10 Shoes I’d Wear with Sweater Dresses (and a Few I’d pass on)

Sweater dresses are my favorite go-to in winter. They’re classy, cozy, comfy, and perfect for my casual lifestyle. They’re also very versatile.

Since sweater dresses are pretty plain to start, there are many ways to style them. You can layer and accessorize them, adding your own personal flair. Within minutes, you’ll have a whole new outfit! 

Shop these shoes at my LTK shop.

Of all the ways you can tweak a sweater dress to make it more interesting, changing up your shoes makes the biggest difference. There’s no real secret to this. Basically, every style of shoe works, but some look so much better than others.

Today, I’m sharing a round-up of the 10 shoes I’d wear with a sweater dress and a few more you want to try, too.

10 Shoes To Wear With Sweater Dresses

V neck Sweaterdress with Suede Booties

1. Ankle Boots 

Ankle boots worn with short and midi-length sweater dresses are a modern pairing. But to look chic, your ankle boots should be short enough to show more than just a sliver of skin between your dress and boot.  It also looks better if your boots are narrow at the ankle and shaft.

Tip: Show more than just a sliver of the leg between the hem of the sweater dress and the top of the bootie. This is a decent amount.

Ankle boots that end too close to your dress hem and are too wide around your legs will make your legs look chunky and heavy. This is true whether you wear bare legs or tights with your ankle boots. If you prefer wearing tights, as I usually do, that’s fine, but your tights should be the same color as your boots so the proportions look right.

Match your stockings to your boots for longer legs

Do your boots need to be a similar color to your dress, or should they contrast? That’s a personal choice. I find the same color or tone-on-tone is more elegant and elongating, but contrasting colors can also look chic.

The best thing about ankle boots is that there are so many styles to choose from. There are fine, low-heeled Chelsea ankle boots and sleek, pointy-toe high-heeled booties. For a dressier look, I like sexy sock booties with a ladylike heel, but chunky heel ankle boots can look great, too. If you want a boot with a touch of embellishment, these glam rhinestone booties are fun but don’t overpower.

Nothing beats tall, sexy boots with a sweater dress

2. Tall Knee High Boots

Knee-high are my favorite boots to wear with a sweater dress. They make you look elegant, feel confident, and send out those boss babe vibes! You can wear knee-high boots with an above-the-knee sweater dress with some skin showing or tuck them up under a midi sweater dress.

It’s flattering when your midi sweater dress had a has a sexy slit at the side, or front to show off the boot. If you have a button-up sweater dress, you may even want to unbutton the last few buttons to show off your boots. 

You want to avoid having your knee-high boots awkwardly meet at the hem of your sweater dress, rubbing against it, and catching on your shoes when you take a step.  

Suede goes well with a sweaterdress because of the texture and weight.

I usually  go for knee-high boots with a pointy toe because they make my legs extra long, but some women prefer a more almond shaped toe.  This year, a slightly squared-off toe is trending, and I think it works, too. Check out these gorgeous Knee-high boots with chunky block heels are not as dressy as a fine heel, but what I like about these Sam Edelman ones is that from the side, they look fine, but from the back, they are wide and sturdy—the best of both worlds.

If you are wondering about leather versus suede, leather knee-high boots are a little more formal than soft suede ones. However, I prefer suede. I find suede casually elegant and more in sync with the weight and texture of a cozy knit.  

Mary Jane Ballet Flat feel comfy, look modern – Sweaterdress | Mary Janes

3. Ballet Flats/Mary Janes

At one time, I would have said no to ballet flats with sweater dresses. I was a heels girl and these seemed kind of frumpy. But since I’m now more into flats in general, and all these cute Mary Jane flats (and low heels) are in style, I’m changing my mind.  Ballet flats are a comfy, sophisticated option.  I’ve seen many women over 40  embrace the ballet flat comeback.

