The Best Fall Outfits with Knee-High Boots You Need to Try
Photo:@jariatudanita
Knee-high boots are the wardrobe staple we’re all obsessed with—especially as the colder months approach. Whether you’re rocking skinny jeans, a mini skirt, or even a sweater dress, there’s just something about knee-high boots that instantly elevates any look. From block heel to flat knee-high boots, they offer the perfect blend of comfort, style, and warmth for the winter months.
What makes knee-high boots so iconic? Well, they’re not just for show—this type of footwear is both functional and versatile. Whether you're slipping into leather boots or cozying up in a suede pair, these boots work across a range of outfit ideas and always deliver a stylish look. Need to take your pencil skirt from the office to a date night? Or maybe you’re pairing tall boots with a denim midi skirt for that perfect street style vibe. Either way, knee-high boots are the go-to for fall and winter.
With so many styles—think heeled, flat, slouchy, or western-inspired boots—there’s a great choice for everyone. You can choose different colors to match your vibe, from classic black knee-high boots to bold brown boots. And let’s not forget the suede boots with a pointy toe or stiletto boots for a night out, or the flat boots and riding boots for those everyday looks. Extra points if you pair them with a statement coat or a chunky knit for that ultimate cozy but chic fit.
No matter how you style them, knee-high boots are the hero piece your fall and winter wardrobe needs. Stay tuned for new ways to rock these classic pieces—trust us, your winter season is about to get a whole lot more fashionable.
Knee-High Boots with Dresses
Photo:@yhasmina.ferrara
One of the easiest (and cutest) ways to style knee-high boots is with dresses. Whether you're going for a cozy sweater dress, a flirty mini dress, or a flowy midi length option, knee-high boots add instant polish to your look.
For fall, try pairing flat knee-high boots with a chunky sweater dress—it’s the ultimate comfy yet chic combo for those chilly winter months. The key is to keep the outfit balanced: if you’re wearing a short skirt or mini dress, opt for knee-high boots to elongate your legs and add a bit of warmth (bonus points if you throw on some sheer tights). The contrast between bare legs or tights and tall boots always gives that cool, off-duty model vibe.
If you’re a fan of longer styles, midi dresses or shirt dresses work beautifully with heeled knee-high boots. A fit-and-flare or A-line dress paired with tall boots creates a flattering silhouette, perfect for transitioning from day to night. Add a long coat or trench coat for a layered fall look, and you’re all set for everything from a brunch date to an evening out.
Same Edelman
Sylvia Knee High Boot
$200.00
Knee-High Boots with Skirts
Photo:@peexo
Styling knee-high boots with skirts is an easy way to elevate your outfit while keeping things chic and cozy for the colder months.
Let’s start with mini skirts—pairing a leather mini skirt with knee-high boots is the ultimate edgy look for fall. Add a chunky knit sweater for balance, and you’ve got the perfect combination of cozy and cool. The contrast between the short hemline and tall boots elongates your legs and gives off serious street style vibes.
For a more classic look, try a pleated skirt or a midi length skirt with heeled knee-high boots. The longer skirt paired with heeled boots keeps your proportions in check, giving you a flattering silhouette. Plus, the added height from the heels creates a more polished look that can take you from day to night. Whether it's a pleated midi skirt or a flowy long skirt, adding knee-high boots keeps the look modern and chic.
If you're looking for a balance between casual and put-together, pair knee-high boots with a pencil skirt. It's a versatile look for both work and weekend outings. Add a fitted turtleneck or a long coat for a sophisticated outfit that works for the winter season while still being comfortable and stylish.
Stuart Weitzman
Yuliana 85 Slouch Boot
$895
Knee-High Boots with Leggings
Photo:@gabriellamichin
Let’s be real—pairing knee-high boots with leggings is one of the easiest ways to look stylish without sacrificing comfort. Whether you’re running errands or heading out for the day, this combo is all about looking sleek and feeling good.
Throw on a pair of leather leggings with some knee-high boots, and you’ve instantly got an edgy, modern vibe. Want to add some layers? Go for an oversized shirt, a cool leather jacket, or even a blazer for a more polished feel. For those cozy days, a chunky oversized sweater or a chic trench coat will keep you warm and stylish.
The best part? Leggings are versatile enough for any mood. If you’re keeping it casual, try flat knee-high boots with your go-to black leggings and an oversized sweater. Want to dress it up a little? Rock some heeled knee-high boots with your leather leggings and a sleek long coat or tailored blazer—you’re instantly ready for anything.
Lulus
Katari Off White Pointed-Toe Knee High Boots
$49
Knee-High Boots for Workwear
Photo:@missy_elz
Who says you can’t bring your favorite knee-high boots into the office? With the right styling, they can totally work for a professional yet stylish look. The key is pairing them with polished pieces that balance the boldness of the boots while keeping it office-appropriate.
For a sleek, no-fail combo, pair your knee-high boots with a classic pencil skirt. The fitted skirt balances the tall boots, giving you that perfect blend of chic and professional. Add a structured blazer or a tailored trench coat, and you’re ready to command any meeting with confidence.
Bonus: this look transitions easily from workday to date night.
If skirts aren’t your thing, knee-high boots also look amazing with tailored dresses. Opt for a midi-length dress to keep the look polished and professional—whether it’s a shirt dress or a more fitted style. Throw on a long coat or blazer to complete the ensemble.
Need something versatile for those long office days? Try knee-high boots with a long denim skirt or a more structured leather skirt. Top it off with a sweater vest or moto jacket to give it an edge while staying work-appropriate.
With the right combinations, knee-high boots can be a stylish addition to your work wardrobe, making you feel fashionable without breaking the office dress code.
Sam Edelman
Sylvia Wide Calf Knee High Boot
$250.00
