Sashay Vacay: The Cutest Vacation Outfits – Sozy

MY SHOPPING CART

HOLIDAY SALE - 25% OFF SITEWIDE
Free Shipping
$125
Get Free Shipping when you spend $125+*terms
Discount does NOT apply to Brands We Love items, the Pre-Loved Shop or Gift Cards. This sale may change or end at any date or time. Discount cannot be combined with other discounts. Discount cannot be applied to past or future orders.

USA MADE  •  FEMALE FOUNDED  •  CARBON NEUTRAL

ALMOST THERE! ADD TO UNLOCK FREE SHIPPING!

FASHION

Sashay Vacay: The Cutest Vacation Outfits

Header Image

IN THIS ARTICLE

Whether hitting the road for the ultimate USA road trip, traveling to Hawaii or Mexico for resort life, or even prepping for a European city break - it's time to consider your vacation clothes.

We love vacations and are big believers that a change can be as good as a rest. After the last couple of years, who isn't dreaming of balmy blue skies, swaying palms, chic cities with a thousand spires, or just hitting the open road and heading for sure freedom.

One thing is for sure, travel fashion trends can follow you around the country and beyond and should deffo be a feature when planning your packing. You don't need a full new wardrobe when heading on vacay but a few signature pieces added to your collection can make all the difference.

Those hitting warmer climates need to think about staying comfortable instead of sweaty and with a great mix of daytime casual delights, beach chills, exploring, and sultry nights, we have some clothing suggestions that go beyond the beach and can shake up your vacation wardrobe.

Woven Pants and Halter Top

Woven pants are the ultimate chic comfort wear for whatever vacation you are on. They are comfy enough to wear for exploring especially when paired with a pretty halter top and chunky pair of sandals. They also look great when thrown over a bikini when heading to and from the beach. We love these woven flowy and boho style pants where the high slit invites a breeze to keep you beautifully cool. Pick a bright hot pink halter top or even a cute crop top for a look that is seriously adorable.

Shop all pants and tops

A Bright Floral Dress

Sunshine dresses are one of the best cute vacation outfits. While it's tempting to throw a million vacation dresses into your suitcase, just a couple will do but make sure they hit the mark. A bright floral dress with a flowy feel, strappy shoulders, and a slightly smocked back will not only fit like a dream but it can be worn in multiple ways too. Pair with flats or sneakers and sunglasses for day trips or wear with heels and chic accessories for casual dinners out on the town. Floral dresses are super feminine and finding one that falls in midi style just below the knee will keep you cool and comfortable and sun-protected on your trip.

Shop all dresses

A White Tee and Mini Skirt

Mini skirts never go out of fashion and we love that this once upon a time date night staple has been turned into a must-have item for anyone on vacation. Pick a mini skirt made from the softest fabric with details like tie waist and pockets and with a slightly casual fit and this skirt will serve you well. Keep the sporty cute vibe going by pairing it with a soft white tee tucked in and a pair of white sneakers. This look is an absolute must for exploring a new city in complete comfort.

Shop all tees and skirts

The Dressy Jumpsuit

Don't leave home without adding a gorgeous dressy jumpsuit to your suitcase crammed full of vacation clothes. There's at least going to be one night when you want to get all dressed up for dinner or for a cocktail on the beach. You may also find if you are staying at a resort that resort wear is required for the evening. This jumpsuit ticks all the boxes. Gauzy pink, soft and flowy, and with a wide-legged design, your silhouette will thank you. We love a good jumpsuit because they are always super comfortable to wear without losing an inch of sexy charm. Match this look with fancy footwear like rose gold heels or opt for tan or brown sandals and pick a pretty purse to carry with you. You can also throw on a denim jacket for a more casual vibe or pick a chic blazer or wrap to keep the elegance flowing.

Shop all jumpsuits

The Ruffled-Sleeve Long Tank Dress

A soft ribbed tank that hugs up top and flows from the waist down to the feet is a gorgeous go-to for any destination. We love a long tank in pretty pale pastel hues - especially blue for bringing out the shades of saltwater and sky. The ruffled sleeves, pockets, and rounded hem soften this dress into one of those more casual styles, making it all so simple to dress up or dress down this delight. Simply pair with flip flops or sandals for a casual beach break or opt for wedges or heels for a dressier approach. You can wear a long tank dress for any occasion.

