Fall is upon us which means it’s time to transition our wardrobes for the cooler weather.
This season, I’m loving ankle boots with jeans!
Ankle boots are the perfect partner for jeans, whether you prefer a skinny jean or mom jean.
They allow you to show off your leg without sacrificing warmth.
Ranging from edgy biker boot looks to classic riding boots, you’ll find inspiration here for any event or occasion.
Some key ankle boot styles I’ll be highlighting include chunky Chelsea boots, western-inspired pull-on boots, and sleek knee-high combat boots.
Denim & Boots Style : Photo Gallery
Black Chelsea boots with skinny black jeans
Black Chelsea boots with skinny black jeans is a classic combo that never goes out of style. The slimming all-black look is ultra-polished and flattering.
For the perfect fit, opt for skinny black jeans that hug your ankles smoothly down into the boots without bunching. The sleek silhouette should flow seamlessly.
Chelsea boots look especially crisp and clean when kept below the ankle bone. Make sure to try different heel heights to find your most comfortable fit.
Add visual interest with textured or knit tops in colors like burgundy, navy or olive green. Try a ribbed turtleneck, cozy sweater or statement blouse.
Dress it up with a blazer or dress it down with a moto jacket. A longline jacket or cardigan also helps balance the slim-fitting silhouette.
Accessorize with mixed metal chunky jewelry, such as layered necklaces, rings or bracelets. Opt for on-trend gold or silver tones.
Finish the look with a shoulder or crossbody bag in a complementary color and texture like leather or woven rattan.
Most importantly, be confident in this flattering yet effortlessly cool ensemble!
Western booties with ripped light-wash cropped jeans
Western-inspired booties, with details like buckles or fringe, give any outfit a cool Western flair. They work especially well with light-wash jeans.
Ripped jeans add an edgy twist. Look for lightly distressed and faded crops that show some ankle. The rips accentuate the legs.
A cropped length displays the booties and balances out the slouchiness of the jeans. Cuff the jeans once if they’re too long.
This combo has plenty of vintage-inspired charm. Accessorize with woven belts, layered necklaces and broad-brimmed hats for full Western vibes.
Top it off with a lightweight shirt or blouse in a soft solid like white or blush pink. Flowy fabrics add to the effortless feel.
For cooler weather, layer a plaid flannel or denim shirt over the top with the sleeves rolled.
The mixture of textures, from the worn denim to buckled leather to shabby chic details, makes this look delightfully lived-in and cool-girl casual.
Booties and ripped crops are a flirty, youthful match made for country-chic days out exploring local artists, farms or flea markets. Yeehaw!
Knee-high lace-up boots with dark denim cigarette pants
Knee-high lace-up boots with a panel design are striking and sophisticated.
The detail draws attention to your legs in a flattering way.
Pair them with fitted dark denim cigarette pants for a sleek, elongated silhouette. Cigarette pants hug the leg for a leg-lengthening effect.
Opt for a rich indigo or black denim shade to complement black boots. The monochrome look is ultra-polished.
Tuck in a silk blouse or cashmere sweater to showcase the contours of the pants. Opt for neutral tones like white, cream or charcoal grey.
Cigarette pants often have front pleats or creases – take time to sharply press and shape the pleats for a refined appearance.
Finish with tailored outerwear like a blazer or longline coat. Belts or waist bags also help accentuate your figure.
Wear with heels for a head-turning work ensemble or switch to block heels for all-day comfort.
This ensemble flatters all heights with its leg-lengthening details. Have fun adding designer touches like a monogrammed blazer or handbag.
Platform boots with white wide-leg jeans
Platform boots add instant edge and swagger to any outfit.
When paired with billowy white wide-leg jeans, they create a unique statement look.
Look for chunky platform boots in leather or pleather with gripped soles for traction. The extra height emphasizes the flared silhouette of the jeans.
Wide-leg or parachute cut jeans in a crisp white shade are eye-catching and allow the boots to shine. Cuff the hems once to highlight the sole.
Consider styling this look with creatively cut or graphic tees tucked in to show off your platform footwear. Try a color-blocking, tie-dye or cropped design.
Finish with oversized accessories like XXL hoop earrings, chunky rings or layered necklaces for maximum impact.