These Greta ballet flats with a strap have been a big hit and look kind of cute with a sweater dress outfit. If you are real shoeaholic and you don’t mind spending more, I adore these black pointy ballet flats Mary Janes!!

Sneakers are cool with this Polo Sweater Dress

4. Sneakers

Here’s another unexpected kind of shoe I think looks great with sweaterdresses. Cute lace-up sneakers like trendy Sambas or slip-on sneakers give a timeless sweater dress a spunky modern twist. I see a lot of gals wearing them, especially with loose-fitting sweater dresses that are a little more on the chunky side. I also notice they’re a natural with sporty, striped sweater dresses. 

The only word of caution is that I would avoid wearing sneakers with thin, fine-knit sweater dresses, bodycon, or fit-and-flare styles. These just don’t have the right look for sneakers. Other than that, sneakers with your sweater dresses are a great way to add a sporty edge and look youthful.

5. Heeled Pumps

You can’t get more classic than a heeled pump (thin or block) with a sweater dress. Pumps are a go-to shoe when you don’t want to wear boots because they always look classy. A pointy toe is more elegant than a round or square toe and helps elongate your legs.

If your pumps are plain—let’s face it—they can make your outfit look a bit boring. So, I suggest you get on the slingback train and get yourself a pair of elegant slingback pumps. I adore slingback pumps and slingback flats, and I think you will be shocked by how this small tweak can totally modernize your look.

These black strappy sandals look classic with this Fit and Flare fine knit sweater dress.

6. Strappy Sandals

This one depends because sometimes strappy sandals can look a bit off with sweater dresses. I live in a four-season climate, so they seem far too unseasonal to wear with a sweater dress that you’d wear mostly in fall or winter.

If you live in a warm climate, then strappy sandals with a sweater dress makes more sense. I’ve seen them work with a fine, lightweight sweater dress. But there’s a real disconnect you try and pair strappy high-heel sandals with a  thick heavier, chunky sweater dress ( ie: heavy ribbing, cableknit). The sweaterdress outfit looks fine with a thin, strappy, open-toe sandal.

Another option in place of a strappy sandal could be a closed toe strappy slingback. This would be my choice.

      Ruched Boots with a Sweater dress

7. Slouchy Boots

Slouchy boots with soft folds are a cool way to add texture and an ethnic boho vibe to a sweater dress. They’re not tall enough to go over your knee, but they’re not short enough to be considered an “ankle boot,” either, so you either have to wear them under a midi or have enough space between your hem and the boot to show some leg.

Nine West has the most flattering pair of slouchy boots, ready to be paired with any oversized sweater dress look! I also like these budget-friendly slouchy boots from The Drop at Amazon.

The latest Western Boots –  sweaterdress

8. Western Boots

Yee Haw, I didn’t see this one coming! I’ve always thought Western Boots looked a little costume-like, but the latest ones that are trending are much more sleek, refined, and feminine. (You can see a pattern here in the types of shoes and boots that I like.) Short Western boots and tall Western boots can work really well with the relaxed look and feel of a sweater dress, especially a chunky one.

The new trend in mules – mules with Mary Jane type straps – Sweaterdress

9. Heeled Mules/Flat Mules 

Heeled mules with a sweater dress can look casually chic. I love these Ann Taylor suede mule pumps with the chain detail to wear with a classy dress or these Lorelei mules with a comfier, blockier heel that can be better for longer wear. 

If you like to slip your shoes on and off but don’t like heels, you can opt for flat mules. These are a mix between a sophisticated loafer and a comfy ballet flat (heeled ones here). The only thing with mules is they are not the most practical. They can look kind of cool, but not if they are always falling off your feet!

Sweaterdress with loafers

10. Loafers

This can sometimes feel like a funny pairing at first but some loafers can look quite chic. I say “some: because although you see a lot of chunky platform loafers on line,  I prefer the the sleeker more elegant ones. The trendy heavy-sole loafers are too clunky and masculine for my style.

