12 Fall Outfits With Boots: Stylish and Cozy Looks You’ll Love
Brrr… can you feel that crisp autumn air? Fall is here, and you know what that means time to break out those boots and layer up in style! Whether you’re a fan of ankle boots, knee-highs, or rugged combat boots, I’ve got 12 fall outfits with boots that’ll keep you looking chic while staying cozy.
As someone who lives for fall fashion (and owns way too many boots, IMO), I’ve tested tons of combos. From pumpkin spice latte runs to weekend apple picking, these outfits are perfect for every autumn occasion. So, grab your favorite pair of boots, and let’s dive in!
1. Classic Jeans & Ankle Boots Combo
There’s a reason why skinny jeans and ankle boots are a fall wardrobe staple—they’re timeless, versatile, and ridiculously easy to style. Whether you’re running errands or meeting friends for coffee, this combo keeps you looking put-together without much effort.
Ankle boots, especially in neutral shades like black, tan, or taupe, pair seamlessly with any denim wash. For a sleek look, tuck your jeans into the boots. If you prefer a more relaxed vibe, cuff the hem just above the boot opening. The key is balance—pair fitted jeans with chunkier boots or slouchy jeans with sleeker boot styles.
How to Style This Outfit
- Top: A chunky knit sweater or fitted turtleneck keeps you warm while adding texture.
- Outerwear: A tailored wool coat or oversized blazer elevates the look.
- Accessories: A crossbody bag and delicate gold jewelry add polish.
- Pro Tip: If your boots have a heel, opt for a slightly cropped jean to avoid bunching.
2. Oversized Sweater Dress & Knee-High Boots
Few outfits scream fall glam like a sweater dress and knee-high boots. This combo is effortlessly chic, keeping you warm while highlighting your silhouette. The best part? It works for so many occasions brunch, date night, or even a casual day at the office.
When choosing a sweater dress, go for a ribbed or cable-knit design in autumnal hues like camel, gray, or cream. The slightly oversized fit adds comfort while maintaining elegance. Knee-high boots in suede or leather with a low block heel elongate your legs while providing stability.
How to Style This Outfit
- Dress: Opt for a neutral-toned, midi-length sweater dress.
- Boots: Suede or leather knee-highs with a 2-3” heel are ideal.
- Extras: Add a thin belt to cinch the waist and sheer tights if needed.
- FYI: Pair with a long coat for extra warmth during chilly evenings.
3. Leather Jacket, Skinny Jeans and Combat Boots
Nothing says “cool girl autumn” like throwing on a leather jacket with combat boots. This combo has been a street style favorite for years because it’s the perfect mix of tough and feminine. The secret? It’s all about playing with proportions and textures.
Start with a fitted leather jacket whether real or faux, choose one that hits at your waist. Pair it with black skinny jeans (the stretchier the better for all-day comfort) and your favorite chunky combat boots. Pro tip: Go for boots with some hardware details like buckles or metallic eyelets to amp up the edge factor.
How to Style This Outfit
- Top Layer: A cropped leather moto jacket (bonus points for quilted detailing)
- Base Layer: A slinky turtleneck or graphic band tee for contrast
- Bottoms: Jet black skinny jeans with some stretch
- Footwear: Platform combat boots with 1-2″ soles
- Accessories: A chain-strap crossbody and hoop earrings
- Pro Tip: Cuff your jeans once to show off the top of your boots
4. Plaid Skirt & Over-the-Knee Boots
Channel your inner private school chic with this plaid skirt and OTK boots combo that’s equal parts sophisticated and flirty. This look works amazingly for everything from office days to weekend brunches just adjust your layers based on the occasion.
The magic happens when you pair a wool plaid mini or midi skirt (burgundy and navy plaits are especially autumnal) with suede over-the-knee boots. The boots keep you warm while showing just the right amount of leg. For work, go with a midi length skirt. For weekends, a mini skirt with tights keeps it playful.
How to Style This Outfit
- Skirt: A-line wool plaid in classic colors
- Top: Fitted turtleneck or crisp button-down
- Boots: Suede OTK boots with a low block heel
- Outerwear: Tweed blazer or wool coat
- Extras: Knee-high socks peeking over boots
- FYI: Add tights in “barely black” for chilly days
5. Cozy Cardigan, Leggings & Chelsea Boots
We all have those days when we want to be cozy but don’t want to look like we rolled out of bed. Enter: the oversized cardigan with leggings and Chelsea boots combo. It’s the sartorial equivalent of a warm hug while still looking Instagram-worthy.
