7 Pretty Fall Dresses to Put on With Boots and Call It a Day

One of the easiest outfits to transition us into fall is unquestionably a dress-and-boot combo. While we’ve been living in strappy sandals for the past few months, soon the leaves will be turning brown, the nights will be getting longer, and we’ll feel that crisp, cool air on our cheeks, finally signifying it’s time to get our limbs into something more toasty. Luckily, there are plenty of chic fall boots and dresses that are already making an appearance at some of our favorite retailers and getting us excited to shop for the new season ahead. To get us inspired, we found some chic dress-and-boot outfits that we fully plan on copying this fall. From mock-croc boots and luxe knit dresses to floral frocks and combat boots, scroll below for the simple striking dress-and-boot outfits to try this fall.

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A pretty pastel sweaterdress looks luxe with dark brown over-the-knee mock-croc boots. A cozy-meets-chic fall combo.

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Snake prints are one of the biggest trends for fall. Pair it with knee-high brown leather boots for a fashion-forward desk-to-drinks look.

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Pair a silky frock in this season's trending pistachio hue with tall cream boots, and lots of neutral layers for a refreshingly modern look that will take you from day to night in style.

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Add a cool-girl edge to a fun floral minidress with tactile and trending combat boots.

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Purple is the It color of fall 2019. Wear the color from head to toe as seen all over the fall F/W 19 runways.

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Lace-up ankle boots are trending hard for fall. Pair yours with a check dress—it's perfect for the office.

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Take your little white dress you've been wearing all summer into fall with the addition of chic croc-effect tall boots. 

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Sumptuous beige tones from head-to-toe make for one luxurious looking fall outfit. Pair a beige knit dress with trending snake-effect boots to take your neutrals to another level of chic.

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Up next, I found fall's chicest boots for under $150.

Judith Jones
Senior Fashion Market Editor

Judith is the senior fashion market editor at Who What Wear and has worked in fashion for nearly a decade. Judith started on the Shop Who What Wear team, creating content and managing a team of merchandisers for the Who What Wear shopping app. She later crossed over to the editorial team, where she shares the coolest, most desirable fashion market finds and brands in her shopping-focused stories and social takeovers. She has become one of the top affiliate earners during her six plus years at Who What Wear. Before working in fashion, Judith was a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) and shared her passion for travel and food. She studied at the prestigious London Academy of Dramatic Arts as well as Stella Adler Studio of Acting in New York. She later studied fashion merchandising and design, which laid the foundation for her career in fashion.


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