Stylish Summer Getaway Outfits

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Tropical escape, Wine Country, European beaches, Southern hospitality…June is the month of the summer getaway. So you know what that means? Time for some summer getaway outfit shopping!

Our editors have put together a great set of fits that’ll have you vacay’ing in style. Chic, yet simple and oh so perfect for making those “I have arrived” pics truly insta worthy.

Every minute of vacation time is precious, so our first fit will have you ready to go the moment you arrive. This flattering abstract floral print sheath dress is from Boston Proper’s Beyond Travel collection. It’s made of 4-way stretch material that won’t wrinkle even after hours in your seat. We pair this fit with equally travel-friendly accessories from Knockaround’s new arrivals, Hey Ube in their Panoramas frame. For keeping your items handy, the Dagne Dover Carryall has five internal pockets, an inside water bottle sleeve, and a separate laptop sleeve all in the size of a medium bag. It can be worn on the shoulder or as a crossbody and is made from super durable neoprene made from recycled plastic bottles. Finally, don’t forget your feet! Birkenstock’s Decon slip-ons takes all their cushy, contoured footbed technology and puts it into an easy slide on slipper silhouette that will have you breezing your way through security in style.

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Heading your way to wine country this summer? Oh the fun you’ll have in the California sunshine. Just remember that on average in the month of June, Napa is in the low to mid 80 degrees. Stress on the word average here, because more often than not it can soar up to the nineties. And it will be sunny. So channel your inner boho babe and dress appropriately. This crochet top plus an easy-breezy midi from Windsor is absolutely a splendid option. So light and airy and the chic neutral tone is fantastic. You’ll also want some comfy walking shoes as you head from winery, to art galleries, to Michelin star restaurants. Beek’s handmade toe ring sandals are made of vegetable tanned leather that will mold to your feet, giving you a totally bespoke shoe. Add Micas statement gold and pearl mega-earcuff earrings and a big, woven tote to carry all your found treasures in, and you are ready to rosé  all day.

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Maybe you’re less Monterey and more Martha’s Vineyards? June is a wonderful month to visit the New England states. There’s so much to see and to do, from beaches to sailing and island hopping. If this area is on your itinerary you’ll want to keep a few things in mind with your outfit. Think nautical meets Americana. This flowy, cutout sundress we found hits that vibe perfectly. Oh, and regardless of the temperature there, it IS going to be windy, so a hat is an absolute must. This cheery lavender bucket hat (yes, buckets are back for 2024) by Helen Kaminiski goes so sweetly with RAEN’s two-tone tortoiseshell and pink ivory shades. And since we’re by the shore, Donald Pliner’s raffia embellished thong sandal seems most appropriate, as does JW Anderson’s denim tote. You are ready for all the fun New England has to offer.

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Are the southern states calling your name? Then let’s get you a glass of sweet tea and a fit that’s sweet to match. Summertime along the southern coast means lots of live music, great food, warm sand beaches and lots of heat. When you’re not strolling along the boardwalk, you’ll most likely be hitting the beach, so consider an outfit that can cover a suit while still being restaurant and venue friendly. This aughties-inspo handkerchief top from Windsor understood the assignment. Easy on and off for the beach, your suit top will fit just fine underneath. For below, slide on a pair of Vans retro shorts. The fabric is light and airy with breezy wide legs (short but not cheeky) and made of fast-drying tech fabric. Pair it with one of our Editor’s favorites, Birkenstock’s Arizona essentials. Made from compression molded EVA, they are super soft, look amazing and are completely water-friendly. Grab some oversized Zenni shades and CalPak’s small-but-roomy sling bag and you are ready for southern sun and sand.

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Do this summer’s musical festivals have you singing their tune? This easy outfit is perfect for a myriad of venues. We start with Windsor’s super cute crop top in a sunny summer floral. We love how it pairs with one of Joe’s Jeans best sellers, their Double Buckle in Weightless. As the name implies, the dark wash is made from lightweight, warm weather denim…but with just a bit of stretch to keep things comfortable as you go from stage to stage catching your fav bands. On-trend Sambas with their ergonomic foot bed will feel as good as they look, and a pair of oversized Blender’s aviators round things out nicely. And since we’re talking about a true OOTD here which will most assuredly be your go-to for more than a few festies, save yourself time and anxiety trying to figure out if your bag is too big or too small and simply use Furla’s clear crossbody. It’s rated approved for pretty much every venue out there and comes with a removable woven inner bag (for non-fest times when you prefer some handbag privacy).

