Vacation Dresses & Outfits | Resort Wear & Travel Outfits (2024)

Fall Vacation Outfits: Elevate Your Style for the Holiday Season!

Get ready to embark on your fall getaway with Windsor's collection of stylish women's vacation outfits. Whether you're planning a cozy cabin retreat or a city adventure, we have the perfect ensembles to elevate your fall vacation style.

If you're heading to a picturesque autumn destination or setting off for your honeymoon, embrace the rich colors and textures of the season with our fall-inspired two-piece sets. Mix and match cozy sweaters with high-waisted skirts or wide-leg pants in warm earth tones or trendy plaid prints. These versatile pieces can be easily paired with your favorite boots or booties for a chic and comfortable look.

Layering is key for fall vacations, so don't forget to pack lightweight jackets and cardigans to transition your outfits from day to night. Explore our variety of long dusters or kimono jackets to wear with your stylish jumpsuits or rompers. Add a touch of boho to your look with an open-weave crochet duster, and top it off with a trendy wide-brim hat.

For a romantic dinner under the stars, opt for a floral fall dress paired with ankle boots or sleek heels and a cozy knit cardigan for added warmth. Embrace the cozy-chic vibe with a bodycon midi dress and statement earrings, finished off with stylish ankle boots and a cute crossbody bag.

Immerse yourself in the vibrant energy of a bustling city like New York, Chicago, or San Francisco with a trendy crop top and skirt ensemble. Discover a variety of flirty mini skirts or sleek midi skirts that style perfectly with cozy sweaters or satin blouses. Nail an effortlessly chic look by pairing it with your favorite ankle boots or chunky sneakers, perfect for exploring or enjoying a coffee at a local café. When the night falls, shine under the city lights with a sleek satin blouse and high-waisted trousers. Complete the ensemble with statement jewelry and a chic clutch to carry your essentials.

Explore our collection of sleek satin dresses with unique details like thigh-high slits, lace-up backs, and ruching that accentuate your curves. Complete your look with statement earrings, a clutch, and stylish heels. Don't forget to check out our new arrivals of jumpsuits and rompers, perfect for creating effortless vacation outfits. We've got you covered for every occasion, ensuring packing is easy and styling is effortless. To elevate your fall vacation outfits, accessorize with the latest hats and chic hair accessories to complete your outfit of the day.

This season, turn to Windsor for all your fall vacation outfit ideas. Get ready to make a stylish statement wherever your 2023 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!