10 Best Ankle Boots To Wear With Skinny Jeans of December 2025

• Rolled cuff hem skinny with functional pockets and belt loops changes from a crop to an ankle length jean with ease, so you can pair with any trendy footwear from boots to sandals for use during all seasons
• The stretch denim fabric moved with you for that all around comfort no matter what your activities are
• Skinny rolled up is a 26 inch inseam and unrolled is a 27 1/4 inch inseam
• Jessica Simpson is an iconic American brand, offering fashion forward product with a compelling price value

Jessica Simpson

• With every pair of shoes you purchase, TOMS will give a new pair of shoes to a child in need. One for one
• Cotton twill sock liner

TOMS

• Be Energized insole with all-day comfort, cushioning and shock absorption designed to reduce foot pressure & fatigue
• Lace-up front and inside zip closure
• Faux shearling on tongue and collar
• Soft microfiber lining

Dr. Scholl's Shoes

• The LifeStride® Andrea ankle booties are the perfect complement to your favorite skinny jeans.
• Man-made upper features an almond toe.
• Side-zip closure.
• Rope accent around the ankle.
• Man-made lining. Velocity with Memory Foam® footbed provides cushioning and conforms to the shape of your foot.Block heel.Man-made outsole. Imported.Measurements: Heel Height: 1 1⁄4 in Weight: 11 oz Shaft: 4 in Product measurements were taken using size 7.5, width M (B). Please note that measurements may vary by size.Weight of footwear is based on a single item, not a pair.

LifeStride

• Super stretch lasts from day to night; Snug fit doesn't lose shape
• Vintage, worn-in look
• Mid-rise comfort waistband
• Skinny through hip and thig; Skinny leg opening
• 29.5" inseam, 5-pocket styling
• Unique fabric varies in color due to wash, finish, and dye
• Machine wash

Signature by Levi Strauss & Co. Gold Label

• Be Energized insole with all-day comfort, cushioning and shock absorption designed to reduce foot pressure & fatigue
• Slip-on fit with stretch twin gore panels for extra flexibility
• Micro suede upper

Dr. Scholl's Shoes

• With every pair of shoes you purchase, TOMS will give a new pair of shoes to a child in need. One for one
• Canvas sock liner

TOMS

• ESSENTIAL SHOE FOR YOUR CLOSET: Stay stylish and comfortable with this on-trend three-season staple, which has been made in versatile neutrals, rich jewel tones, and of-the-moment pastels to pair perfectly with your everyday outfits, whether you're keeping it casual or dressing up!
• COMFORTABLE & EASY ON/OFF: Lightweight silhouette with chunky heel and lightly padded footbed for all-day walkable wear; back zip for effortless functionality and adjustable buckled crossover straps for a perfect fit
• VEGAN: Durable and animal-friendly, this ankle boot features man-made materials throughout
• MEASUREMENTS: Approx. 3" chunky heel
• Imported

Cambridge Select

• FASHION FORWARD: Striking the perfect balance between the perfect balance between dressy and casual, this fitted ankle boot. Inspired by the latest sock boot trend, this rendition hits just below the calf.
• MAN-MADE MATERIALS: These fashion forward sock-boot inspired boots are made from 100% man-made materials.
• MEASUREMENTS: Heel: 3.75". Shaft: 5".
• WHERE TO WEAR: Ideal for desk-to-dinner, this ankle boot silhouette is versatile for everyday. Dress it up or style it down, it can accent pencil skirts, boho dresses, skinny jeans and any hemline in between!
• STRETCH ANKLE & ZIP CLOSURE: Inside zip closure remains virtually unseen, while the stretchy, elastic backed ankle hugs your leg for a feels-like custom fit.

ALDO

• ·For over 155 years, Frye's iconic boots have defined eras, embodied social movements, outlasted trends and defied time. Frye captures the essence of timeless American style - the promise of a dream.
• ·STYLE AND DESIGN: Authentically American, the Sabrina is durable yet flattering. A classic work boot with a Goodyear welt construction, combined with a slim ankle and mid heel. Crafted in luxurious leathers and colors. Made in the USA.
• COMFORT: Cushioned leather foot bed for all day wear.
• ·PERFECT FIT: Medium width and true to size

Frye