1. The easiest way to wear a skater skirt and stay warm is too add cozy tights, a cardigan, a sweater, and a hat. Wear oxford shoes to give your outfit a preppy vibe. 2. Wear a leather jacket with your skater skirt to toughen up the look. 3. Tuck a button-down shirt into your skirt and add a pair of ankle boots for a sophisticated outfit. 4. Wear a skirt and sweater with hi-top sneakers for a more casual vibe. 5. On less chilly days, forgo tights for thigh-high boots. Add a beanie and thick turtleneck to stay warm. 6. Thigh-high socks are also a great option if you don’t want to wear tights. 7. Wear your skirt with boots and a graphic tee, and add an open plaid shirt for a more grunge look. 8. Your shirt doesn’t have to be fitted to wear it with a skirt. Front tuck a loose, drapey shirt so it doesn’t look too bulky. 9. Go for a velvet skater skirt for a really wintery vibe. 10. Throw on a fur vest and floppy hat for a seriously trendy outfit. 11. Go for lots of layering: high socks, tights, boots, a turtleneck, a plaid shirt, and a jacket. 12. Wear your skirt with a graphic tee and combat boots for a casual and comfy outfit. 13. Wear a fitted blazer over a sweater. It’s a preppy, polished outfit that will definitely keep you warm. 14. Toughen up a feminine skater skirt with a studded sweater, embellished combat boots, and these cool stockings. 15. A cropped sweater goes perfectly with a high skater skirt. Add ankle boots for some height. 16. Wear thigh-high boots over your tights to stay extra warm. 17. Your sweater doesn’t have to be tucked in – leaving a bulky sweater hanging over a skater skirt gives you kind of a cool, boho vibe. 18. Add a trendy Panama hat and chunky knit cardigan to stay cozy. 19. Patterned tights like these make for a whimsical outfit. 20. Layer a sweater over a plaid shirt and let the collars and sleeves peak out for a schoolgirl-inspired outfit.