How To Style Sweater Dresses

December 10, 2023

Sweater Dress Styled I wit & whimsy

It’s sweater dress season! I love this window in time of the year where you can wear a sweater dress, no tights required and today I am sharing a few looks at how I style my sweater dresses for Fall. I hope you’ll find these inspiring as you style your sweater dresses in the coming months.

How To Style Sweater Dresses

The sweater meets the dress = sweater dress. Cozy, comfy and totally versatile, I love having a few sweater dresses on rotation each Fall. I also tend to pull some of them back out in the Springtime when the weather begins to warm up again and I pair them with a denim jacket or one of my favorite trench coats.

I think a sweater dress is a wardrobe staple. And I like how versatile they are when it comes to making them your own – pair with combat boots or dress them up!

I love the ability to dress up or dress down a sweater dress and all the different styles they come in – from turtleneck styles to midi or mini dresses. So many options nowadays with cute balloon sleeves or ruffled collars, etc. They are also the perfect building block to stay warm but still look cute when the weather is cold out.

At the bottom of the post I have rounded up some favorites of mine that are currently available. 

Sweater Dress Styled I wit & whimsy

Sweater Dress Styled with Leather Jacket and Ankle Boots I wit & whimsy

With a Leather Jacket and Ankle Boots

We all know dresses and boots are a match made in heaven all of Fall and Winter.

The way I most frequently wear my sweater dresses is with ankle boots with a heel for some height and then topped with a leather jacket. I find topping it with a jacket makes me feel less self conscious than I can sometimes for sweater dresses that may not have the most flattering fit or fabric. Instead of swearing it off, adding a cropped jacket can be just the answer.

Able Sweater Dress Styled I wit & whimsy

Add a Belt

Adding a belt in a contrasting or similar color of a sweater dress is a great way to give your waist added definition or add visual interest to a more plain outfit. Or you can look for a sweater dress that has a built in belt!

I like that this sweater dress by Able comes with a belt for a slimming effect and some added versatility.

Sweater Dress Styled I wit & whimsy

Neutral Tones and Knee High Boots

Neutral Tones and Knee High Boots

I love how a sweater dress looks when paired with knee-high boots. I topped this pretty brown sweater dress from Amazon with a similar-color coat for a monochromatic look up top. Also, I love tonal dressing so I added a bag in the same hue, too.

Over the Knee Boots winter outfit

With Over the Knee Boots

Flat or heeled, a shorter sweater dress pairs beautifully with an over the knee boot.

Similar dress style here.

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With Sneakers

I love a midi sweater dress mixed with a clean white sneaker for a more sporty take.

cashmere sweater dress

In Cashmere

Level up the sweater dress by picking a style in sumptuous cashmere. This one has a pretty boatneck neckline and I love the ribbed waist accent that makes for a flattering fit. I’m wearing a size M and paired it with these boots.

What To Wear Over A Sweater Dress

What To Wear Over A Sweater Dress

I’m all about layering this time of year so adding a classic overcoat over a sweater dress is a timeless way to take it from day to night.

Everlane Cashmere Turtleneck Dress I wit & whimsy

I especially love doing this over a turtleneck sweater dress like the above style.

Seen with these boots.

See my Favorite Winter Coats for Women.

Sweater Dress Outfit

How To Dress Up A Sweater Dress

Sweater dresses can be easily dressed up with the right shoe and coat but I also think a very chic way to dress up a sweater dress is to dress monochromatically. So add accessories in the same color scheme as your sweater dress for an instantly elevated, expensive look.

Above I am wearing this sweater dress from Amazon in a size L. Looks way more expensive than Amazon styled this way, am I right? I just ordered this style, too as I love the flared sleeve!

Look to accessories as well for dressing up a sweater dress. You could add a scarf, some great earrings or a really fun bag as well.

Go off the Shoulder

Another way to dress up a sweater dress is to get an off the shoulder style. It’s a perfect style to make sweater dresses appropriate for date nights! I’ve linked a variety of this style that I like below. I like this under $100 one in particular.

Add Texture

A great way to add visual interest to any look is to add texture and sweater dresses are perfect for this because so many of them come in great cable knit or ribbed knit textures. 

Try a Wrap Style

A wrap dress in knit can be a beautiful way to have a dressier sweater dress. 

Play with Proportions

Styling a shorter sweater dress? Instead of knee high boots, you could add a calf boot. I love mixing and matching proportions when styling sweater dresses.


Consider adding a collared shirt under your mini sweater dresses.

Nail your Sizing

I tend to order more than one size of sweater dresses because I want the fit to be perfect. Too big and you risk adding bulk to your frame. Too small and I’ll be left feeling like I want to add a pair of spanx.

. . .

Do you have any favorite ways to style a sweater dress?

And might I recommend wearing high waisted underwear like this? I swear by it under sweater dresses to make everything lay a bit more smoothly! If you’re in between sizing I recommend sizing up.

Shop Sweater Dresses

Below I’ve curated the best sweater dresses available to shop now. All at a variety of price points!



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comments +

  1. Hannah says:

    Loved this post! Thank you for sharing your ideas for sweater dresses. I can’t wait to give some a try. As always, a visit to your blog is such a joy and your hard work is so appreciated. Have a wonderful rest of your week!

  2. Kristin says:

    Looks pretty! I’ve been loving sweater dresses for years and <3 that they're so in right now. Seems like jewelry is essentially nonexistent for most of them (and not just on your page)…is that the trend you're noticing?

    Also, my own stupid gripe – living in the northeast, most of the joy of sweater dresses for me is WARMTH, so all of the bare legs that are part of the styling of sweater dresses is hard for me to compensate for!

  3. Each and every combination is so beautiful. You are looking magical!

  4. Hope says:

    Oversized sweater is better to match with boots…looks very sexy. However, there are not so many options when it comes to petite. Any recommendations? Thanks

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