For cooler weather, top it off with an oversized blazer or denim jacket to balance the voluminous bottom half.
Platform boots + billowy pants can seem unwieldy, so accessorize minimally and allow the statement pieces to stand out.
Opt for a neutral makeup look to let the fashion-forward shoes and jeans do the talking! Be bold and own the playful proportions.
So in summary – let platforms and wide-legs dominate this uber-cool, statement look!
Pointed-toe booties with skinny dark-wash jeans
Pointed-toe booties are a sleek shoe silhouette that works for the office or evenings out. They pair especially well with skinny jeans.
Dark indigo or black skinny jeans complement the low-key elegance of pointed toes. Opt for a heavy stretch fabric for comfort.
Skinnies hug the leg down to meet the booties without bunching for a polished, flawless look.
A crisp button-down shirt or fitted knit top in core shades like white, light blue or blush pink flatters this ensemble.
Accessorize with understated gold or silver jewelry – small stud earrings, a bangle, and your favorite watch.
Carry a structured work tote or classic purse in pebbled leather or suede to match the shoes.
Pointed booties give you a few extra inches of height without compromising mobility, perfect for busy days on your feet.
For cooler nights, throw on a lightweight blazer, blazer, cardigan or moto jacket to complete the look.
This head-turning outfit excels whether you’re in the boardroom or lounge hopping after dark. Simply chic!
Riding boots with straight-leg light-wash jeans
Equestrian-inspired riding boots are an effortlessly cool choice for fall. They pair beautifully with classic straight-leg jeans.
Opt for a lighter medium to light wash denim for straight-legs. The casual style washes like a cool-toned, lived-in jean.
Mid-calf riding boots with a rounded toe and sturdy heel are versatile and flattering. Look for leather or suede in natural shades like brown or black.
Straight-leg jeans hit right at the top of the boot shaft for a polished fit. Try different rises like mid or high to find your favorite silhouette.
Elevate the look with cozy knitwear – chunky turtlenecks, cable knit sweaters or collarless coats frame the outfit perfectly.
Layered necklaces, an arm party of bangles, or a plaited leather belt add equestrian charm.
On blustery days, a plaid scarf or beret completes the countryside-chic vibe.
Riding boots are comfy enough for all-day wear. Jeans are your grounding staple piece. Together they make easy yet engaging outfits for errand running or weekend adventures.
Most of all, embrace your inner horse girl spirit! Trot around showing off your effortless style.
Military-inspired boots with boyfriend jeans
Military-inspired ankle boots with chunky soles and buckle details add an edgy utility touch to any ensemble. They pair particularly well with boyfriend jeans.
Boyfriend jeans have a relaxed, slouchy yet flattering fit.
Opt for a medium or light wash denim without embellishments.
Assemble the look with an oversized layered top in a cozy knit or soft linen. Roll up the sleeves for ease of movement.
For accessories, think dog tags, cross-body bags or watch caps. Finishing touches from the barracks like this complete the military vibe.
Chunky military boots have extra ankle support and traction ideal for unpredictable weather or uneven terrain.
The height provides inches without constricting movement. Boyfriend jeans are comfortable all day.
Together, these pieces make relaxed yet rebellious outfits for hiking trails or downtown exploration.
On cooler days, top with a chore coat, bomber jacket or peacoat in olive, army green or navy for harmonizing utility.
Most of all, exude confidence as you stride around town in this badass uniform that’s function meets fashion! Own the off-duty soldier look.
Oxford lace-up boots with black high-waisted jeans
Oxford lace-up boots have a classic masculine charm that works perfectly with jeans. The smart silhouette pairs especially well with high-waisted styles.
Opt for sleek black jeans that hit right at the natural waist or above for an elevated look. Skinny or straight-leg cuts both work well.
The high rise and oxford lace-ups balance each other out – one is streamlined while the other has characterful detailing.
Tuck in structured blouses tucked in neatly to showcase the proportions. Opt for neutral shades, prints or fabrics like checks.
A fitted blazer in black, gray or navy polished off the outfit neatly for the office or weekend.
Accessorize simply and let the jeans and shoes shine – think small hoops, a watch or statement bag.
Oxford boots provide ankle support and stability for long days on your feet. High-waisted jeans flatter your figure.
