14 Flirty Plus-Size Vacation Outfits

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14 Flirty Plus-Size Vacation Outfits

Are you planning a vacation right now? If so, we want an invite! One of the most exciting things we love about vacation time is packing a fun and flirty travel wardrobe. Not only do you want to relax on vacation, but you also want to look and feel your best. Besides, we believe that the quickest way to total relaxation is through a great outfit that hugs every curve right. 

Are you planning a tropical getaway somewhere warm where you will need flowy dresses and flattering bikinis? Or are you heading somewhere north where it’s chilly and you’ll be spending your days cozied up next to a fire? Either way, each kind of vacation sounds so good right now … and we have the perfect outfits in mind for both occasions. 

If you’re looking for vacation outfit inspiration, we’ve got you covered! As you start to pack, keep this style advice top of mind so that you can plan unforgettable vacation outfits that are spicy and instagram-worthy. And what’s more? We’ve brought a little extra heat to this style guide by including outfits that are fun and flirtatious. So, if you’re hoping for a little vacation romance—whether you’re going with your boyfriend or hoping to turn heads while lying on the beach, these outfits will do the trick!

There are so many places we’d love to go on vacation, so we made sure that our style guide is broken down by the type of vacation you will be going on. This ensures that you pack the best outfits that are right for the season and climate—and we even included some style advice for the flight there and back. Because even if you like to keep it comfy and cozy on your flight, the first outfit sets the tone for the rest of your vacation. So, let’s get packing!

no apologies dress mustard

Outfits to Wear on an Airplane

How are you getting to your destination? Whether it’s by train, plane or car, we want you to look stylish while you’re en route. No matter what method of transportation you’re taking, all of these outfits were made to cross borders! This first look marks the beginning of your vacation, so while it’s important to get into a relaxed and comfortable state of mind, we also want your confidence to level up, too. So, here are our favorite outfits to travel in. 


We don’t blame you for wanting to keep it comfortable on your flight or car ride to your destination. So, if you're looking for an outfit that still is very chic and polished while also being as comfortable as pajamas, let’s try an athleisure look. The athleisure style is one of our favorite trends because it combines comfort with impeccable style. Pair your favorite gym or sweatsuit set with a cute pair of fashion sneakers and top the look off with a statement duster coat or a moto jacket. You are going to look like a star in this outfit! 

Pairing your favorite gym set, especially if it’s a sweatsuit, with a chic coat will give you a major street-style vibe without even trying. We love traveling in layers because you never know if you’re going to be hot or cold. It’s always best to come prepared so that you can remove or add layers as needed. 


No surprise here! Leggings are the perfect bottoms to wear on a flight, on the train or while driving. They’re so comfortable, and they’re very versatile. So, even if you wanted to go for a more dressed-up look, you can easily top your leggings off with a chic cardigan and one of your favorite blouses. 

Sweater Dresses

Traveling to or from somewhere cold, but still want to look like the fashionista you are? If so, we suggest wearing your favorite sweater dress. You can easily top this look off with a duster coat, which will elevate the style. Or you can just wear it as-is with a cute handbag or your luggage in tow. If you don’t like the idea of wearing a dress while traveling but still want to feel dressed up, throw on some biker shorts underneath your sweater dress for an outfit that practically feels like pajamas but looks as good as a night out.

beachy dress

Beachy Dress

If you’re ready to just be on the beach already and you don’t mind getting dressed up for a flight, dress for your destination! If that’s a tropical beach, then why not wear a dress you’re really excited about wearing in the tropics. We love a really flowy and loose maxi or midi dresses for a flight. And if you really want to give everyone travel envy, top off this outfit with your favorite floppy hat. Everyone will know exactly where you’re heading. 

Warm Weather Vacation Outfits

Are you heading to the tropics or somewhere with beachy vibes and warm weather? If so, we are extremely jealous. But we want you to look so good on vacation that everyone will be turning their heads. So, without further ado, here are our favorite flirty outfits to wear on a tropical vacation. 

Flowy Dress

If you’re planning to relax while also looking fashionable, might we suggest a flowy maxi dress? Whether you sport a floral-print or a bright color, this dress will be your go-to on vacation. It’s easy to throw over any kind of swimsuit before you walk the beach at night. These dresses are made with your curves in mind so you’ll instantly look sexy while also appearing very confident.

coastal craze swimsuit

Sexy Swimsuits

If you’ll be by the pool or beach, you definitely need plus size bathing suits that hug every curve just right. These swimsuits should make you feel confident and beautiful. So, whether you love a one-piece, a bikini or a tankini, wear what you feel your most confident in. 

