The Best Way to Plan & Pack Summer Vacation Outfits

In this style guide, I will be talking about chic summer vacation outfits as I start packing for Greece. It seems so long since we went on vacation! I’ll show you the pieces that I think are essential to pack and, of course, all the outfit ideas I’m planning.

What to wear on the plane to vacation

Plane outfit

First things first, I have to think about what I’m going to wear on the plane. I decided to go for this beautiful, Parisian blush pink top and cardigan set with a pair of jeans.

Transition set with a vest and cardigan

This is a great transition set where you can wear just the vest and pop the cardigan on when the weather gets colder.

Flattering bikini in deep blue


Around the pool, I’ll be wearing this bikini which looks flattering on me, and I love the deep blue tone. 

Black swimsuit with details

I tend to take three or four bikinis or swimsuits with me on holiday. This is one of the others I’ll be taking, and I love the detail on it. 


When thinking about those chic summer vacation outfits, I try to think about the pieces I’ve got in my wardrobe that I can mix and match in two, ideally even three different ways.

How to put together vacation outfits

1. Long skirt

Here I’m wearing a long skirt and a vest top with a shirt over it. This is a really nice hot weather outfit, perhaps for early evening. It’s super chilled and laid-back, just how I like it.

All those individual pieces can be mixed and matched with other items I’m taking. So I’ll wear the vest top with a pair of shorts and the skirt with a different blouse top.

If a piece is going in my case, it’s got to be worthwhile. 

Denim shorts with a floaty top

2. Denim shorts

In this outfit, I’m wearing some denim cutoff shorts and have paired them with a lovely floral blouse.

I adore the shape of this blouse; it’s very floaty and light, so perfect for the heat. I also think that it feels quite elevated and dressed up, so I can imagine making it work for the evening as well.

Another great thing to bear in mind as you’re packing your suitcase is: is it only going to tick a box for the daytime, or could you possibly make it work for the evening too?

If it does both, you know you’re onto a winner - it’s going to double up very easily.

Casual vacation outfits

3. Light pants

When packing pants, my top tip is that if you have two pairs in a similar color, only take one of them. I'm packing a pair of cream linen ones, as they’re light and breathable in the heat, as well as a navy pair. I'm also packing some camel-toned pants.

Here, I’ve styled a pair of camel pants with a silk blouse in a similar color. I love the tones together, and the different textures give the look a bit more depth. Pairing the outfit with my sandals keeps it very low-key and casual.

Summer dress in khaki

4. Summer dresses

Here I have a mini shirtdress in khaki that I’ve styled with a tan leather belt.

Beach vacation outfit ideas

This dress will also double up nicely as a cover-up. You can open up all the buttons and just wear it loose as if it’s a boyfriend shirt.

This will give me a bit of coverage by the poolside. As a happy bonus, I think the tone works lovely against the navy bikini as well.

White maxi-length summer dress

One dress I love taking away with me to somewhere hot and sunny is this white dress made from 100% linen. It’s just that perfect summer dress that you can throw on top of your swimsuit or bikini and go for lunch in, and you feel like you’ve made an effort.

Black maxi-length summer dress

Here is the same dress in black, which again is great to wear in the heat because it’s very breathable. I find the pinafore shape really flattering, and as the dresses don’t take up a huge amount of space in my suitcase, I might get away with taking both.

Navy and beige maxi-length summer dres

Here, I’m wearing a navy and beige check dress. Instead of wearing it with sandals, I’ve put it with my ballet flats that are in a very similar tone to the beige of the dress.

I think it would look equally as nice with tan details, so I could take the sash belt off and add my tan belt and a pair of tan leather sandals.

Straw bag for the pool or beach

5. Bags

In terms of bags, I’ll be taking my straw bag as I’ll wear that every day when heading down to the pool.

Tote bag for the plane

On the plane, I’ll take my tote bag. Taking a big bag means I’ll be able to put some toiletries in here, my makeup bag, and a couple of books.

Smaller purse for the evening

For evenings, I’ll take this bag with the gold chain. I think I can make this work with pretty much everything I’ve taken to wear in the evenings for dinner, so it has to come with me.

Strappy sandals for vacation outfits

6. Shoes

For shoes, I’ll be taking these brown strappy sandals, as well as a pair of gold ones. 

Brown slip-on shoes

I have these brown slips-ons which are nice and easy.

Ballet flats to wear on the plane

And I’m going to wear my ballet flats on the plane.

Summer vacation outfits

There we have my summer vacation outfit ideas. The most important thing is to pack versatile individual pieces that you’ll be able to style in a few different ways; that way, you’ll get the most out of the clothes you’re bringing.

Now I’m all packed and ready to go!

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