvet booties and aviators.

Bows & Sequins wearing a long black cardigan, a floral midi dress, glitter sneakers, and a Polene top-handle leather bag.

Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, a Joelle Hawkens green leather shoulder bag, a burgundy belt, Marc Fisher purple velvet booties and aviators.

Jessica from the fashion-focused lifestyle blog Bows & Sequins wearing an Old Navy black hat, aviators, a floral dress, black Madewell belt, and a Brahmin leather bag.

Chicago lifestyle blogger Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, a Joelle Hawkens green leather shoulder bag, Marc Fisher purple velvet booties and aviators.

Jessica from Bows & Sequins wearing a Blank NYC cognac suede jacket, an Old Navy floral midi dress, a Joelle Hawkens green leather shoulder bag, Marc Fisher purple velvet booties and aviators.

Bows & Sequins wearing matte aviator sunglasses, a black cardigan, and a floral midi dress from Old Navy for fall.

Fashion and travel writer Bows & Sequins styling a Blank NYC cognac suede jacket with an Old Navy floral dress and aviators for fall.

Bows & Sequins wearing a floral dress with a black leather belt, black ankle booties, Ray-Ban aviators, and a Brahmin leather bag.

Bows & Sequins wearing a suede jacket with a floral midi dress and a green leather shoulder bag.

Fashion and lifestyle blogger Bows & Sequins wearing a black Old Navy hat, Ray-Ban aviators, and a floral dress with a Brahmin leather bag.

Chicago style blogger Bows & Sequins wearing a cognac suede jacket, an Old Navy floral dress, and purple velvet Marc Fisher booties.

Bows & Sequiins wearing a black Old Navy cardigan, a midi floral dress, and Tretorn pink glitter sneakers with a top-handle black leather handbag.

Chicago style blogger Bows & Sequins wearing a cognac suede jacket, an Old Navy floral dress, and purple velvet Marc Fisher booties.

Bows & Sequins wearing a black hat, an Old Navy floral dress, and a Brahmin leather bag.

Chicago lifestyle blogger Bows & Sequins wearing a cognac suede jacket, a floral Old Navy dress, and Marc Fisher purple velvet booties.

Chicago fashion blogger Bows & Sequins wearing a black cardigan, fall floral midi dress, and glitter sneaker with a black leather handbag.

Jessica of the fashion-focused blog Bows & Sequins, wearing a black Old Navy hat, matte aviators, a black leather Madewell belt, and ankle booties with her Old Navy fall floral dress.

Created in partnership with Old Navy

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7 Comments

  1. 10.18.17

    I always get content this time of year and constantly reach for my jeans, but I’ve been trying to switch it up too and wear all my dresses and skirts. I love that it’s been so mild in the Midwest! That floral dress looks so good on you and I love how you styled it!

  2. 10.18.17
    Natali commented:

    Such a pretty boho and very versatile floral dress! Love the way you’ve styled it differently here. 🙂

    https://lartoffashion.com

  3. 10.18.17
    Kate commented:

    I wish I could do pull of midi dresses. They just look awkward on me sadly
    Kate || KATE KOUTURES

  4. 6.19.18
    Jill Troughton commented:

    Such a pretty and very versatile floral dress! Love the way you’ve styled it differently here. I loved it. I also wear midi dress but in denim I mean I like to wear denim midi dress mostly.Its also look so beautiful and stylish.