Boot season is upon us, fashionistas!
Knee high boots are the perfect way to stay warm while still looking incredibly chic.
They effortlessly elongate your legs, add drama to any outfit, and come in so many gorgeous styles.
This fall, knee high boots are having a major moment.
Runways were filled with OTK styles in rich suedes and eye-catching prints.
Street style stars are rocking boots with everything from flowy dresses to skinny jeans.
Knee High Boots with Dresses
My absolute favorite way to style knee high boots is with a dress.
This look is so effortlessly chic and polished.
For daytime, try pairing your boots with a fit and flare dress or an A-line mini.
Look for dresses made of thick fabrics like tweed or textured knits that will keep you warm.
Tights are optional!
For evenings, go for a slinkier, more glamorous silhouette like a bodycon midi or a wrap dress.
Feminine details like ruffles, pleats and lace pair beautifully with boots.
When picking knee high boots to wear with dresses, go for a sleek, simple style that hits below or at the knee.
Neutral colored leather or suede boots are perfect for both day and night.
Stay away from overly embellished boots so the dress remains the focal point.
A classic pair of black riding boots works with any dress style.
For more visual interest, try a printed dress with solid colored boots.
This look is understated yet make a stylish impact.
Accessorizing is easy with this chic combo.
Add a crossbody bag, floppy hat and statement necklace for daytime flair.
At night, carry a minaudière, add a cuff bracelet and style your hair in glamorous waves.
Finish the outfit with simple stud earrings and a swipe of bold lipstick.
Knee high boots plus a dress creates a look that’s elegant, timeless and oh-so enviable!
Boots with Mini Skirt/Short
Mini skirts and knee high boots are a match made in heaven!
This fun, flirty combo is perfect for weekends and nights out.
Choose a skirt that hits a few inches above the knee to show a peek of skin.
Go for bold colors, fun prints or iridescent fabrics to really make a statement.
Pair your mini with a tucked-in sleeveless bodysuit or blouse for a streamlined silhouette.
When it comes to footwear, the posher the better!
Over-the-knee boots add even more visual interest to a mini skirt.
Look for options with block heels, buckles or metallics to complement the short hemline.
If you want to elongate your legs, a pointy toe style is stunning.
For a retro vibe, try a low stacked heel.
Options with slouchy shafts work too for a more relaxed, casual look.
Have fun accessorizing this daring duo!
Statement earrings, piles of bangles and sheer tights all work beautifully.
For evening, carry a tiny clutch and style hair in lush waves.
The pairing of a mini skirt with OTK boots creates a showstopping look that’s daring and bold.
Strut your stuff in this chic combination!
With Skinny Jeans and Blazers
My next fall favorite is knee high boots styled with skinny jeans and blazers.
This polished combo effortlessly takes you from work to weekend.
Dark wash skinny jeans in indigo, black or gray work best and will create a streamlined silhouette.
Look for a stretchy denim that holds you in but is still comfy.
Pair with a tailored blazer in a rich fall tone like emerald, burgundy or navy.
Structured fabrics like tweed, ponte or light wool help balance the casualness of denim.
Look for details like gold buttons, angled hems and shoulder pads to add interest.
Keep the rest of your look simple with a classic button-down or silk cami.
For boots, stick with leather or suede in black, brown or tan.
Almond toe styles are the most versatile and elongate your legs nicely.
Get heels between 2-3 inches for comfortable height.
A block or stacked heel will be sturdy and walkable.
If you want to break up all the neutral tones, look for booties with subtle metallic sheens.
Complete this work-to-weekend look with a ladylike satchel or top-handle bag.
Add a skinny belt at your natural waist to create flattering shape.
Swap out your blazer for a cool leather moto jacket on the weekends.
This edgy yet polished pairing of boots, skinny jeans and blazers works beautifully year-round!
With Faux Leather Leggings
Faux leather leggings are a wardrobe staple and pair so slickly with knee high boots.
Look for leggings in a matte faux leather rather than anything too shiny.
Black is the most versatile and slimming, but rich burgundy and forest green options work for fall too.
Wear with booties that complement or match your leggings’ hue.