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Fancy a trip across the pond to enjoy the best of what the Mediterranean has to offer? Whether you’re meandering in Mykonos, beaching in Barcelona or spa’ing in Sardinia, this wide-leg jumpsuit we found is the jackpot. Light, breezy materials, flirty cutouts and the color is a real pop to your fit. To this we add Birkenstock’s newest sandal, the Almina, in super soft nubuck leather, that are ready to take on the streets in style. A mini sling bag from Dagne Dover will help alleviate any concerns milling through tight crowds. Knockaround’s Bob Marley wayfarers add seriously stylish fun, and finally a tiny touch of bling with Aurate NY’s 14k recycled gold earrings.

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Is it time to get tropical? If you’re hopping to Hawaii or heading somewhere south of the equator, you really need to dress for the heat and the humidity. The remedy? This maxi dress from Windsor is lightweight knit and open back, ensuring plenty of air exposure and less sticky material. Matisse’s Verona sandals will give you sure footing while keeping your feet cool, and Trina Turk’s breathable woven sun hat will have you smiling in the shade. Of course we couldn’t forget a bit of bling, so pop on a pair of thick frame Ray-Bans and Kendra Scott’s gorg pearl and gold statement earrings.

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Maybe you prefer to take your sunshine on the water and have a yacht’ing good time? This sultry blue-green mini dress from Windsor is made of mesh fabric, perfect for keeping you cool and chic. Bonus, its bodycon silhouette means those ocean breezes won’t be a worry either. When it comes to boats, and especially with yachts, there is an expectation that guests will understand the rules of footwear. Heels are frowned upon, both for safety reasons and because they can damage the teak flooring. Does that mean giving up looking stylish? Not at all. Cariuma’s low top canvas shoes are practical and pretty. Add some real bling to your fit with Satya’s gemstone and lotus anklet and a pair of oversized flower earrings by Baublebar. Nina’s natural straw clutch also adds a touch of sparkle, and we complete our sea worthy look with a pair of polarized aviators courtesy of Blenders.

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If vacay includes quality club time with your squad, this next fit is all for you. We combo color punch with serious bling, starting with Milly’s strapless sequined top and Windsor’s saturated coral, bandage mini skirt. Show off your fancy footwork with Nina’s chrome glazed embellished sandal (made for bridal wear, these shoes will easily stand up to the night). Dooney & Bourke’s candy pink crossbody is large enough to carry all your necessities hands free and we finish this look with some decadent drop earrings from Eye Candy LA.

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Tropical locals beg for dining al fresco. Skip the expected dinner dress and instead lean into this breezy jumpsuit. With a sleeveless plunging halter neckline and cutout bodice the looks reads lowkey sexy cool, while the wide-leg silhouette and stretchy smooth knit fabric will have you keeping your cool in the heat. Keep the tropical vibe going with natural textured accessories, like Coconut’s wood and crochet sandal, Hobo’s green woven clutch, and Cato’s wooden bead hoop earrings. All that’s left is to slide on Zenni’s oversized cateye sunnies, called appropriately enough, What’s New Pussycat.

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Finally, one of the most popular getaways for 2022 – the UK. Whether you’re saying cheerio in London, grabbing a pint in Ireland or marveling at the moors in Scotland, you should expect to dress for the unexpected…that being the weather. Generally speaking the temperatures are mild and comfortable, but the mornings and evenings can be a bit more chilly than you think for summer season. For this reason, you’ll want to focus on layers. We start with something fun and colorful, from the OG of gorg dresses, Diane von Furstenburg. This below the knee, green beauty looks picture perfect when paired with Paige’s Rowan jacket in medium blue. Give your feet a pick me up with a pair of mary jane Weejuns from G.H. Bass. Oh and also, the UK does have a habit of being rainy, so don’t forget to pack your umbrella. We’re big fans of the new reversible ones that let the water funnel away from you when closed.

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That’s our list! We hope you found some inspiration and maybe a few items to your shopping list. Wherever you decide to wander to this summer, we here at SLH wish you a safe and wonderful time!

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