However, if you want a tailored vibe, a loafer with a flat or low heel, like these elegant  Quince Italian suede or  leather loafers, can look very sophisticated. They’re a modern version of the old money look. These subtle snake print loafers are also nice.

Shoes I’d pass on when Wearing a Sweater Dress. (There is no right or wrong here. This is just me!)

Combat Boots

I never wore combat boots in the 1990s, and I’m not going to start now. Combat boots with a sweater dress are too edgy a pairing for me. However, if you have ever asked yourself, “How can I wear combat boots after 40, 50, or 60+ and not look like a “granny,” this is a popular look, for sure.

Lug Sole Chelsea Boots

Lug Sole Chelsea boots are similar to combat boots; They are chunky, round toed, practical, but less military. They’re stylish to wear with a sweater dress  (chunky or oversized), but again, this isn’t my vibe. 

If this feels closer to your style, these Cole Haan booties are kind of fun, and you’ll forget that they’re designed specifically for the winter.  You can grab them in leopard print to elevate a black sweater dress or buy black for a safe bet that they’ll go with just about everything.

Oxfords

Oxfords or brogues have a preppy vibe and you might well love the look, but it feels too school librarian to me. Not exciting.

Over the Knee Boots

Over-the-knee boots with short sweater dresses are fashion-forward and in some instances I kind of like the look, but generally they feel more like a younger, creative look to me. The cool way to wear these boots is underneath a loose, chunky, belted sweater dress with no leg showing; otherwise, it’s too pretty woman. Think of over-the-knee boots like extra-thick leggings that you would pair with a sweater dress.

Riding Boots

Classic Low-Heeled Riding Boots always look classy with sweater dresses, even though they have been a little more on the back burner the last couple of years. If you like a traditional look, riding boots and a sweater dress are a timeless combo.

How To Accessorize A Sweater Dress To Match Your Shoes

Once you have decided on your shoes for your sweater dress, just add accessories to tie the whole look together and make it your own.

Love when the belt matches the boots! Dress | Boots

Could you add a statement belt for definition?

Sweater dresses can be baggy and make you look boxy. You can use a chic statement belt to define your waist. Choosing the right belt is like selecting the right handbag for your body type.  It’s all about finding the right belt that suits your unique shape. For example, long-waisted women can get away with a wider belt, while short-waisted women need a thinner belt. 

Incorporate jewelry to create a focal point.  

Layer a few necklaces on a crew or round-neck sweater dress to liven it up. Wear a longer necklace on a high-neck sweater dress to draw the eye down and create balance. Vneck? Could you fill in the space with a pretty pendant?

Play with scarves, coats, or cardigans for a textured look

A sweater dress is soft and rounded, so it looks great when layered with a structured piece like a trench coat, blazer, cardigan, or lightweight printed scarf. Match the color of your layer to your shoes for a more coordinated look.

Could you finish your look off with your favorite bag? 

A beautiful handbag polishes your look and brings it all together, including your shoe choice. A soft bag works well with a more casual look, and a structured bag is more appropriate for a more serious or dressy look.

Red sweater dress with same color shoes is monochromatic which is very classy.

What shoes are you planning to pair with your sweater dress outfits this winter?

It’s easy to go into the winter season and think that you’ll be stuck with the same dresses and boots that you’ve rotated in your wardrobe for years. That’s not the case this year, gals! You can look age-amazing by switching up your style and expanding your shoe closet.

Yes, it’s scary to step outside of your comfort zone. But life is too short not to feel like the best, most fashionable version of ourselves. I hope some of you got some fun and stylish inspo from these outfit ideas. Let me know in the comments how you’re wearing your sweater dresses this season!

Please visit my LTK storefront so you can see all of my favorite pieces in one place.

Don’t forget to show and tell me about your favorite shoes to pair with sweater dresses when you visit The Fabulous After 40 Dressing Room, which you’re able to join right here!