How to Dress Cute and Comfortable in a Theme Park: Molly’s Tried and True Picks

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Hey howdy hey everyone! Molly here!

Me with my cookie twin. (It’s glittery and full of coffee.)

Recently, I’ve been writing a column from time to time answering your questions. Things like “The Makeup That WON’T Melt Off Your Face in Disney World.” For this post, I’ll be answering more of your questions — but on one much-requested topic: THEME PARK FASHION.

I don’t consider myself a fashion influencer AT ALL, but I do enjoy being comfortable and cute in the Disney and Universal theme parks! If you enjoy that too — then keep reading. I’ll be sharing my tried and true favorite brands of shoes, lipstick, and my secret weapon for wearing skirts without chafing. (I gave up shorts long ago and never looked back.)

Molly’s Tried and True Theme Park Fashions

What do you mean you wear skirts?! How do you not have chafing issues?

First things first: my theme park fashion is essentially just a cool Disney/Universal t-shirt and then a bottom. It used to be shorts (usually denim), but chafing is literally the easiest way to ruin my day at Disney World. There was one day at Universal’s reopening that I almost cried I was so uncomfortable — despite using Megababe anti-chafing rescue (which I still love and recommend).

Is this TMI? Sorry, not sorry, I am here to save your vacation.

Hogwarts in a Skirt

I vowed that very day to ditch the shorts and live my life in skirts and dresses. How you may be asking? How are skirts possibly better than shorts?

SLIPSHORTS. That’s how.

Slip shorts can take you to infinity and beyond.

If you’re unfamiliar, slipshorts are undershorts that are meant to be worn under skirts and dresses. I have tried quite a few pairs but my favorite is this Jockey collab from Target. They are very thin so they don’t make me hotter in the already hot Florida sun, they don’t ride up, and they come in various lengths. I literally have 10 pairs.

I do still carry Megababe with me as an emergency backup (and it helps other places than thighs) but I am not kidding when I say I have worn these slipshorts for 14 hours in a theme park on a very regular basis. Since wearing them full time I have not once had a chafing issue. They will CHANGE YOUR LIFE. You’re welcome, ladies.

Get my tried and true Slipshorts here!

Where do you buy said skirts?

Most of my clothing comes from the exclusive Targé Boutique (Target) and ASOS! I usually stick with denim cause they typically have pockets.

Here are a few of my favorites that are still available:

Skirts and coffee what more could I need?

Black Classic Denim: Asos

Soarin’ with Style.

Front Seamed Denim: Target


Blue Button Down: Asos

Nothing beats new ears and a cute skirt.

I also find denim A-line to be the most flattering cut on me, which is why I tend to stick with those!

What kind of shoes do you wear for all-day walking?

If there is one item of clothing that needs to be comfortable at Disney, it’s your shoes. I walk anywhere from 14,000 to 20,000 steps on an average day, so I need shoes that can literally go the distance.

I wear sneakers 90% of the time. I’m not particularly loyal to any one brand, though I mostly own Nikes.

Betty Boop!

My go-to style is called the Tanjun (which is Japanese for simple) because they are…simple. I have three pairs! They’re super lightweight and comfortable — both of which are very important for walking all day.

Shop the Nike Tanjun here!


Superstars and Santa Goof! (Photo from 2019)

I also own a few pairs of Adidas Superstars. While very cute, I don’t find these QUITE as comfortable in the toe area for a super long day. But a normal length day these do okay!!

Shop the Adidas Superstars here!

No matter what shoes you decide on, make sure you break them in BEFORE you arrive at Disney. Practice walking in them — honestly up to five miles a day — so you’re ready for a theme park!

What kind of lipstick do you wear that stays on all day?

While no lipstick I’ve tried stays on perfectly all day, a few of my favorites do a pretty dang good job.

Thank GOODNESS for Fun Lipstick Colors!

One I really enjoy is this Maybelline Super Stay Matte. It stays on pretty well (even under a mask!) and it’s also the lipstick that has survived days at Typhoon Lagoon and Castaway Cay.

I also like that it’s $9, because I can buy lots of colors without guilt.

Grab the Maybelline Super Stay Matte here!


My favorite superhero in a fancy suit.

My other go-to is Lipsense. It’s kinda a pain because you need a gloss and a color to make it work, and it’s one of those MLM products you have to find a distributor to buy from. Also, it’s $25 a color (not counting the gloss).

But all that said, OMG does it work. It easily stays on all day, through many drinks and treats. And it also stays on very well under the mask — but sometimes needs touch-ups because the gloss doesn’t hold up quite as well as a matte.

I’ve tried to stop buying Lipsense because my bank account hates me, but I keep coming back.

For a full peek inside my makeup bag, check out this post!


Where do you get your Disney and Universal shirts?

Like I said earlier, the easiest way for me to make a cute theme park outfit is to pair a cute themed t-shirt with one of my many skirts.

I buy most of them at Target, the parks themselves (or on shopDisney or Universal’s online shop), and occasionally Amazon. Another great under-the-radar spot is Uni-qlo, the Japanese department store in Disney Springs. I’ve also gotten some very cute ones from Disney Food Blog’s Teespring shop.