Shop all dresses

The Maxi Dress

No vacation wardrobe is complete without the maxi dress. Women across the world adore the maxi dress for its complete versatility, its utter comfort, and its unflinching ability to look good no matter what. The maxi dress can be worn for practically every occasion under the sun. From beach club babe to city trendsetter, night out, or casual bliss. It's all about how you accessorize - the jewelry and handbags you choose and the shoes you slip on your feet. Pick a maxi with a plunging v neck, strappy shoulders, and even a high legged slit to lend extra sexiness to your summer look. Also, pack a denim jacket or cardigan for those chilly beach breeze eves. When it comes to the magic of a maxi, you can choose a block color in the brightest shades of purple or green, go classic in black and white, or pick a pretty floral pattern or brash geometric stripes - the maxi can handle just about anything.

Shop all dresses

The Slit Maxi Skirt and Sleeved Top

A long skirt is always a stylish addition when it comes to cute vacation outfits. Long skirts are always on trend and are actually super versatile too. You can pair them with crops, tucked in tees, and dressy sleeved tops to suit whatever occasion you are headed for. Pick a maxi skirt in the softest cotton blend and with double slits for an absolute statement look and to bring a slight edge to your feminine appeal. We love this look when paired with a slightly cropped gauzy v neck with button detail down the front and dolman sleeves. Add some wedges or cute heels, grab one of your fave purses, and let this look carry you all night.

Shop all tops and maxi skirts

The Staple Items You Need to Add

Now, we have a few go-to travel outfits picked for every occasion, it's important to remember to pack a few firm staples too. Wardrobe staples are going to save you from overpacking. What makes a travel wardrobe staple? It's an item that can be paired with multiple outfits and turned to time and time again. In short, it's your capsule carry on wardrobe for the road. Take a look at the few staples we have that will save you a ton when it comes to excess baggage fees.

The Black Crop

A good black crop is always a go-to for those who are traveling. It can be paired with just about anything in your wardrobe - from that slit midi skirt to those cute cropped pants. It can be used as a stand-alone top or it can be layered. You can throw it on under a floral dress if you don't want to go with straps only and even tuck in under your jumpsuit. Make no mistake, the black crop is a must.

Shop all crop tops

The White Tee

You need a neutral base in your case when it comes to any kind of trip and the white tee will do just fine. Pick a cozy white tee with a comfortable fit and it will become your best friend for every occasion. Wear it with jean shorts on casual beach days, pair it with loose linen pants, throw it over your bikini, match it with miniskirts, maxi skirts, overalls - a white tee will carry you far.

Shop all tees

The Long Sleeve

Yes, we all dream of endless summer days and sultry nights when it comes to vacations, but sometimes the clouds can come over and the sea breeze can bring a chill. This is where you want a good long-sleeved top to take the edge off. Pick something neutral or soft and simple in monochrome shades of grey or black and white. Throw it on as an added layer over any dress, skirt, or crop combo and stay warm and wonderful no matter what.

Shop all tops

The Pullover

In the same vein as the long sleeve top, all free people understand how awesome it is to sit beside flickering firelight on a beach and listen to the sound of the waves roll in. Of course, for any beachy evening, you need a warm pullover to keep the wind chill at bay. Just because it's a pullover, doesn't mean you need to cut out fashion finesse. We love a pullover with adjustable back ties and puff sleeves for a stunning feminine finish. This is going to look gorgeous slung over jeans, cut-offs, a skirt, and even a maxi dress.

Shop the Arya pullover

The Flirty Skirt

A fun and flirty skirt is a gorgeous go-to when planning your vacation outfits. Pick a mini skirt in a soft and flowy fabric that fits snug at the waist and free flows the rest of the way and you have a show stopper that goes with all kinds of tops and shoes. The flirty skirt is bare-legged beauty and can be paired with sandals and sneakers or crops and shirts, vests and pullovers too. It's also super comfortable for traveling in.

Shop the Paris skirt

The Cut-Offs

Jean cut-offs are a staple for so many casual vacation outfits. Super sexy and super chill at the same time, cut-offs can be worn for all that beach lazing, city-hopping, and when paired with cute boots - you can even wear them for a night out on the town. Who says the cowgirl look is dead? We love cut-offs - dress them up or dress them down with some cute accessories.

The Capri Pants

Cropped pants are another summer must-have. Pick a pair that comes in a muted or neutral tone and it will carry you through your whole vacation. Capri pants that are slightly loose and flowing are super comfortable and can easily transition from day to night just by the simple switch of flats to heels. We are all about capri pants, they look lush with crop tops when high waisted and can also be all Italian elegance when paired with a white linen shirt and oversized sunglasses.

Shop the Tanya bamboo pants

What are your go-to items when packing for vacation? Share all your ideas and fave pieces over at our VIP Sozy Community.

Hello You!

Join our mailing list