How To Plan Cute Vacation Outfits You’ll Actually Wear

It’s vacation time, baby! Planning outfits for a vacation can be overwhelming if you don’t go on vacation a lot. I personally only have work-from-home outfits and lounge basics, not ‘vacation outfits’.

Vacation outfits really depend on your personal style. Do you like dresses over skirts? Do you wear denim shorts or flowy, loose pants? Are you all about casual looks or do you dress up on vacation? Are you going to be active on your vacation or is it a rest and reset vibe? 

I’ll give you the basic ideas of a bunch of different vacation outfit ideas for you to give your own personal spin on them. I also have some fun stores where to purchase vacation outfits and my personal favs to shop!

Vacation Outfits Pieces

  • Flowy Pants or Flowy Skirts
  • Matching Sets
  • Kimonos
  • Boujee Night Out Outfit
  • Unique Swimsuits

Stores To Shop At

If you are looking for the typical, floral, bold colors, different-than-your-regular-everyday clothes, these are the stores I would shop at.

Flowy Skirt or Pants

Flowy anything at the beach just feel right! The sun setting with your hair (and pants) flowing in the wind and the smell of the ocean. Picture perfect!

flowy pant outfit ideas

Whenever you have something loose on the bottom, you usually always want to have something tight on top. There are some exceptions but that’s for another day.

Shop my fav flowy pants and skirts:

You might be asking, what would I wear with flowy pants or a flowy skirt? Here is a perfect pairing:

  • Swimsuit (bikini top or one-piece)
  • Crop top – You could do a puffy sleeve or tight little cropped tank top
  • Bodysuit
  • Graphic T tied at the waist
  • Bralette – same idea as wearing a bikini top

Matching Sets

Who doesn’t love a matching set? It’s the next best thing if you don’t like rompers or jumpsuits. You have three outfit options in one.

matching set for vacation

Wear it together or wear each piece separately. And when you are short on time, you know what top to wear with your bottom for a fast outfit option.

Shop my favorite sets:

Kimonos

Kimonos are so versatile, you should pack one (or two) for every trip.

swimsuit coverup

They can be worn as a swimsuit cover-up, over denim shorts with a shirt, or some of them can be worn on their own as a dress if they are designed that way.

vacation outfits
You can’t really tell but I am wearing a kimono here. It’s just blowing in the wind. Also, I’m 19 weeks pregnant in the pic.

Shop my kimono picks:

Night Out Outfit

Always have AT LEAST one dressy outfit when on a vacation. Even if you plan on laying by the pool and ordering room service every day.

You. Never. Know!

dressy outfit ideas

This could be a little black dress, a long flowy white dress, a skin-tight jumpsuit, or a bright fun cocktail dress. This one is definitely up to your personal style what you will bring.

You can always dress them down with a denim jacket if you don’t end up needing a fancy look. Check out this blog post with denim jacket options and how to style them!

Shop my fav dressy dresses:

Unique Swimsuits

I’m all about standing out when it comes to swimsuits. I love something that is different and makes people ask where it’s from.

I’m not into the thong bottoms personally but you do you!

vacation swimsuit

You can never go wrong with a classic black one-piece or bikini but switch it up, you are on vacation.

Shop my swim picks:

Vacation Outfits Inspiration

flowy pants outfit
flowy pants oytfit summer
flowy skirt outfit beach
kimono vacation outfits
kimono over dress outfit

Would you wear these on vacation? Let me know your vacation outfits must-haves!

XO, Annie