I Wear Sweater Dresses & Boots All Winter: Here’s 9 Ways To Change It Up

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I love jeans, but in the winter I usually want nothing to do with them. The thought of having to wear rigid denim in the cold is almost too much to bear.

I’m being *slightly* dramatic, but when it’s super-cold outside all I care about is being comfortable and, more important, warm. And I’ve found the best way to do this is to wear sweater dresses and boots…all. Winter. Long.

A Sweater Dress + Boots = My Fave Winter Outfit (9 Ways I’m Styling Them)

When it's cold, all I care about is being comfy & warm. I've found the best way to do this is to wear sweater dresses + boots.

coat | sweater dress | boots | bag

Sweater dresses are my go-to for winter outfits. They’re comfy, warm, and an easy way to look put together without actually having to think about it. And unlike jeans, I don’t have to overthink the whole boot-pairing situation. Moon Boots, UGG boots, Sorels, over-the-knee, ankle booties, lug-soled — they allll work with sweater dresses.

Shop Sweater Dresses I Love

I’m always on the hunt for a good sweater dress. There are a handful I love below, plus a recent article of mine where I tried seven sweater dresses under $100!

And when it’s really cold I can layer a pair of leggings underneath for added warmth (like my favorite Polartec leggings from Athleta).

Here’s how I’ve been wearing them this winter…

1. With Over-The-Knee Boots (& A Matching Bag) 

I've been wearing sweater dresses with ivory over-the-knee boots, & I'm loving the lighter look.

sweater dress | boots | bag

This look would no longer work in Marquette, Michigan’s frigid February, but it’s a perfect transition outfit for spring or fall. I typically layer a sweater dress over my all-time favorite undergarment/tank top/bra cami, Hanro’s Allure Bra Camisole (read all about how amazing that one is here), and boy-short undies or a bra and mini slip (this one’s my favorite) to keep things smooth.

This year I’ve been swapping my typical black boots and bags for ivory over-the-knee boots and love the lighter look.


2. With A Faux-Fur Coat & Lace Tights

If there are 2 pieces I need to have for my winter wardrobe, it's an amazing faux-fur jacket & a pair of lace tights.

similar coat | sweater dress | boots | bag

I mean…if there are two pieces I need to have for my winter wardrobe, it’s an amazing faux-fur jacket and a pair of lace tights. Faux fur makes everything better (and warmer!), and lace tights can be worn with sweater dresses, under distressed jeans, and with midi dresses to add a bit of warmth in winter.


3. With A Colorful Coat & Warm Moon Boots

I've tried all the winter/cold-weather/snow boots out there, & Moon Boots are by far the warmest shoes.

coat | sweater dress | boots | bag

Moon Boots are a must in frigid temps. I’ve tried alllll the winter/cold-weather/snow boots out there, and these are by far the warmest shoes I’ve ever worn. And I’ve been loving the colorful coat trends this year!


4. With Over-The-Knee UGGs & A Warm Puffer

I love this SAM. jacket, The stand collar, zip pockets, thumbhole cuffs, everything. (It runs small, so size up.)

sweater dress | jacket (M) | similar boots | bag

These Uggs are one of my most-worn boots of the winter — since first getting them in 2020. They no longer make this version, but I love the convertible UGG boots that can be worn three different ways (and they’re on sale!).

This SAM. jacket is also on sale — over $100 off! — and I LOVE it. The stand collar, zip pockets, thumbhole cuffs, everything. (It runs small, so size up.)


5. With A Long Faux-Fur Coat

A faux-fur coat — again. Adding a little length to my sweater-dress outfits lets me get away with bare legs.

similar coat | sweater dress | boots | bag

A faux-fur coat — again. Adding a little length to my sweater-dress outfits lets me get away with bare legs.


6. With A Long Faux-Leather Puffer & UGGs For Ultimate Warmth

The length of the faux-leather puffer coat, & the warmth of the UGG boots keeps the frigid temps at bay.

similar coat | sweater dress | similar boots

This is my go-to look for running errands or school pickup when it’s really cold out. The length of the faux-leather puffer coat, and the warmth of the UGG boots keeps the frigid temps at bay.


7. With A Statement Puffer & Wedge Boots

The color of this long puffer coat adds a bit of fun, & Sorel wedge boots are a bit sleeker — & equally as comfy.

similar coat | sweater dress | leggings | similar boots

A slightly dressier look, but it’s just as warm. The color of this long puffer coat adds a bit of fun, and Sorel wedge boots are a bit sleeker — and equally as comfy.


8. With A Flannel Button-Up & Leather Moto Jacket

When the weather isn't crazy cold, I like layering a flannel or button-up under a moto jacket to change things up a bit.

similar jacket | sweater dress | similar shirt | leggings | similar boots

When the weather isn’t crazy cold, I like layering a flannel or button-up under a moto jacket to change things up a bit. The sweater dress keeps things warm underneath.


9. With A Long Cardigan & Over-The-Knee Boots

similar cardigan | sweater dress | boots | tights | bag

I’ve been wearing this long cardigan SO much this year, I bought it twice. In the same color. I’ve found a maxi cardigan like this to be incredibly versatile, and it’s the perfect lighter layer for when the weather warms up a bit. And adding OTK boots over leggings keeps things warm and sleek.


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In conclusion…sweater dresses + boots, FOREVER.

XOXO,

Scotti

Sweater dresses. My go-to for winter outfits & so easy to style w/ boots (think: UGGs + Sorels, ankle + over-the-knee). Here are 9 warm ways I'm wearing them.

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