7 Outfits That Prove a Sweater Dress with Boots Is Perfect for Fall

No offense to beach days, snowy afternoons and spring showers, but sweater weather is the best. And while we’ll never get bored of pairing a cozy knit with jeans or leather trousers, there’s another cold-weather option that involves no pants at all: the beloved sweater dress. It’s easy to toss on, ridiculously comfortable, can be worn from work to drinks and looks flattering on all body types. Plus, when you add a pair of fall boots into the mix, you’ve got a timeless two-step outfit formula you can wear all the way through spring. Here are seven ways to wear a sweater dress with boots that will never go out of style.

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hm sweater dress with raid ankle boots

1. Maxi Dress + Knit Booties

Even if your maxi is made from a tighter, thinner knit, you’re still going to want to balance all that fabric with something a bit more svelte. A sock-like boot in a stretchy material adds a touch of sex appeal and flatters your stems. Bonus points if your knit booties have a pointy toe or stiletto heel.

Get the look: H&M dress ($50); RAID boots ($56)

Similar styles: Native Youth dress ($72); Generation Love dress ($178); Everlane boots ($155); Stuart Weitzman boots ($495)

paper london dress and marc fisher boots
The Outnet / Nordstrom

2. Curve-hugging Midi + White Booties

Printed knits in form-fitting silhouettes are perfect for keeping you comfy while still looking dressed up. Add a pop of bright white to keep things light and fun (as opposed to a black boot that might feel too heavy). It’s also best to opt for a structured boot or one that doesn’t cling to your ankle. You’ve already got the curve-hugging dress up top; be sure to balance it out by giving your calves and ankles a little breathing room.

Get the look: Paper London dress ($198); Marc Fisher Ltd. boots ($200)

Similar styles: ASOS dress (45$); Opening Ceremony dress ($194); Taryn Rose boots ($147); Sam Edelman boots ($180)

oversize sweater dress with flat over the knee boots
Aritzia / Shopbop

3. Oversize Sweater + Flat Over-the-knee Boots

This might be our favorite of the sweater dress styles because it’s supremely forgiving and ideal for those days when you really just can’t deal with pants. That said, providing some coverage for your stems is key here, which is why thigh-highs make for such a great match. Stick to flat boots or a chunky one- to two-inch heel for day, and feel free to add on a pair of tights that are just sheer enough to differentiate from your suede boots.

Get the look: Wilfred dress ($178); Stuart Weitzman boots ($798)

Similar styles: Lulus dress ($43); Tularosa dress ($160); ASOS boots ($64); Vince Camuto boots ($179)

crochet dress with western booties
The Outnet / Nordstrom

4. Loose Knits + Western Inspired

Open weaves, like crochet, are inherently more casual. Pairing them with edgy black, suede thigh-highs or Mod, pointy-toe white booties is too disparate and won’t look cohesive. But a classic brown or tan cowboy boot? Now that feels right. A Western bootie, besides being very trendy right now, will match the low-key aesthetic of your frock.

Get the look: Alexa Chung dress ($247); Sam Edelman boots ($180)

Similar styles: Eleven Six dress ($158); A.L.C. dress ($279); Missoni dress ($1,295); Matisse boots ($90); Villa Rouge boots ($225)

cardigan dress and moto boots
Orchard Mile/Dr. Martens

5. Long Cardigan + Combat Boots

Offset the preppy (and slightly sexy) nature of an extra-long cardigan by wearing it with some tough combat boots. Opt for pairs with a lower shaft and slimmer sole to avoid looking too ’90s grunge. (Bonus points if you also try boots that are burgundy, navy or even white instead of the go-to black.)

Get the look: Equipment dress ($350); Dr. Martens boots ($174)

Similar styles: Eloquii dress ($130); Naadam dress ($250); Crown Vintage boots ($70); Frye boots ($198)

jcrew and lucky brand
J.Crew / Neiman Marcus

6. Knit Dress + Hem-grazing Boots

Not quite a sweater, but heavier than your average day dress, this pleated knit is a fabulous way to stay warm and stylish through the colder months. Just make sure to select boots that won’t leave any of your leg exposed to the elements. Stick to suede over-the-knee styles or trendy snake-print riding boots that just meet the hem of your dress.

Get the look: J.Crew dress ($138); Lucky Brand boots ($219)

Similar styles: Gal Meets Glam dress ($158); Kate Spade New York dress ($160); Treasure & Bond boots ($150); Naturalizer boots ($235)

rebecca taylor sweater dress with blouse and boots
Orcahrd Mile / Nordstrom

7. Sleeveless Knit + Long-sleeve Blouse + Pointy-toe Boots

At first the idea of a sleeveless dress in a warm wool doesn't make all that much sense. Rather than wasting time trying to make sense of this summer/fall hybrid, simply match them up with a gorgeous long-sleeve blouse. (We prefer one with billowing sleeves, an intriguing detail at the neck or a contrasting pattern for an extra pop of interest.) The end result? A '70s inspired nod to back-to-school style. Pointy-toe boots will help keep you looking like an adult, rather than a kid playing dress-up.

Get the look: Rebecca Taylor dress ($130); 1.State blouse ($79); Vince Camuto boots ($150)

Similar styles: Elisabetta dress ($40); MICHAEL Michael Kors dress ($88); Moon River blouse ($65); A.L.C. blouse ($160); BP boots ($80); Schutz boots ($245)



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...