What Stylish Women Actually Wear on Vacation

A quick scroll through Instagram is enough to give you major wanderlust—jet-setting "it" girls and frequent flyers constantly make us long for a holiday in a far-flung paradise. But once the time for a vacation finally arrives, we make panicked purchases, thinking we definitely need another bathing suit, chandelier earrings, and a bucket bag. Instead, why not build your resort wardrobe over time and take the stress out of packing altogether?

To help us figure out how to craft the perfect holiday wardrobe, I tapped the best people for the task: stylish Instagram "It" girls who travel a lot. Curious to know what they pack in their suitcases? I found out for you and you'll never want to go on vacation without these chic finds again.

Dressing for the pool when you're staying at a luxury resort (or perhaps on-board a cruise ship) takes a little more thought than putting together an outfit for the beach, but it needn't be difficult. After all, fashion should always be fun! 

No one wants to walk up to the poolside in denim shorts and flip-flops only to find that every other person is in a kaftan and heels, so we've put together a helpful dressing guide to make sure that when you turn heads at the poolside, it's for the right reason. Here's what to pack when you're headed on holiday to a luxury poolside location.


Poolside lounging at a luxury resort is as much about being seen as it is about relaxing and soaking up the sun. Don't just settle for a standard triangle bikini - this is your opportunity to really show off your sense of style by picking swimwear that makes a statement!

Think glamour and luxury - if it wouldn't look out of place on the pages of Vogue, it won't look out of place here. Certain resorts may have dress code rules, so it's probably best to avoid offensive slogans or anything too revealing, like a thong bikini.

Most people go to the resort swimming pool just to sunbathe or dip their feet in the edge, so take this as the perfect opportunity to buy that beautiful-but-impractical swimwear you've been lusting after. Whether that's an off-shoulder swimsuit or a crochet bikini, who cares if you can't actually swim in it easily?

Flattering One-Pieces

Cover up the glamorous way

It's generally good resort etiquette to cover up when you move away from the pool and surrounding sun-loungers, to order a strawberry daquiri from the nearby bar or head back to your room. 

Forget shorts and a tee though. At a luxury resort, a stylish cover up or beach kaftan is practically a must-have! Show off your tanned legs in a hip-length version, or up the wow factor with a full-length one. If you're looking for a bit more coverage, for example to take you straight from poolside to brunch at the resort restaurant, pack eye-catching day wear pieces such as dresses and loose trousers that look laid-back but not too casual. 


It's all in the accessories

Don't neglect the finishing touches - the right ones can elevate your outfit from "that's pretty" to "wow, I simply must know where she shops!". In fact, accessories are probably the biggest difference between dressing for the beach and for a luxury resort - no one in their right mind would wear stilettos on the sand, but don't be surprised if you see a few people at the resort wearing a pair!

Aim to pick accessories that make a statement all on their own - a giant hat for example - but are still cohesive with your overall look. For example, nothing says luxury like a flash of gold, but if you're choosing a gold necklace or gold bracelet, be sure to stick to complementary colors and overall, make a cohesive look with your jewelry. Luxury resorts are the perfect place to show off those big, statement pieces like necklaces and earrings, but for a look that's more subtle pack this delicate body chain, to add a touch of extravagance to your bikini or plunge-necked swimsuit.

If money is not a problem, I can suggest a Cartier bracelet (s). I see them often on jet setters during their beach vacations.


Of course, sunnies are a must and the more stylish the better. 

Straw Hats

 Finding the perfect straw hat—one that's both stylish and durable—is no easy feat.  Nanushka hat.

The All White Outfit

Just like the LBD (little black dress) is a year round must-have, so is the all white dress. The all white dress is a staple in your closet, especially around the winter to springtime transition. Whether you’re going on a cruise, lounging at an all inclusive hotel somewhere warm and tropical or if you’re going somewhere else exotic and full of sunshine, all white is mandatory. Short white dresses in the bodycon silhouette, whether short or long sleeved, are always a fresh, bright look for women and girls of any age. White lace dresses are a timeless, classic look that keep you looking delicate and feminine. It’s a new year and a clean slate, rock white to represent a new beginning.

All-white can be not only a dress but a romper, shorts and tops, etc.

Solid Color Bright Sundresses or Romper

Anything that’s light and breezy is a must for vacation wear if you’re headed to a warm, sunny destination. Pack away your dark colors to make way for lighter, brighter colors and prints. Swap those dark burgundies and go bold with a red, pink  or yellow dress - all perfect colors for a sunny brunch date in the caribbean or a stroll along the beach in the Polynesian Islands.

Floral Sundress or Evening Dress

The floral trend isn’t anything new. Spring after spring new floral prints arrive for our spring and summer wardrobe and year after year…we all eat it up. What is it about floral print that every girl loves? It’s hard to know.

I think part of the reason we love floral is because of how versatile it is. Florals can make you feel sweet and feminine, but you can also style them to be edgy and tough. You can get a large floral print, small floral print, mix-match florals, or just a floral accent. The possibilities are truly endless. Not to mention, there is just something about floral prints that is happy. And, when you wear florals you immediately feel happier because of it.

Floral 2 Piece

Stylish Solid Color Maxi Dresses

Many of us rely on a lot on neutrals in our wardrobe while at work, but vacation time is great time to use bold colors.

Stylish Jumpsuits

Light Chiffon Dresses 

Silk Dresses

I see a lot of bloggers wearing silk dresses at resorts during their vacation.

Dinner or Special Event

In my opinion, for special event like wedding on the beach or dinner you could wear all white or a long silk dress.


If there’s one designer shoe you invest for your vacation in warm places, make it the Hermes Oran sandals. The sleek style that you’ll find in nearly every fashion blogger’s closet since at least 2016 and is available in many color-ways, the most popular being tan, red and black. You’re sure to get your money's worth as you can wear the leather sandals with literally any summer look. Hermes simple slides come with huge price tag, so there is a budget option: buy Steve Madden Greece sandals that almost look identical for $60 or find other rip-offs that will cost you even less: $40-$50.

Here are Hermes sandals and Steve Madden rip-offs. While Hermes Oran look slightly better and might be a better quality, you still get quite a close version of the same sandals in Steve Madden's style.


How to wear sandals in summer:


To say that the straw bag is having a moment is an understatement. It’s everywhere: circle cross body bags, oversized beach totes, bucket straw bags, arc bags, etc. The original trend statement began with the Cult Gaia Arc bag a couple of seasons ago and that just opened the flood gates. It quickly became the “It Bag” of style bloggers, celebrities and everyone in between. It goes with everything and it super cute! It’s an investment as well because I don’t see these bags going out of style any time soon. Cult Gaia Arc Babboo bag retails $170 but there are different cheaper dupes of it available for about $40. Same goes for circle cross body bags. You can buy them for around $30. I saw great ones on Etsy.com shipped from Bali.


Expensive Looking Colors for Your Holiday

See my blogs about "How to look expensive" but in short, these are pastels, white and natural colors. 

Not Classy

Obviously, we all have different taste, but skip the outfits below if are going on vacation to an expensive resort. The girl below looks like vacationing in South of France. It is not a good look for a vacation there.