When styling, balance the edginess of faux leather with soft, feminine silhouettes on top.
Billowy blouses, cozy knits and flowy tunics help provide contrast.
Leave tops untucked and sleeves rolled for nonchalance.
If you want to nip in your waist, add a skinny belt or fitted jacket.
For footwear, over-the-knee boots look amazing and elongate legs for days.
Pointy toe or almond toe pairs are so flattering.
Go for a mid-height block heel for comfort and walkability.
Metallic, patent leather and textural materials like suede and snake-embossed work well.
Ground the sexiness of your leather leggings with casual pieces like beanies and circle scarves.
Carry a hobo bag or crossbody purse.
Luxe leather boots plus faux leather leggings create a look that’s equal parts edgy and elegant for any occasion.
With Pencil Skirts and Turtlenecks
Few things feel more put-together than knee high boots paired with pencil skirts and turtlenecks.
This chic combination is perfect for work and makes even the dreariest fall days feel polished.
Look for a well-fitting knee length pencil skirt.
Neutrals like black, gray and navy are perfect, but don’t be afraid to make a statement in bold crimson or emerald hues.
Pair your skirt with an autumnal-hued turtleneck.
Cream, brown and oxblood all complement most skirt colors nicely.
Look for snugly-fitting lightweight knits that keep you warm without bulk.
Tuck your top in neatly to highlight your waist and elongate your silhouette.
Then, finish the look with boots that align with the formality of your outfits.
Low block heel knee high boots in leather work well for the office.
For a Friday night date, try a statement kitten heel pair in a fun snakeskin print.
Pointy toe styles look best with pencil skirts.
Dot your I’s with ladylike extras like pearl studs, a quilted crossbody bag and trench coat.
This timelessly chic trio of boots, pencil skirts and turtlenecks makes getting ready a breeze all season long.
Polish has never been so easy!
With Wrap Coats and Trench Coats
Any stylish girl knows knee high boots pair perfectly with tailored outerwear like wrap coats and trench coats.
These posh toppers elongate already-lengthy boots and add refinement to any look.
For a wrap coat, look for options in rich solids like wine, navy and charcoal.
The silhouette naturally cinches your waist, so no need for a belt.
Shawl collar styles look most luxurious.
Complementary textures like herringbone, tweed and wool add visual interest.
Trench coats work well with boots too.
Look for water-resistant cotton or even leather and suede for a unique twist.
Traditional tan and army green hues feel so fall.
Go longer for a dramatic, sweeping silhouette.
Pair these polished toppers with any heel height boot in brown, black or gray suede or leather.
Almond or rounded toe shapes look most flattering.
Leave coat unbelted to highlight the streamlined shape of boots.
Carry a structured satchel bag and don leather gloves for an ultra-polished touch.
Wrap coats and trench coats instantly elevate basic knee highs into a look worthy of street style stardom!
With Feminine Blouses and Midi Skirts
Looking to infuse your fall style with a dose of feminine flair?
Try pairing your knee high boots with delicate blouses and midi skirts.
Look for silky midi skirts in pretty prints and autumnal colors like mustard and ruby.
Billowy A-line shapes fit and flare beautifully when paired with boots.
Pair your skirt with an airy button-down blouse.
Romantic details like ruffles, bows and puffed sleeves add sweet contrast to long-legged boots.
Choose boots with a block or mid-height slim heel to complement the floaty silhouette.
Pointy toe pairs elongate your shape.
Rich suede or velvety leather fabrics work nicely.
Shades of tan, brown, mahogany and black are super versatile.
Finish the look with elegant extras like a felt fedora, circle scarf and ladylike handbag.
The blend of boyish boots with ultra-feminine blouses and skirts creates a lovely balanced look that’s date night perfection!
With Printed Maxi Dresses
Printed maxi dresses get a dose of cool-girl edge when styled with knee high boots.
Look for long-sleeved, fluid jersey maxis covered in whimsical motifs.
Abstract florals, boho paisleys and eclectic geometrics all work beautifully.
Keep the color scheme autumnal with shades of mustard, ruby, olive and russet orange.