And if you’re feeling a little anxious about wearing a swimsuit, spend some time learning about the body positivity movement. You deserve to rock and feel great in a swimsuit because your body is perfect just the way it is. Learning more about the body positivity movement will show you that other women have overcome their worries and fears of wearing a bikini in public, and it will make you feel empowered!

A Bodycon

Are you planning a night out while on vacation? If so, you absolutely need a curve-hugging dress that highlights your best assets. When you look good, you feel good. And we know that you will feel your best self in our plus size party dresses. From sparkles to lace, and other curve-contouring dresses, you’ll find everything you need for an unforgettable night out.

Swim Cover-Up

It’s great to have a swim cover-up on hand, whether it’s a flowy dress or a crochet tunic, because you never know what the day will bring! Pack a cute cover-up in your suitcase and in your backpack so that you’re ready to go from the airport to the beach to dinner and then to wherever the night takes you.


Packing jumpsuits for a tropical vacation is a must for us! Sometimes, we need a break from the chub rub that one incurs during a beach getaway. Jumpsuits are very flattering and they’re fashion-forward. So, no matter what you’re doing, you’re sure to look like a bombshell. And what's better? You’ll give your thighs a little bit of love and a little bit of a break from rubbing together. 

rompers vacation outfit


if you’re not feeling a jumpsuit and you also don’t want to wear a dress, rompers are the perfect in between—and they look absolutely adorable on you! At Chic Soul, we love rompers because they make the perfect vacation outfit. Top your romper look off with a pair of heels and some dainty jewelry for a fun and flirty outfit. Look at you, turning heads!

Cold Weather Vacation Outfits

If your idea of a relaxing vacation is somewhere in the mountains skiing or building a snowman, you’re going to love these winter vacation styling tips. We love the idea of escaping it all by staying cozy and cooped up in a cabin—whether you bring friends or it’s a solo trip. But what do you wear for a week on the slopes? We have the perfect outfits in mind that will keep you cozy while also looking cute. 

Lounge Pants

If you plan on spending a lot of your time inside, pack a cozy pair of plus size lounge pants or loungewear sets that aren’t sweatpants or leggings. We want this loungewear set to feel special because you’re on vacation and you should feel stylish even if you’re just lounging. Like we said, we want you to feel like your best self during this relaxing time. 

If you’re looking to make your loungewear look more luxurious, we love monochromatic loungewear sets. This color scheme instantly elevates any look—even if you’re wearing joggers and a hoodie. Lounge dresses and loungewear sets with bold prints and patterns are also a fun way to keep your spirits high during vacation. Choose one or two different loungewear sets that match the vibes you want to create during your winter vacation.

angel in you sweater


If you plan on heading outside during your winter getaway, packing leggings is a great idea. Leggings are super comfortable and they can be layered if you need additional warmth. They also pair well with virtually any kind of sweater and outerwear. Whether you’re sipping hot cocoa on the patio or going out to a lodge for dinner and drinks, leggings will be your best friend. And what’s more about leggings? They’re very flattering and curve-hugging. Top off your leggings with knee-high boots or some cute snow boots to dress them up a little bit.


Jeans are a great piece of clothing to bring on a winter getaway because they’re on the thicker side and they are more durable. We prefer denim with a little bit of stretch so that you can live in them all day. Pair them with a cute sweater and any kind of outerwear you may need. This look is simple but it’s chic. If you’re going for a flirty or sexy look, try an off-the-shoulder sweater. Showing a little bit of skin during your winter getaway will be a huge confidence boost. 

Sweater Dresses

Just because you’re going somewhere cold, doesn’t mean that you have to abandon dresses altogether. Besides, what’s vacation without a fun and flirty dress? We recommend styling a long-sleeve sweater dress with a pair of tights and some cute booties. This is a winter outfit we love because it hugs all of your curves in the right places and it’s super cozy.

styling sweater dresses

Now, let’s get to packing! We don’t blame you if you have a million outfit ideas after reading this style guide. As you fill up your suitcase with your favorite outfits, you may be wondering if you should take the more practical approach and pack only the things you wear often. Or, if you should take a risk on this vacation and pack that dress that’s still hanging up in your closet with the tags on. 

While we want you to be as comfortable as possible, this is also a great time to take risks with your style—but you can always pack backup clothes in case. And don’t worry if you overpack. It’s better to be over-prepared than to be underdressed! We hope you have the best vacation ever. And we know one thing is for sure! You are going to be looking stylish as ever.