The key is choosing luxe-feeling basics. Your cardigan should be chunky and oversized (but not swallowing you whole), your leggings should be high-waisted and squat-proof, and your Chelsea boots should have a slight heel for polish. Stick to neutral tones like cream, camel, or gray for maximum versatility.
How to Style This Outfit
- Cardigan: Oversized knit with ribbed detailing
- Leggings: Buttery-soft, high-waisted black leggings
- Boots: Waterproof Chelsea boots with almond toe
- Top: Longline tank or bodysuit underneath
- Accessories: Pendant necklace and oversized tote
- Pro Tip: Add a belt bag over the cardigan to define your waist
6. Denim Jacket, Midi Dress & Western Boots
This unexpected trio combines feminine florals with rugged Western details for a look that’s equal parts free-spirited and put-together. The contrast between the flowy dress and structured denim jacket creates visual interest, while the boots ground the outfit with rustic charm.
Choose a midi-length dress with autumn-appropriate prints like moody florals, paisley, or abstract watercolor designs. The denim jacket should be classic blue wash (distressed details add character) and hit at your natural waist. As for the boots, opt for authentic Western styles with stitching details and a comfortable 1-2″ stacked heel they’re surprisingly walkable!
How to Style This Outfit
- Dress: Flowy chiffon or viscose midi with long sleeves
- Jacket: Medium-wash denim with raw hem details
- Boots: Leather Western boots or cowgirl boots with angular toes
- Layering: Add a cropped sweater vest for extra warmth
- Accessories: Turquoise jewelry and ahttps://luxvibestyle.com/fall-outfits-with-cowgirl-boots/ slouchy suede bag
- Pro Tip: Knot your jacket at the waist to define your silhouette
7. Turtleneck, Trousers and Lug-Sole Boots
Who says workwear has to be boring? This power combo takes your standard office attire and gives it a serious style upgrade. The magic lies in mixing polished tailoring with chunky utilitarian boots it’s the perfect balance of professional and fashion-forward.
Start with high-waisted wide-leg trousers in wool or crepe fabric (they drape beautifully). Pair with a fitted turtleneck in a complementary color think camel trousers with black knit, or gray pants with cream sweater. The lug-sole boots should have enough chunk to make a statement but still look refined avoid hiking-style boots and opt for sleeker designs.
How to Style This Outfit
- Top: Thin merino wool turtleneck for all-day comfort
- Pants: Tailored wide-legs with front pleats
- Boots: Patent leather lug-sole ankle boots
- Outerwear: Longline wool coat or structured blazer
- Accessories: Minimalist watch and structured tote
- FYI: Tuck your turtleneck in fully for maximum polish
8. Puffer Vest, Flannel & Combat Boots
This outfit is the sartorial equivalent of pumpkin spice warm, comforting, and quintessentially fall. It’s ideal for those transitional weather days when you need adaptable layers. The combination of textures (quilted puffer, soft flannel, rugged boots) creates depth and visual interest.
Begin with a fitted thermal or long-sleeve tee as your base. Layer an unbuttoned flannel shirt over it classic red/black buffalo check never fails. The puffer vest adds warmth without bulk (go for cropped length to avoid overwhelming your frame). Finish with distressed jeans and your favorite broken-in combat boots for that perfectly lived-in vibe.
How to Style This Outfit
- Base Layer: Fitted heat-tech long sleeve in neutral tone
- Mid Layer: Unbuttoned flannel with sleeves rolled up
- Outer Layer: Quilted nylon puffer vest
- Bottoms: Lightly distressed skinny or straight jeans
- Footwear: Scuffed leather combat boots
- Pro Tip: Add a beanie and fingerless gloves for extra cool points
9. Midi Sweater Skirt & Block-Heel Booties
This outfit proves you don’t have to sacrifice warmth for style. The sweater skirt and booties combo is winter-ready while maintaining a dressy vibe perfect for holiday parties or date nights. The secret is choosing luxe fabrics that elevate the casual sweater material.
Look for a ribbed or cable-knit skirt that hits at mid-calf length this is universally flattering. Pair with opaque tights in black or dark brown for seamless coverage. Your booties should have a substantial but walkable heel (2-3 inches) in a complementary neutral shade. A cashmere turtleneck tucked in completes the luxe look.
