12 Stylish Ways to Wear Sweater Dress with Boots

Gabi Fresh sweater dress and boots

I’m looking for some fashion inspiration for the Fall and Winter months, and lately I have been drawn to sweater dresses paired with knee-high or over-the-knee boots. There are dozens of ways to wear sweater dresses and boots separately, but there are just as many ways to style these two pieces together.

I have a sweater dress, but it hits below my knees. I actually featured my sweater dress on my dress form a few years ago. Even though this dress is several years old, I can still style this for Fall.

Just remember that picking the right sweater dress {style, shape, or color) is just as important as picking the right boots {knee-high or over-the-knee} to wear with your dress. So here are 12 stylish ways to wear a sweater dress with boots. 

If you want to go with a monochromatic look, like these all-black looks, then pair an oversized sweater with knee-high or over-the-knee boots is so stylish. Two different looks, but both are slightly sexy in their own way.

sweater dress with boots 4

{Images borrowed from 1 // 2}

I also like these pretty winter whites paired with OTK books – one paired with brown boots and the other with black boots. I also love how they accessorized their outfits – one with a Louis Vuitton notebook/planner and a cuddly little dog and the other with a plaid scarf, a hat, and an oversized purse.

sweater dress with boots 5

{Images borrowed from 1 // 2}

These two ladies have the same casual stance, as if they are waiting for someone, when in fact they are perfectly posed to highlight their lovely legs. I love the black turtleneck sweater dress paired with the thigh-high boots, and I also love the monochromatic gray sweater dress paired with the suede OTK boots. But what I really love is that pairing a sweater dress and boots looks great on every shape and size.

sweater dress with boots 3

{Images borrowed from 1 // 2}

Choosing the right pair of boots – whether they are knee-high boots or OTK boots – is just as important as picking the right sweater dress. For instance, the brown boots come up to the knees, but they are open behind the knees to allow some flexibility when walking or sitting. This style boot is comfortable for women who don’t want a tight-fitting boot to come up over their knees. The burgundy boots look like they lace up or possibly tie at the top, behind the lower thighs, which give these boots some sex appeal. This style boot is perfect for women who want to highlight their legs.

sweater dress with boots 1

{Images borrowed from 1 // 2}

When the weather turns colder, you may want to layer a long vest {like Jamie Chung, left} or a lightweight jacket {like Nadia Aboulhosn, right} over your sweater dress.

sweater dress with boots 2

{Images borrowed from 1 // 2}

Pairing a heavier coat with a monochromatic outfit, like the one pictured below, is such a classy look, and perfect for a date night. I like the look of suede boots {over leather boots} with a sweater dress, but that’s just my preference.

sweater dress with boots fi

{Image borrowed from Trend 2 Wear}

So now that we have some fashion inspiration for pairing sweater dresses with boots, here are some styling tips on how you can pull off this look for Fall and Winter.

  1. Belt it. Some sweaters are loose and bulky, which hide your waist. Belting it, whether it’s with a wide or skinny belt or an obi belt, cinch it in to show off your figure.
  2. Wear leggings or skinny jeans, especially when the weather gets colder.
  3. In the meantime, wear socks that peek out from the top of your boots or try opaque tights.
  4. Try a turtleneck or a cowl neck sweater dress.
  5. Try wearing over-the-knee boots for a sexier vibe.
  6. Drape a blanket scarf, poncho, or a jacket over a sleeveless sweater dresses.
  7. Wear a long statement necklace to give your outfit a boho vibe.
  8. Accessorize. Wear a hat or sunglasses for a more street style look.
  9. Top a fitted seater dress with a vest for a winter look.
  10. For a preppy look, wear a button down shirt under your sweater dress, with the collar and cuffs peeking out, and then add a statement necklace for special occasions.

Model Gabi Fresh looks amazing in her sweater dress with over-the-knee boots. She kept her look simple and monochromatic, but yet, she looks beautiful and sexy. This just goes to show us that style has no size.

Gabi Fresh sweater dress and boots

{Image borrowed from StyleCaster}

Do you plan on rocking this look this Fall? Finding the right sweater dress and the perfect pair of boots can be tricky, but wear what you feel comfortable in and style it your way!

Yours Truly,

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