Yes, you can wear a denim maxi skirt in the winter. Wearing a large in the blazer for an oversized fit, a medium in the shirt, and 4 in the skirt and an 8 in the kitten heel knee high boots

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Lapels houndstooth suit blazer -  Women | Mango USA | MANGO (US)
Heavyweight Wool-Blend Blazer Coat | Abercrombie & Fitch (US)
Oversized blazer | H&M (US + CA)
HIDDEN JEANS Front Slit Denim Midi Skirt | Nordstrom | Nordstrom
Denim Criss-Cross Waistband Maxi Skirt | Abercrombie & Fitch (US)
Denim Skirt - Denim blue - Ladies | H&M US | H&M (US + CA)
Denim Skirt - Light denim blue - Ladies | H&M US | H&M (US + CA)
Amazon Essentials Men's Regular-Fit Long-Sleeve Casual Poplin Shirt | Amazon (US)
JASGOOD Women Leather Belt for Jeans Pants Gold Buckle Lady Casual Dress Waist Belt | Amazon (US)
wetkiss Knee High Boots for Women, with Stiletto Heel and Pointed Toe Design, Classic and Sexy | Amazon (US)
Rosebery Leather Belt | Nordstrom
Chunky Gold Hoops Earrings for Women Thick 18K Real Gold Plated Open Hoop Lightweight Hollow Earr... | Amazon (US)
18K Gold Ring | WATERPROOF | Gold Band Ring | Thin Thick Gold Ring | Stacking Ring | Wedding Enga... | Etsy (US)
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