How to Style This Outfit
- Skirt: High-waisted ribbed knit with side slit
- Top: Thin cashmere turtleneck in coordinating color
- Boots: Pointed-toe suede booties with block heel
- Hosiery: 80-denier opaque tights
- Accessories: Structured mini bag and delicate jewelry
- Pro Tip: Add a slim belt at your natural waist for definition
10. Corduroy Pants, Blazer & Ankle Boots
This outfit brings 70s vibes into modern day with its mix of textured fabrics and tailored silhouettes. Corduroy’s resurgence makes it perfect for fall, and when paired with sleek ankle boots, it strikes the ideal balance between vintage and contemporary.
Choose wide-leg corduroy pants in autumnal shades like rust, olive, or caramel the wider wale (ribs) are more on-trend. Your blazer should be structured but not stiff wool or tweed fabrics work beautifully. For the ankle boots, opt for a sleek leather pair with minimal hardware to keep the focus on the interesting textures.
How to Style This Outfit
- Pants: High-waisted wide-leg corduroys
- Top: Silk blouse or fitted turtleneck
- Blazer: Single-breasted wool with notch lapels
- Boots: Leather Chelsea or side-zip ankle boots
- Accessories: Tortoiseshell sunglasses and leather belt
- FYI: Cuff pants once to show off boot details
11. Blanket Scarf, Jeans & Riding Boots
This outfit is like a warm hug on a chilly day. The blanket scarf provides serious coziness factor while the riding boots keep it polished. It’s the perfect formula for weekend errands, apple picking, or casual Friday at the office.
Your scarf should be oversized (at least 30×70 inches) in an autumnal plaid or houndstooth pattern. The jeans work best in a dark wash or black they create a sleek base for the voluminous scarf. Riding boots should hit just below your knee look for ones with minimal branding and clean lines.
How to Style This Outfit
- Scarf: Wool-blend plaid in rust/cream/navy tones
- Top: Thin turtleneck or chambray shirt
- Jeans: Dark wash skinny or straight leg
- Boots: Leather riding boots with slight heel
- Outerwear: Wool pea coat or teddy bear jacket
- Pro Tip: Drape scarf asymmetrically for visual interest
12. Athleisure Joggers & Platform Boots
Who says you can’t be comfy and cool? This joggers and platform boots combo takes casual to fashion-forward territory. It’s perfect for running errands in style or casual weekend hangouts when you want to look put-together without trying too hard.
Choose high-waisted joggers in a luxe fabric like French terry or velour they elevate the look beyond basic sweats. Your platform boots should have chunky soles (1.5-2 inches) but avoid going full-on goth platform. Keep the top half fitted to balance the volume of the pants and boots.
How to Style This Outfit
Joggers: Tailored fit with tapered ankles
- Top: Cropped hoodie or fitted sweatshirt
- Boots: Chunky sole combat or hiking-style boots
- Outerwear: Oversized denim jacket or puffer
- Accessories: Bucket hat and crossbody bag
- Pro Tip: Cuff joggers once to showcase boots
Final Thoughts: Mastering the Art of Fall Boot Outfits
As we wrap up this style guide, let’s reflect on why boots are the ultimate fall wardrobe heroes. They’re not just practical for cooler weather they’re transformative pieces that can elevate any outfit from basic to breathtaking. Whether you’re drawn to the rugged charm of combat boots, the sophistication of knee-highs, or the effortless cool of ankle boots, there’s a perfect pair (or five) waiting to become your autumn signature.
Why These Outfits Work?
- Versatility: Every look transitions seamlessly from day to night, work to weekend.
- Comfort Meets Style: No sacrificing coziness for fashion here. These outfits are designed to feel as good as they look.
- Layering Potential: As temperatures drop, simply add tights, swap lighter tops for chunky knits, or throw on a longer coat.
Pro Styling Tips to Remember
- Play with Proportions: Balance oversized sweaters with slim boots, or flowy skirts with chunky soles.
- Invest in Quality Basics: A great pair of boots deserves equally great staples (well-fitting jeans, tailored blazers, cozy knits).
- Don’t Shy Away from Color: While neutrals dominate fall, rich hues like burgundy, forest green, or mustard make boots pop.
FAQs
Q: Can I wear white boots in fall?
A: Absolutely! Pair cream or off-white boots with neutral outfits for a fresh take on autumn dressing.
Q: How do I transition boot outfits from fall to winter?
A: Simply add tights, layer thermal tops underneath, and swap lighter jackets for wool coats or puffers.
Q: What’s the most versatile boot style to invest in?
A: A sleek black ankle boot with a 2-inch heel it dresses up or down effortlessly!
