Your winter jeans and boots don’t look off because of the trend — it’s a proportion issue. When denim width and boot shape compete, the outfit looks choppy. Straight or slim jeans pair best with ankle boots that tuck cleanly or leave a small gap. Taller boots work best with straight or skinny jeans tucked in for a smooth, uninterrupted line. I’ve linked the most flattering, wearable denim styles I reach for again and again in my Best Denim Edit on LTK → JeansAndBoots WinterStyling WomenOver35Style HowToStyleJeans JeansOutfitIdeas BootsOutfitIdeas ChicWinterStyle PolishedOutfits StyleTipsForWomen WinterBasics EverydayStyle LTKFinds LTKStyle LTKOver40 LTKSeasonal LTKgrwm

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Brinley Mid Rise Classic Straight Leg Jeans | Nordstrom
Aldo Vellamo Bootie | DSW
Dolce Vita Aldy Pointed Toe Knee High Boot (Women) | Nordstrom | Nordstrom
Women's Curve Love Ultra High Rise Ankle Straight Jean | Women's Clearance | Abercrombie.com | Abercrombie & Fitch (US)
AE Strigid Curvy Mom Jean | American Eagle Outfitters (US & CA)
Pocket Tote Bag | Anthropologie (US)
Legacy Pebble Leather Small Tote Bag | Macy's
Mongolian Cashmere Oversized Crewneck Sweater | Quince
Sylvia Knee High Boot (Women) | Nordstrom
Lauren Ralph Lauren Women's High-Rise Skinny Ankle Jeans - Macy's | Macy's
Bespoke High Waist Skinny Jeans | Nordstrom
Lauren Ralph Lauren Rexden Cable Stitch Sweater | Nordstrom | Nordstrom
Tommy Hilfiger Women's Traveling Cable Sweater - Macy's | Macy's
Textural Stitch Cable Crew Sweater | Abercrombie & Fitch (US)
VICI Collection Dreamer Cable Stitch Mock Neck Sweater | Nordstrom | Nordstrom