Pair your dress with boots in contrasting textures like leather or suede.
Rich brown and black boot colors allow the print to take center stage.
Almond or pointed toe silhouettes elongate and streamline beautifully.
Stay under 3 inches for heels so you remain comfy.
For chillier days, finish with a moto jacket or blanket scarf.
Wide-brim fedoras, crossbody bags and stacks of metal bangles make fun finishing touches.
The juxtaposition of ultra-femme maxis with rugged boots creates a casually chic vibe perfect for fall.
With Cape Coats and Turtlenecks
Make a seriously stylish statement by pairing knee high boots with dramatic capes and turtlenecks this fall.
Look for sweepingly long wool, tweed or cashmere capes in rich hues like wine, emerald and navy.
Oversize shapes look modern and billow beautifully when layered over boot shafts.
Ground the whimsical capes with slim-fitting turtlenecks that neatly tuck into your boots.
Cream, black and gray are perfect neutral shades.
For pops of color, try oxblood, mustard or cobalt knits.
Then finish with almond or pointed toe knee high boots.
Low block heels are comfortable and elegant.
Stick to classic black, brown or tan leather or suede.
Minimal accessories like a leather clutch, skinny belt and oversize sunnies keep the look timeless
Feel like a true style icon in this fashion-forward pairing of capes, turtlenecks and boots.
So dramatic yet refined!
With Bodycon Midi Skirts
Va-va-voom!
For jaw-dropping evening style, try pairing an ultra-fitted bodycon midi skirt with sky-high OTK boots.
Look for skirts that hit right below or at the knee in luxe materials like faux leather, ponte knit or velvet.
Deep greens, shimmering metallics, crimson red and black are gorgeous options.
Pair your slick skirt with an equally head-turning pair of over-the-knee boots.
Look for stiletto or skinny kitten heels for the most leg-lengthening effect.
Pointy toe shapes are super flattering.
Rich suedes, buttery leathers and lacquered patent finishes all work beautifully.
Match your boots to your skirt color or tone for visual impact.
Keep the rest of your look sleek and simple—this bold duo needs no embellishment!
Finish with a silk cami, leather moto jacket and tiny crystal-embellished clutch.
Sculpt bombshell waves in your hair and swipe on a red lipstick.
This daring pairing brings major heat to any evening out!
With Equestrian-Inspired Pieces
Channel your inner equestrian vixen by pairing knee-high riding boots with tailored pieces inspired by polo gear.
Start with sleek high-waisted trousers in autumnal colors like olive green, navy and charcoal gray.
Look for wide leg silhouettes with front seams and pocket details.
Pair with a crisp collared shirt or fitted turtleneck.
Then reach for your most polished pair of riding boots.
Low block heels and sleek, knee-grazing shafts look most elegant.
Stick to dark neutrals like chocolate brown, black and cordovan.
Minimal hardware and almond toe silhouettes keep the look refined.
Add a structured top-handle satchel in a rich tan leather.
Look for extras like an envelope clutch, silk scarf and brimmed wool fedora.
The equestrian-inspired combination of riding boots, tailored separates and posh accessories brings both polish and novelty to your fall looks.
With Tights and Short Dresses
My final fall boot look idea is perfect for showing off your stems even when temps drop.
Pair eye-catching printed tights with short dresses and knee high boots.
Look for short-sleeved, figure-hugging dresses that hit above the knee.
Wrap dresses, fit-and-flare minis and shirtdresses all work beautifully.
Pair with opaque tights covered in whimsical motifs.
Floral prints, geometric patterns and polka dot tights make legs the focal point.
Ground the playful pieces with versatile knee high boots in leather or suede.
Neutral tan, brown, gray and black work with printed tights of all colors and patterns.
Pointy toes lend polish.
Low kitten heels or flats keep you comfy.
Finish with a cropped moto jacket, beanie and crossbody bag for downtown edge.
This upbeat pairing of printed tights, short dresses and boots showcases your fun, flirty style.
The Possibilities are Endless!
Boots instantly pull any outfit together and make getting dressed feel easy and fun.
Follow these ideas to take your fall fashion to the next level.
