How To Style Sweater Dresses - Wit & Whimsy

In my book it is officially sweater dress season. Today I am sharing a few looks at how I style my sweater dresses for Fall and 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. But styling is key – otherwise you run the risk of looking quite frumpy.

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.

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. Just make sure the ankle boots hit you at a point on your leg that doesn’t cut you off too much making you look shorter than you are.

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.

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!

Styled with these 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.

With Over the Knee Boots

Flat or heeled, a shorter sweater dress pairs beautifully with a pair of Stuart Weitzman boots.

The brand La Canadienne has a lot of boots that are waterproof which is brilliant for fall and winter’s unpredictable weather.

Similar dress style here and here.

With Sneakers

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

In Cashmere

Level up the sweater dress by picking a style in sumptuous cashmere. I paired mine from last year with these boots.

Wearing the same boots with this great Amazon sweater dress (size L). I ordered the similar maxi style, too recently.

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.

See my Favorite Winter Coats

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

Seen with a pair of Stuart Weitzman boots.

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?

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 one in particular.

Add Jewelry

Sweater dresses are perfectly primed for adding statement necklaces or some pretty earrings.

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.

Layer

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.

Or consider having the sweater dress tailored – particularly with the length so that it hits you at exactly the right spot.

Go Tonal

Pick a color palette and dress all in corresponding shades. It’s an easy way to look like you’re dressed expensively.

. . .

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

And might I recommend wearing high waisted underwear like this or shaperwear shorts like these? I swear by them 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!

You May Also Like:

• A Fall Capsule Wardrobe.
• A Roundup of My Favorite Boots and Booties.
• Budget Friendly Outfit Inspiration for Fall.

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