MomSkoop
Oversized sweaters are the ultimate cozy wardrobe staple, perfect for chilly days and effortless style.
But finding the right shoes to complete the look can make all the difference between feeling frumpy and looking fabulous.
The right footwear balances out the relaxed vibe of your sweater while keeping your outfit polished and put-together.
Whether you prefer boots, sneakers, or flats, these classic shoe styles will help you nail that perfect cozy-chic aesthetic every single time.
1. Knee-High Leather Boots
Nothing says fall fashion quite like a pair of sleek knee-high leather boots paired with your favorite chunky knit.
The tall silhouette creates a flattering vertical line that balances the volume on top, making you look both comfortable and incredibly stylish.
Black or brown leather works beautifully, giving you options for different color palettes.
The structured material adds polish to an otherwise casual outfit, so you can wear this combo to brunch, shopping trips, or even casual office days.
Pair them with leggings, skinny jeans, or even a mini skirt peeking out from under your sweater for endless styling possibilities.
2. Chelsea Boots
With their sleek elastic side panels and ankle-hugging fit, Chelsea boots bring a touch of British sophistication to your cozy sweater game.
Originally designed for horseback riding in Victorian England, these boots have evolved into a fashion staple that works for everyone.
The streamlined design prevents your outfit from looking too bulky, which is exactly what you need when wearing oversized knitwear.
They slip on easily, making them perfect for busy mornings when you want to look good without much effort.
Choose suede for a softer look or go with polished leather for something more refined and versatile.
3. Ankle Booties
Ankle booties are the Swiss Army knife of footwear—they go with absolutely everything and never let you down.
The shorter height makes them less committal than taller boots, but they still add structure and style to your oversized sweater outfits.
A small heel gives you a little lift without sacrificing comfort, while flat versions keep things super casual and walkable.
The variety of styles means you can choose pointed toes for elegance, rounded toes for comfort, or even cutout details for added personality.
These work wonderfully with cropped jeans, full-length pants, or even dresses layered under your cozy knit.
4. Loafers
Channel your inner preppy fashionista with a pair of classic loafers that add instant sophistication to your sweater look.
These slip-on wonders have been beloved since the 1930s, and their timeless appeal shows no signs of fading anytime soon.
The menswear-inspired style creates an interesting contrast with the soft, feminine vibe of an oversized knit.
Loafers work especially well when you want to look polished but not overly dressed up—think weekend errands, casual Fridays, or lunch dates.
Try them with rolled-up jeans and visible socks for a playful touch, or go sockless for a more streamlined appearance.
5. Ballet Flats
Ballet flats bring an effortlessly feminine touch that softens the bulkiness of oversized sweaters without losing any style points.
Inspired by actual ballet slippers, these delicate shoes became a fashion phenomenon thanks to Audrey Hepburn and have remained popular ever since.
The low profile keeps your look grounded and relaxed, perfect for days when you want maximum comfort with minimal fuss.
They elongate your legs when worn with cropped pants or jeans, creating a clean line from hem to toe.
Choose classic black for versatility, nude shades to lengthen your legs, or fun prints and colors to add personality to neutral sweaters.
6. Mary Jane Flats
Remember those adorable shoes from childhood?
Mary Janes have grown up and become a surprisingly chic option for pairing with your favorite oversized knits.
The signature strap across the instep adds a playful vintage charm that feels both nostalgic and fashion-forward.
This style works particularly well when you want to add a touch of whimsy to your outfit without going overboard.
The secure strap also means they stay put better than regular flats, making them practical for longer wear.
Style them with tights and a sweater dress, or keep it casual with jeans—either way, you get that perfect mix of sweet and sophisticated.
7. Combat Boots
Want to add some edge to your cozy sweater collection?
Combat boots are your answer, bringing tough-girl attitude that perfectly contrasts with soft, fluffy knitwear.
Originally military footwear, these boots have been adopted by fashion rebels and style enthusiasts alike since the punk movement.
The chunky soles and heavy-duty laces create visual weight at the bottom of your outfit, balancing out the volume on top.
They make even the girliest oversized sweater look a little more badass and a lot more interesting.
Wear them with distressed jeans for a grunge vibe, or pair them with a flowy skirt for that unexpected mix that fashion editors love.
