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

Vacation Outfits: Elevate Your Style for Spring Break and Summer Vacay!

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

If you're heading to a picturesque destination or setting off for your honeymoon, embrace the rich colors and textures of the season with our seasonally-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 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 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 spring break or summer 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 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!

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

FAQs

How should I dress when going on a trip? ›

Tips for Buying Comfortable Travel Clothes

That said, we recommend clothes made of soft, sweat-wicking, and breathable fabrics such as cotton, polyester, linen, or wool. It's also wise to opt for wrinkle-resistant materials like nylon and spandex to keep you looking fresh and put-together.

Can you wear a dress to travel? ›

My go-to flight attire is dresses, even in the wintertime. It helps me to feel comfortable, confident, and stylish when traveling. It's also practical for short-haul flights or flights where you will land in the morning.

What is vacation casual attire? ›

The styles you'll find in a resort casual or informal atmosphere are similar to what you'd find at popular breakfast and lunch spots. You can comfortably wear swimsuit coverups, jeans, capris, and shorts with a t-shirt or polo.

What is a resort dress? ›

Resort Casual Dress Code

You're probably scratching your head and wondering “what is resort casual?” If your destination has a beachy vibe, you'll probably sport a resort casual wardrobe. Think strappy dresses and gauzy cover-ups over your bathing suit, or cute shorts with a stretchy t-shirt.

How do I look classy when traveling? ›

Choose wrinkle-resistant fabrics that are comfortable, breathable, and easy to care for. Opt for basics like stretchy jeans, leggings or travel-friendly trousers as a foundation. Pair them with blouses, tops, or sweaters in neutral tones, allowing you to effortlessly create stylish ensembles.

What is the best type of clothing to travel with? ›

Neutral colors: Luggage space is precious. Ditch the bright colors and pack neutral—brown, black and khaki—especially for pants, shorts and skirts. These colors coordinate well with everything, so you can pack less. Wrinkle resistance: Look for garments touted as wrinkle-resistant.

How many clothes do I need for a week vacation? ›

I have a simple equation for a week of packing – three tops and three pants that all must match each other. This way I get nine outfits from six articles of clothing! Throw in a little black dress, and you're ready to take on any destination.

What is the resort chic dress code? ›

Resort Chic/Tropical Attire. Resort chic/tropical attire is casual and breezy but still has plenty of glamour. It means lightweight fabrics like cotton and linen. Men can opt for neutral colors paired with bright, tropical prints with boat shoes or loafers.

What dresses are considered casual? ›

Dresses: You can wear casual dresses that, similar to skirts, are at least knee-length. Depending on your workplace, you may choose to wear patterned or colorful styles or choose more traditional solid or neutral colors.

What do tourists dress like? ›

Dressing like a tourist is easy! A bright Hawaiian shirt is a classic look, but neon prints and souvenir t-shirts are also great shirt options. For bottoms, definitely go with khaki shorts or cargo shorts. Slip into a pair of white crew socks and strap your sandals over them to create an iconic tourist vibe.

What is a smart casual resort attire? ›

Resort casual Style may normally refer to polo style shirts, sundresses, linen pants, skorts, skirts, button up tops, nice shorts, and dresses. Nothing fancy, but not just t-shirts and jeans either. Do not wear cutoffs and tank tops for sure!

What do people wear at sandals? ›

Resort Casual: Shorts or jeans, t–shirts or polo shirts. Swimwear must be covered. Shirts and footwear required. Resort Evening: Dress pants or jeans for men, long or short sleeve dress shirts (with or without collar).

Which outfit is best for trip? ›

Wear a turtleneck sweater, put on some nice high-waisted jeans and wear a leather jacket or a long cardigan. Add some cool sneakers to this outfit and you are good to go! Wear a classic satin blouse with wide-leg jeans and put on some high heels or wedges. Trust me this look will make you look simply gorgeous.

How can I look beautiful while traveling? ›

9 quick tips to look fresh while traveling
  1. First and foremost is to hydrate. ...
  2. Moisturize your skin before setting forth on the journey. ...
  3. Your lips are also as important as the skin of your face: While traveling your lips are susceptible to crinkling and cracking.
Jan 16, 2018

What is best to wear on a plane? ›

Tips for What to Wear on a Plane

No one wants to sit through a seven-hour flight in constricting jeans or too-tight shoes — soft, stretchy, and stylish clothing is the way to go. Athleisure sets, loose-fitting pants and tops, and slip-on shoes all make for comfy and convenient plane outfits.

How many outfits do I need for 1 week trip? ›

Do the clothing countdown: If you need a mantra to help streamline your wardrobe, use the 5, 4, 3, 2, 1 rule for a weeklong trip: Limit yourself to no more than five sets of socks and underwear, four tops, three bottoms, two pairs of shoes and one hat. The list should be adjusted to suit your needs.

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