On colder days, layer tights or knee-high socks underneath for added warmth without compromising the fit.
With a little coordination, this urban chic combination makes a compelling yet comfortable ensemble for class or client meetings. Very professorial vibes!
Leather ankle boots with rolling hem cropped jeans
Leather ankle boots polish off casual looks in fall and winter. They pair especially nicely with cropped jeans.
Go for high-quality leather ankle boots in black, brown or burgundy with a rounded or almond toe. They should hit right at the ankle bone.
Cropped jeans that hit right above the ankle bone show off the boots beautifully. A thin rolling hem adds polish.
Light to medium washes on the cropped jeans keep the monochrome look cohesive. Skinny or straight-leg silhouettes both work well.
By shortening the jeans, ankle boots become the focal point. Their clean lines elongate the leg.
Layer knitwear like Crop sweaters or bodysuits to balance the proportions. Opt for neutral tones or colors like olive, burgundy or navy.
Add dainty gold or silver jewelry for a pulled-together outfit. Small hoops or layered necklaces are ideal.
Since boots are closed-toe, jeans can be worn year-round. Together they offer effortless style suitable from classroom to happy hour.
Most importantly, flaunt your ankle game! This look accentuates your legs in a subtle yet super flattering way.
Buckled block-heel boots with ripped boyfriend jeans – Edgy rocker girl aesthetic
Buckled block-heel boots add edgy attitude to any outfit. They pair especially well with ripped boyfriend jeans.
Look for boots with thick block heels, multiple buckles, and signature ripped details. Leather or pleather fabrics work well.
Ripped boyfriend jeans in a worn, faded blue add grungy charm. Distressing around the knees is key. Cuff the hems once.
Layered necklaces, spiked cuff bracelets, and on-trend small shoulder bags complement the edge.
Opt for cropped or off-the-shoulder tops in dark neutrals like black, gray or crimson to flatter your figure underneath the looser jeans.
Finish with a faux or real leather jacket for a true rocker babe vibe. Moto styles accentuate the slouchy-meets-sleek proportions.
The heels and rip details create motion and visual interest with each stride. Own your inner bad girl confidence!
Block heels provide lift without compromising comfort for shows, concerts or cruising town.
This style makes weekend festival outfits or night-out looks with an attitude. Let your tough-chic personality shine!
Knee-high faux suede boots with tapered dark-wash jeans
Knee-high boots add luxury and allure to any outfit. Faux suede is a budget-friendly yet still luxe material.
Look for fitted knee-high boots with a rounded or pointed toe. Dark brown or black shades complement a variety of bottoms.
Tapered jeans in a rich dark indigo wash are flattering and refine the look. Skinny jeans can also work.
The fit should be snug through the thighs then taper neatly into the boots without bunching.
Layered knitwear like turtlenecks or cozy sweaters balance the proportions while keeping you cozy as temperatures drop.
Accessorize with delicate gold chains, small hoop earrings and crossbody bags for touch of glitter.
Knee-high boots visually elongate your legs for days. Paired with a flattering jean fit, they create a striking silhouette.
Wear with block or stiletto heels interchangeably. Heels dress the look up while flats keep it comfortable.
On chilly nights, finish with a woven coat, teddy jacket or long cardigan to cuddle up in bogus luxe style.
Embrace your inner goddess vibes as you strut around town in this sleek yet sumptuous ensemble!
Pull-on moto boots with wide-leg jeans
Knee-high boots add luxury and allure to any outfit. Faux suede is a budget-friendly yet still luxe material.
Look for fitted knee-high boots with a rounded or pointed toe. Dark brown or black shades complement a variety of bottoms.
Tapered jeans in a rich dark indigo wash are flattering and refine the look. Skinny jeans can also work.
The fit should be snug through the thighs then taper neatly into the boots without bunching.
Layered knitwear like turtlenecks or cozy sweaters balance the proportions while keeping you cozy as temperatures drop.
Accessorize with delicate gold chains, small hoop earrings and crossbody bags for touch of glitter.
Knee-high boots visually elongate your legs for days. Paired with a flattering jean fit, they create a striking silhouette.
Wear with block or stiletto heels interchangeably. Heels dress the look up while flats keep it comfortable.
On chilly nights, finish with a woven coat, teddy jacket or long cardigan to cuddle up in bogus luxe style.