8. Western Boots
Yeehaw! Western boots bring a dose of country charm and unexpected personality to your oversized sweater wardrobe.
The distinctive pointed toes and decorative stitching make these boots true statement pieces that turn heads wherever you go.
What makes them work so well with chunky knits is the way they add structure and interest to the bottom half of your outfit.
The slight heel gives you height without the discomfort of traditional heels, and the shaft height can vary from short to tall depending on your preference.
Style them with tucked-in jeans to show off the boot details, or let them peek out from under wide-leg pants for a modern twist.
9. Slouch Boots
For maximum coziness from head to toe, slouch boots are the perfect companion to your oversized sweater collection.
The relaxed, gathered shaft creates soft folds around your calves, echoing the comfortable, lived-in feel of your favorite knits.
These boots became wildly popular in the 1980s and have made several comebacks since, proving their enduring appeal.
The unstructured design means they mold to your legs over time, becoming more comfortable with each wear.
They look amazing with leggings, skinny jeans, or even tucked-in boyfriend jeans for a casual weekend vibe.
Suede versions feel especially luxurious and pair beautifully with neutral-toned sweaters.
10. White Sneakers
Clean, crisp white sneakers have become the unofficial uniform of effortless cool, and they look absolutely perfect with oversized sweaters.
The fresh, sporty vibe keeps your cozy knit from feeling too dressy or formal, striking that ideal balance between comfort and style.
Whether you choose classic canvas or premium leather, white sneakers brighten up your entire outfit and make even the chunkiest sweater look intentional and put-together.
They work for running errands, meeting friends, or basically any casual occasion you can think of.
Keep them relatively clean for maximum impact—scuffed sneakers lose some of that crisp, polished appeal that makes this combination work so well.
11. Retro Running Sneakers
Chunky retro running sneakers bring a fun, nostalgic energy that turns your oversized sweater into a full-on athleisure statement.
These throwback styles from the 80s and 90s have roared back into fashion, with their bold colors and exaggerated proportions fitting perfectly into modern streetwear aesthetics.
The substantial sole and eye-catching designs add personality to simple sweater outfits that might otherwise feel too plain.
They work especially well with neutral-colored knits, where the sneakers become the focal point of your look.
Style them with high-waisted jeans, joggers, or even bike shorts under your sweater for that trendy, sporty-chic vibe that dominates social media feeds.
12. Heeled Sock Boots
Sleek and modern, heeled sock boots create a streamlined silhouette that elevates your oversized sweater from casual to sophisticated in seconds.
The stretchy, glove-like fit hugs your ankle and calf, creating a seamless line that elongates your legs beautifully.
These boots became a runway favorite in recent years and quickly trickled down to everyday fashion for good reason—they look expensive and fashion-forward without trying too hard.
The heel adds height and elegance, making them perfect for date nights or dressier occasions.
Pair them with a sweater dress for a chic monochromatic look, or wear them with skinny jeans tucked in to show off their sleek design.
13. Classic Pumps
Who says oversized sweaters can’t be office-appropriate?
Classic pumps instantly polish up your cozy knit, transforming it from weekend loungewear into workplace-ready attire.
The refined silhouette and elevated heel bring sophistication that balances the casual nature of chunky sweaters.
Pointed toes elongate your legs and create a sleek line, especially when worn with tailored pants or a pencil skirt.
Nude pumps are particularly magical because they blend with your skin tone, making your legs appear even longer.
This combination proves you don’t have to sacrifice comfort for professionalism—just tuck your sweater into high-waisted trousers, add pumps, and you’re ready for meetings.
14. Suede Chukka Boots
Suede chukka boots bring a refined casual vibe that works beautifully for both men and women styling oversized sweaters.
These ankle-high boots with their minimalist two or three-eyelet lacing originated as desert boots worn by British soldiers, but they’ve evolved into a versatile style staple.
The soft suede texture complements the cozy feel of chunky knits while maintaining a put-together appearance.
They’re dressy enough for casual Fridays at work but comfortable enough for weekend adventures.
The neutral tones of most chukkas—think sand, taupe, or chocolate brown—coordinate effortlessly with virtually any sweater color in your closet, making them an incredibly practical investment piece.