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Style Tips: Dressy Shorts

Our latest edition of Style Tips looks at the endless options for styling the latest separate du jour: dressy shorts. We’ve taken tips from Kate Moss, Chloe Sevigny and more!

While cocktail dresses and polished skirts have long been the go-to pieces for a picture-perfect party outfit, the surprising new separate du jour is a pair of dressy shorts. This super-flattering look has come a long way since its first appearance, thanks in part to early-adopters like Olivia Palermo and Kate Moss, and iconic brands such as Chloe, Prada and Dolce & Gabbana. Accordingly, if you’re looking to include a pair of dressy shorts in your next event ensemble, there are a slew of different styling options to choose from.

While fashion-forward femmes like Kate Moss and Chloe Sevigny opt for statement blazers and plenty of leg, starlets like Olivia Palermo and Margherita Missoni style their dressy shorts with flirty blouses and round-toed pumps. As you can see, the options are endless! Whichever direction you choose, we are sure you’ll find plenty of inspiration from the six chic celebs in this month’s edition of Style Tips.

#1. Pair your shorts with a structured blazer for a classic summer-ready ensemble: Given her status as one of the world’s most stylish women, it comes as no surprise that supermodel Kate Moss is leading the charge with her chic take on dress shorts. By pairing her shorts with wedges, a slinky top and a structured blazer (in a complementary color, natch), Kate has created a fresh look that is subtly sexy – think an updated, modern version of Diane Keaton’s Annie Hall. For a similarly stylish ensemble, start with Topshop’s Silk Drop Crotch Shorts ($60) or Anthropologie’s Terra Firma Shorts ($69.95). Add Barila’s Tencel Knot Top ($120) and a structured blazer – we like Oasis’s Double Breasted Blazer ($75.80) and Theory’s Bindi TS Blazer ($365).

#2. Mix textured shorts with a bold print for a bohemian-luxe look: Margherita Missoni is known for her confident gypset aesthetic and this outfit is no exception! We love how Margherita has played with textures and prints to create an ensemble perfect for an exotic party, a fashion show or a day out shopping in Milan. To recreate her look, start with a pair of printed shorts with textured fabric or bold details – we like Anna Sui’s Ethno Print Shorts ($152.84) and Vena Cava’s Dorze Shorts ($192.50). Then, simply add a loose blouse, such as Joie’s Martine Blouse ($198) or Rachel Roy’s Tailored Shirt ($397.50), and neutral pumps –Colin Stuart’s Round-Toe Platform Pumps ($49) are ideal.

#3. Give your dress shorts a low-key twist by adding a simple tee to the mix: Actress Cameron Diaz has an athletic body, by nature – as such, dress shorts are a great way to show off her physique while looking fun, feminine and flirty. While her outfit has several polished elements, such as a fitted blazer and suede wedges, she has kept it low-key by throwing on a simple white tee. The result? An outfit that stays true to Cameron’s sporty-yet-chic aesthetic. If you love this look, grab Topshop’s Tailored Shorts ($100) and layer them underneath your favorite white tee. Then, throw on Dallin Chase’s Giovanni Blazer ($106) and a pair of edgy suede wedges – we like J Crew’s Dorian Wedges ($238) and L.A.M.B.’s Zane Wedge Sandals ($135.85).

#4. Soften a pair of knit shorts with a lightweight, sheer blouse and simple pumps: Reality star Olivia Palermo is always perfectly put-together, with nary a hair out of place; happily, she achieves this refined appearance by mixing contemporary pieces with classic designers. Here, she balances a pair of heavy, knit shorts with a sheer, lightweight blouse – the result is perfect for a low-key office setting or an after-hours cocktail. For an equally chic combo, layer Rachel Roy’s Classic Skorts ($89) underneath a sheer blouse – Elizabeth and James’s Aimee Blouse ($265) is ideal. Finish off your look with Joan & David’s Flipp Platform Pumps ($139.99).

#5. Dress up denim with a feminine blazer and a cute clutch: We admit it – we cheated a little with our next pick. While actress Chloe Sevigny is actually wearing fitted denim shorts, they take on a more polished appearance when paired with chic attire like a scalloped blazer, smart clutch and ankle boots. The overall effect is polished and pretty, with a little edge. To take a leaf out of Chloe’s book, start with a flirty jacket like Nanette Lepore’s Rescue Me Jacket ($398) or La Rok’s Vintage Cigarette Jacket ($258). Complete your ensemble with your favorite denim shorts, Nine West’s Palomar Ankle Boots ($98.95) and Rebecca Minkoff’s The Clutch ($330).

#6. Play with color by using soft pastel shades and touches of grey: It isn’t a surprise to see reality star/designer Whitney Port incorporate various pastel shades into her look – after all, she has never been afraid of color. However, as Whitney demonstrates, there is a trick to wearing colorful dressy shorts: wear muted or low-key versions of your favorite shades, whether you go for pastels or darker tints. For a stylishly subdued look like Whitney’s, pair AllDressedUp’s Ruched Cotton Shorts ($79.50) with a soft blazer like Asos Black’s Pearl Shoulder Waterfall Blazer ($185.30) or Asos’s Dipped Hem Silk Blazer ($33.69). Throw on a grey tee and a pair of metallic sandals and you are good to go.

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