Embrace your inner goddess vibes as you strut around town in this sleek yet sumptuous ensemble!
Sock boots with skinny gray jeans
Cozy sock boots are a quintessential cold weather shoe. They pair especially well with monochrome skinny jeans.
Look for allover wool or fleece-lined sock boots in gray, black or camel shades to match the jeans seamlessly.
Skinny jeans in a lightweight gray or charcoal fabric cuff neatly into the boots. Opt for ankle or regular lengths.
Let the minimalist monochrome palette take center stage – accessorize simply with beanies, scarves and small crossbody bags.
Oversized knit sweaters or cozy sweatshirts in heathered tones keep the outfit cozy from neck to toe.
On blustery days, add insulating layers like fleece-lined tights under jeans for irresistible warmth.
Sock boot grip and snug ankle bands provide traction on icy paths. Skinnies are flexible for busy days.
Carry a thermal mug for hot drinks on the go in this portable yet plush winter outfit.
Subtly chic and delightfully comfortable – this monochrome combo is perfect for lazy days lounging or running errands around town.
Brogue booties with acid-wash skinny jeans
Brogue booties are a quirky shoe style with vintage flair. Their perforated details pair perfectly with acid-wash jeans.
Look for leather booties in black or brown with an almond toe and low chunky heel. Brogue patterning adds visual interest.
Acid-washed skinny jeans in light blue or powder pink have a broken-in, lived-in look. Opt for styles with subtle fading and whiskering.
These jeans cropped right at the brogue’s ankle strap show them off beautifully. Make sure the fit is super slim through the leg.
Tuck in graphic tees, cropped band tees or babydoll blouses with a ’90s retro flair. Neon tones really make the acid wash pop.
Layered beaded necklaces, baby bangs hairstyle, tinted sunglasses – finish the look with throwback accessories for maximum y2k vibes.
Brogues are dressy enough for downtown weekends yet comfortable for all-day adventures around town.
On cooler nights, top the look with an oversized cardigan, plaid flannel or denim jacket for complete vintage inspo.
With their one-of-a-kind personality, this outfit is sure to spark joy and nostalgia wherever you roam! Now you’re in the zeitgeist, baby.
Combat boots with relaxed tapered jeans
Combat boots add an edgy punk rock vibe to any outfit. They pair especially well with tapered jeans.
Opt for sturdy leather or suede combat boots in black with buckles/laces and sturdy sole. Go for broken-in styles with distressing.
Relaxed tapered jeans in medium or light wash create an intentionally slouchy silhouette without being baggy.
The jeans should taper gently from hip to ankle to flow into the boots. Cuff once for visual interest.
Layer band/graphic tees, plaid shirts unbuttoned or cropped tanks for rebellious weekend looks.
Spiked cuffs, chunky chain necklaces and worn-in leather jackets lend punk stylistic touches.
Combat boots support all-day roaming and standing at shows. Tapered jeans straddle casual-cool.
On chilly evenings, pair with jackets featuring patches, pins or written messages of rebellion.
Exude carefree confidence as you conquer the days and nights in this defiant yet effortless street style uniform. It’s all about the edge!
Heeled ankle boots with straight-leg medium-wash jeans
Hedge ankle boots with a 1-2 inch chunky heel elevate any outfit. They look especially sleek with straight-leg jeans.
Choose boots in leather, suede or pleather with a rounded or pointed toe. Neutral tones like brown, black or tan work well.
Straight-leg jeans in a medium blue wash fall neatly without bunching into the boot shaft. The silhouette should be relaxed but not baggy.
Tuck in breton stripes, silk blouses or knit sweaters to showcase your great proportions. Neutrals keep the focus on the pants and shoes.
A blazer, trench coat or duster creates a stunning finish. Opt for complementary shades like navy, olive or gray.
Dangle earrings, a statement ring and crossbody bag accessorize with ease.
Heeled boots lift your confidence and walk while jeans feel laidback. Wear all day with comfort.
For unpredictable weather, swap heels for booties with small platforms or lug soles as needed. Style stays on-trend.
Smile as you strut down the street slaying in this effortlessly cool, head-turning yet oh-so-wearable ensemble!
The right boots can totally transform an outfit and your look.
