Home • Fashion Celeb Style: Winter Shorts Celeb Style: Winter Shorts By Essence · Updated October 29, 2020 01 Haute Shorts Celebrity choreographer Laurie Ann Gibson winterizes her shorts with thigh-high red studded boots. 02 Haute Shorts Sparkles and a bow add a holiday vibe to shorts in winter. 03 Haute Shorts A bold belt adds a pop of color to Keyshia Cole’s winter shorts. 04 Haute Shorts A loose fitting blouse, like the sparkling one worn here by Thandie Newton, makes a great compliment to shorts in winter. 05 Haute Shorts Bold floral details in Rihanna’s matching shorts and sweater set make shorts feel more dressy in winter. 06 Haute Shorts Dare to go there by spicing up a short romper, like Willow Smith’s, with a bold accessory. 07 Haute Shorts Long over the knee socks and a long draping sweater balance out shorts in the winter. 08 Haute Shorts Ciara layers a hoodie and structured jacket over her leather shorts to make them cool for cold weather. 09 Haute Shorts Winter booties, woolen tights and a warm leather jacket are perfect elements to warm up your shorts in winter. 10 Haute Shorts Designer Rachel Roy looks effortlessly chic as she pairs a long printed coat with booties to glam up her winter shorts. 11 Haute Shorts Vanessa White opts for shorts that hit mid thigh, which work well for cooler weather. 12 Haute Shorts Jessica Szhor’s wool paneled shorts are the perfect shorts for cold weather. Take notes and wear yours with a blazer and tank combination too. 13 Haute Shorts A knit blazer and dark accessories are the perfect way to bring shorts, like Kim Kardashian’s high waist version, into cool weather. 14 Haute Shorts Embellishments, like the studs on Keri Hilson’s hot pants, make shorts ideal for more glam functions and parties. 15 Haute Shorts Monochromatic layering, like Alicia Keys’ all-black-ensemble, make shorts more appropriate in cool weather. 16 Haute Shorts Warm, fall tones like the greens and browns in Jada Pinkett-Smith’s outfit, make ideal colors for winter shorts. 17 Haute Shorts Ciara takes a turn for the glam by pairing a dramatic fur and knee high suede boots with these wool shorts. 18 Haute Shorts Queen of shorts, Meagan Good can teach us a thing or two about shorts in winter: like wearing over tights with thigh-high boots. 19 Haute Shorts Nicole Ritchie selects the perfect winter short: high-waist, velvet version which works wonderfully when worn with tights and a cape. 20 Haute Shorts Turtleneck, thigh-high and tights, like Wendy Williams’ wears, are the classic way to extend your shorts from summer to winter. 21 Haute Shorts Corrine Bailey Rae shows the quirkier side of winter shorts with a fun print worn over netted stockings.