Vacation Dresses & Outfits

Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.

Summer Vacation Dresses & Outfits Ready For Fun!

Get ready for fun with summer vacation dresses and outfits! Perfect for getaways, you'll feel stylish and confident in Windsor's updated collection. Whether you're planning a beach resort or a cabin by the lake retreat, we have the perfect ensembles to elevate your vacation style.

Plan your travel wear with matching clothing sets. Capture seasonally-inspired two-piece sets with tops, skirts, flow pants, shorts, and more. Mix and match crop tops with high-waisted skirts or linen wide-leg pants in neutral patterns or trendy tropical prints. These versatile pieces can be easily paired with sandals, straw tote bags, and sunglasses for a chic look!

Layering is key for vacations, so don't forget to pack lightweight sweaters and tie-front tops to transition your outfits from day to night. Explore our variety of sheer crochet sweaters or wear them with breezy tie-front tops to layer over a stylish jumpsuit or rompers. Add a touch of boho to your look with a statement belt, and top it off with a trendy hat for a complete head-to-toe resort wear look.

If you're heading to a picturesque destination or setting off for your honeymoon, embrace the bold colors and textures of the season. For a romantic dinner under the stars, opt for a floral print dress with tropical flowers or palms paired with flat sandals or sleek heels and a denim jacket for added warmth. Embrace the chic vibe with a bodycon midi dress in a bold abstract print, finished off with stylish lace-up heels, statement earrings, and a cute crossbody bag.

Immerse yourself in the soothing energy of being at a beach resort or cabin by the lake with an array of women's fashion trends featuring trendy crop tops, flirty mini skirts, bolero shrugs, or corset tops. Nail an effortlessly chic look by pairing your favorites with espadrille wedges perfect for exploring or enjoying a meal by the water. When the night falls, stand out under the starry night sky with a flowy, strapless maxi dress and faux pearl earrings. Complete the ensemble with statement heels and a chic clutch to carry your essentials.

Explore our collection of flirty floral and solid skater dresses with unique details like puff sleeves, lace-up backs, and ruching that accentuate your curves. Complete your look with adorable hair accessories, a crossbody purse, and stylish sandals. Don't forget to check out our new arrivals of jumpsuits and rompers, perfect for creating effortless vacation outfits.

We have you covered in-store and online for every occasion, ensuring packing is easy and styling is effortless. This season, turn to Windsor for all your vacation outfit ideas. Get ready to make a stylish statement wherever your 2024 adventures take you!

What Should I Pack For A Vacation?

What you pack for your vacation depends on the activities you’ll be doing and the climate of your destination. Starting with the essentials, pack staple pieces like basic tees, comfortable shoes, a casual dress, and high-waist jeans for fun activities like exploring a city or a staycation at your bestie’s house! Think about creating layers for when you need more or less protection for a specific activity, uncertain weather, and/or coverage from the elements. Choose lightweight long sleeve crop tops and dusters for warm temps and sweaters or open front trenches for colder destinations. If you’re heading to a warm climate, make sure to bring some stylish floral tops, cute sandals, stylish skirts, breezy sundresses, trendy cover-ups, denim skirts, and comfortable shorts. If you’re traveling to a colder climate, be sure to pack jackets, booties, beanies, scarves, and cozy chenille knit sweaters. For the days that you’ll dress up on your vacation, consider dressy and semi-formal attire like an LBD, skater romper, wrap satin dress, or velvet short dresses that you can pair with clear heels or rhinestone stilettos. The next time, you’re heading out for a vacation, think about the length of your stay, the activities you’ll encounter, and the weather of your destination.

Should I Pack For A Staycation?

Yes, you can totally plan and pack for a staycation. Changing up your clothes or getting excited about the fashions you love has the power to reframe your mindset. If you’re heading over to your bestie’s or bae’s place or staying a city over, packing for the occasion is a must! Use this time to experiment with your look and get in touch with your personal style again. Consider shopping for essentials like high-waist jeans, graphic tees, cute rompers, stylish loungewear, and pretty pajama sets to unwind. If you’re trying to keep it cozy at home, plan a cute outfit or loungewear set for each day, like a true diva. Consider a matching crop top and jogger set that is soft to the touch and trendy for going out exploring and relaxing until dinner. Style a ruched crop top with matching biker shorts and sneakers for a laid-back outfit that you can wear on any staycation. If you take time to plan staycation outfits, you'll get more excited about the different activities you have planned too. Dress up for dinner with a sleek, satin midi dress or plunging V-neckline jumpsuit styled with mules and your favorite jewelry. Finally, nail that supper cute look for running errands...just in case you're looking to capture the attention of a new bae while taking it easy. Dressing up for your staycation is a perfect opportunity for a photo shoot with the environment around you too so you can share your style and creativity on social media. Whatever you have planned for your time off, be sure to bring the style staples that make you feel like the best you!