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How To Wear Women's Shorts In Fall & Winter

As you transition into fall, style up in the trendiest shorts in chic fabrications and colors! Shop Windsor for outfit inspo to create the best autumn looks. Choose from casual and dressy shorts to take you from day to night in a variety of styles to suit your fashion mood.

If the weather is still warmer where you live, pair your fave denim shorts with cropped sweaters, cardigans, and long sleeve tops, and bodysuits for every day. Style these looks with ankle booties, combat boots, or classic sneakers to keep it casual. Discover chic woven shorts with belted waists or tie-front accents that level up trendy graphic tees. Take these shorts from day to night by trading your basic bodysuits for stylish crop tops or blouses and leveling up the looks with heeled mules. Go from the office to happy hour with the cutest paperbag shorts paired with cropped blouses and boyfriend blazers. Shop Windsor’s selection of paperbag shorts in the best neutral hues that will pair with all of your outfits including black, white, tan, and beige. Amp up your outfits for fall nights out with sleek faux leather shorts. Swap out your skirts for edgy faux leather shorts to style up for dates or nights out on the town.

Explore chic faux leather shorts with pockets, tie-fronts, or paperbag waist designs. Creating a DIY look for Halloween? Opt for sexy form-hugging faux leather red bottoms or sultry lace-up shorts with cheeky fits. Elevate your loungewear ‘fits with trendy biker shorts in stretchy and comfortable knit fabrics. Style with crop tops, shackets, and sneakers for running errands, or blazers or moto jackets and mules for drinks with the girls. Find the cutest assortment of cozy shorts to relax in, like high-waisted shorts with soft fleece fabric and adjustable drawstring waists for customized fits. Pick these cozy styles for comfortable honeymoon outfits for a snowy getaway. For a stylish dress alternative for dates, parties, or autumn photoshoots, shop shorts rompers. Discover adorable plaid short rompers perfect for back-to-school attire paired with denim jackets and booties. Explore glitter knit rompers and basic woven rompers with fitted high waists and flared-out silhouettes for a figure-flattering look. Shop Windsor’s stylish selection of women’s shorts in chic and dressy styles to create the best looks this season.

Are Shorts Only A Casual Style?

Shorts are usually seen as a casual style, but they can also be dressed up and fashionable. Shorts with certain features like paper bag waists, tie-front accents, high-rise waists, button-front detailing, or chic fabrics like faux leather can definitely be worn to dressier events such as parties or for a date night. Romper shorts or rompers with a shorts design are a super cute style that you can wear to more dressy occasions and still provide the comfort and fit you look for in women's shorts.

What Are The Different Types Of Women's Shorts Styles?

The different types of women’s shorts styles include jean shorts, loungewear shorts, dressy shorts, and vacation shorts. Jean shorts can come with distressed or cut-off detailing to create boho to classic Americana looks. Loungewear shorts, such as biker shorts, tend to have soft fabrics like velvet, ribbed knit, or cotton blends for comfortable wear during those busy or on-the-go days. Dressy shorts are all about the fabric from faux suede to faux leather, satin to chiffon. These styles are great for bridal showers, date night, or creating a dressy look without having to wear pants, skirt, or dresses. The best vacation shorts tend to have a more relaxed fit and come in flowy florals, with flirty ruffles or have convenient cargo detailing so you can be prepared for any adventure. Cute short sets with matching crop tops are also popular year-round.