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

Which outfit is best for trip? ›

Generally soft, stretchy, and loose-fitting clothing is best for travel, as it'll keep you comfy and won't feel restrictive on long flights or drives.

How do I look classy when traveling? ›

Classic Jetsetter. For a timeless yet effortlessly chic look, opt for a pair of high-waisted jeans paired with a basic tank. Layer with a cozy cardigan or smart blazer for chilly airplane cabins. To accessorize, you can't go wrong with a sleek leather tote and a silk scarf.

What is the resort casual dress code? ›

Resort Casual

You can comfortably wear swimsuit coverups, jeans, capris, and shorts with a t-shirt or polo. Tennis shoes, sneakers, and sandals, are all acceptable as well. You can even wear flip flops with this relaxed dress code!

What should a woman 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.

What should I wear on a 2 week trip? ›

Capsule Wardrobe for a Two Week Vacation
  • 7x tops (or five tops plus two dresses)
  • 3x trousers, skirts, or shirts (depending on weather and preference)
  • 2x outerwear items for layers.
  • 2-3x shoes.
  • 7-10x underwear (allow a few extra pairs for the days while you're getting your laundry done)
  • 1x bathing suit (if needed)
  • 1x scarf.
Nov 25, 2020

How to dress to look rich and classy? ›

Always wear clean clothes, freshly pressed, with no threads, rips, stains, or fading. Black, white, navy are always elegant colours that can make you look more expensive. Match your outfit with some assorted accessories such as a couple of bracelets and a pair of sunglasses for that extra visual effect.

How to look hot and classy? ›

Define your waist and wear balanced looks to be classy but sexy, like pairing a short skirt with a top that has longer sleeves or a higher neckline. Choose colors that compliment you, like dark purples and greens for cool skin tones, metallics for warm skin tones, and bright colors for neutral skin tones.

What is resort dress code for ladies? ›

Casual dress

It is important to avoid anything too revealing or sloppy in appearance. Flip flops and athletic wear should also be avoided. Casual attire is appropriate for most activities during a resort vacation, such as dining at restaurants or lounging by the pool.

What is resort casual attire for a woman? ›

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 is smart casual dressing? ›

Smart casual is professional but a little relaxed - a polished take on more casual pieces of clothing as well as casual or fun items paired back with smarter pieces. Items are typically less structured and the formality downgraded from traditional corporate wear.

How many outfits for a 7 day trip? ›

Pack complimenting clothing.

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.

How many outfits for a 5 day trip? ›

Pack enough clothes to last you the week.

For a 5 day vacation, you will want to bring 2-3 pairs of shorts or pants, 3-4 tops, a light jacket (or a heavy jacket, depending on where you are traveling), and 1 formal outfit if you are planning on attending a nice restaurant or event.

How do you travel with dresses and suits? ›

The stash-in-bag method

Co-owner Tali Gallo said their go-to method is placing the dress inside a garment bag, taking the hanger out, removing as much air as possible and rolling it up gently to fit into a hard-shell carry-on bag. Take care not to roll the bodice if it has boning, she said.

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

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.

How to pack for a 5 day trip? ›

What to pack for a 5-day trip checklist? (Things to put )
  1. Clothes that you can use for Five Days. ...
  2. Comfortable shoes that you can wear the Whole Day. ...
  3. Disposal shower cap to keep your Bag Clean. ...
  4. Comfy nightwear for your Trip. ...
  5. Slippers for your Extra Comfort that you want to Have.

How many clothes do I need for a 5 day trip? ›

For a 5 day vacation, you will want to bring 2-3 pairs of shorts or pants, 3-4 tops, a light jacket (or a heavy jacket, depending on where you are traveling), and 1 formal outfit if you are planning on attending a nice restaurant or event. If you are going to the beach, pack 2-3 swimsuits/trunks.

How many outfits should I bring for a 3 day trip? ›

Pack three outfits, three pairs of underwear (an extra pair or two never hurts), one set of pajamas and three pairs of socks. If you're planning on going out to dinner at least once on your trip, consider bringing an additional outfit that is better suited for a restaurant than your typical comfortable clothes.

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