Why the Midi Skirt Is the Ultimate Vacation Staple

As you may know, I recently went on vacation to Maui. And it was perfect. We had the most beautiful weather, the sun was shining every single day, and it was sooo relaxing. And don’t worry, I haven’t forgot about the travel guide I promised in this post – stay tuned! For now, I’m going to talk about why the midi skirt is the ultimate vacation staple.


When it comes to packing for any vaycay longer than a week, I can get a little, let’s say, overindulgent. But I know I’m not alone – You never know what you’re going to want to wear, if there might be a weird and unlikely weather system that sweeps the area, or exactly what you’ll be doing on your vacation. It definitely helps to plan out some things before your trip so it’s easier to pack, but some things will also be spontaneous!

For this particular trip I knew there would be lots of beach time, strolling and exploring, and a few fancy dinners and happy hours. We made most of our meals in our hotel room since the Canadian dollar is so low right now, but had to make it out to some of our favourite restaurants such as Cheeseburger in Paradise and Kimo’s!

There are so many reasons why midi skirts are the ultimate vacation staple. They’re comfortable, breezy, and go with anything from a high-neck fitted tank like I’m wearing here, to a crop top or bralette, to a loose, tucked-in tee.


I found this pleated midi at J. Crew (on sale, heck ya!). I don’t see it online anymore, so I’m guessing it’s sold out. But who knows, there may be some floating around in stores still. It came in this pretty soft pink colour, as well as a navy blue, and I thought this one was perfect as we head into summer – and of course, for my Maui vacation!

I paired it with the Free Label Trail Tank, which I’m OBSESSED with. Seriously, it’s perfect. I bought it with the intention of wearing it to yoga, as it’s nice and lightweight, but soon realized it makes an amazing everyday piece, and with the high neck, can even dress an outfit up!

All of Free Label’s products are made with renewable and eco-friendly resources like bamboo and organic cotton, and they’re made locally in Toronto and Vancouver! The line was started by two of my AMAZING friends who are devoted to ethical and sustainable fashion. I have all three of their tops and I pretty much live in them! They’re awesome basics.


The tanked worked perfectly tucked into my midi skirt, and I accessorized with this beautiful light brown leather purse my boyfriend’s parents brought back for me from Italy, these strappy black sandals from Aldo (last year, similar here), and this Daniel Wellington watchwhich has become a daily staple.

This was one of our final nights in Maui and we shuttled into the town of Lahaina. We did the happy hour at Kimo’s and ordered way too much food, and spent the night walking around the charming town, popping into stores and enjoying the beautiful views.

Midi skirts allow you to feel comfortable as you’re walking around, and although they’re almost floor-length, they still allow your legs to breathe, so you can wear them in hot weather. Plus, they make dressing up so easy! All you have to do is slip on a midi skirt and it can bring your outfit from casual to chic in a cinch! And when you’re on vacation, what could be better than that?


The last thing you want to be doing is wasting time picking an outfit when you could be exploring and enjoying a new (or loved) place! Pieces such as the midi skirt make vacationing so much easier because you don’t really have to think about it. You’ll look put together with hardly any effort, and will be able to get out and enjoy your time!

What do you guys think of the midi skirt? Do you agree with me, or do you have another favourite vacation staple? let me know in the comments section below!

And don’t forget to share this post with your friends on Pinterest!

If you’re going on vacation, a midi skirt is the perfect piece to bring with you, whether you want to dress up your outfit or keep it casual. This pleated midi skirt was my go-to on my beach vacation, and in this post I show you exactly how to wear a midi skirt and let you in on why it’s the ultimate vacation staple! Click to read it now or save this pin for later.

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