Pro-tip: I often buy kid’s t-shirts in the biggest sizes possible. They’re cheaper and they have cute styles!

Here are links to a few of the most-requested ones that are still for sale!

MORE tye-dye.

Gray Minnie T-Shirt: Target

Kid’s T-shirts rule.

Disney TWO PACK Tees: Amazon

I loveeee this one.

Princess Kindness Tee: Target

Glitz and Glitter

Tower of Terror Glitz and Glitter: Disney Food Blog Shop

Greetings from Hogwarts

Harry Potter Tee: Box Lunch

Basically, tuck a cute t-shirt into a cute denim skirt (or tie it up) and you’ll immediately look put-together in my book.

What do you wear for rain?

You DO have to prepare for rain in Florida, even when it says there’s no chance of rain. That’s a lie. There is always a chance of rain.

It’s called fashion, look it up.

This is my go-to rain jacket. It folds up pretty small so I can shove it in my backpack, and it’s thin so it doesn’t make me too hot! Plus I love the olive green and pin-stripes in the sleeves and hood. And it’s a great price!

Shop my rain jacket here!


I also bring a pair of water-proof Target sandals with me when it looks like rain. My particular pair isn’t available anymore, but they could come back! They are knock-offs of these Birkenstocks, which I have only heard great things about.


Shop the waterproof Birkenstock Arizonas here!


So there you have it: my tried and true favorite brands and products for being cute AND comfortable in the theme parks! Thank you for sending in your questions — I hope this was helpful when you’re gearing up for your next park trip! If just one person discovers the beauty and magic of slipshorts, I’ll consider this article a success.

The makeup that won’t melt off your face in Disney World!


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Molly is a lifelong Disney enthusiast, and former Walt Disney World Guest Relations Cast Member and tour guide. Her Walt Disney World favorites include Festival of the Lion King, Big Thunder Mountain Railroad, Fantasmic!, Mickey-shaped pretzels and rice krispie treats, and anything with Buzz Lightyear! She lives in Orlando with her husband (who she met in Guest Relations) and their two rescue dogs, Kronk and Cruella de Vil (Ella for short!)

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30 Replies to “How to Dress Cute and Comfortable in a Theme Park: Molly’s Tried and True Picks”

  1. Thanks Molly! Going to use those tips!
    I would like to add to the shoe list. Vessi is an online brand from here in Canada. They are comfortable and waterproof (great for Florida rain). My daughter wears them every day in her dog walking job. I got a pair for Mother’s Day and will be wearing them for our August trip.

  2. Do you wear the slip shorts in the dead of summer? We are coming back in September and wanna make sure I get some if you don’t get too hot!

    1. Hi Jess! Molly says the slip shorts are thin and made of a breathable material so she wears them all year round.

  3. Molly, I love these articles for myself, but I could also use one on your husband’s preference for long park days. My husband already has chaffing issues on a regular day, and I’m curious if their are any particular fabrics he prefers or any products you know of that are a lifesaver for him as well.

  4. Hey Molly. Thank you so much for all the tips. Going to all parks at the end of November to celebrate Birthday and 18 years with my better half. Keep doing a fantastic job you and the crew are truly appreciated. ❤️From NYC

  5. Thank you so much! I just found your YouTube channel and I love the videos esp with my trip coming up this Feb. I did notice in your videos you wear super cute facemasks. May I ask where you buy yours?

  6. Last trip, I wore dresses many of the days, and I chose to wear some very thin bike shorts under them that had pockets. Even if the dress didn’t have a pocket, I was always able to keep my phone (which also has my wallet) close at hand. It was the best experience I’ve had. I’ll be wearing many more skirts and dresses this summer, that’s for sure!

    1. Brilliant! I have lots of pocket bike shorts I wear at home & under dresses, but I never thought of using the pockets when I’m wearing a dress. I’ll definitely have to try it!

  7. For those who prefer capris or longer pants, look into Eddie Bauer’s First Ascent line. The Guide Pro pants and capris are lightweight, with handy sleek side pockets perfect for phones. Lots of nice colors. I live in them. They have occasional sales, which is the time to grab ’em 🙂

  8. I have given up shorts long ago for skirts at Disney. Most important is to find them with pockets and made from lightweight fabric. Molly is right. You won’t regret it.

  9. I am planning my first trip in about 9 years. We are coming in December. Do you have a recommended long pant/leggings for comfort? I love your style and even though I’m much older I like to look cute and want to be comfortable.

  10. I am one who suffers horribly from heat rashes on my legs. Made the mistake a few years back wearing jeans at Disneyland….we will be in wdw in May. Not gonna make that mistake again. I’m gonna go for some wicking Capri flare leg yoga pants. And I have a ton of Disney shirts from Torrid one of which being Grogu!! But I’m curious where you get your sunglasses from. They always look amazing!! Please share!!

  11. Agree with skirts and dresses. My favourite day in the park was when I wore a dress. I did it because I didn’t want the usual shirts outfit at Cinderella’s royal table. It was the best day, so comfortable and easy to get in and out of rides. I also did the ‘shirts’ underneath.

  12. I am plus size and also LOVE the Jockey slip shorts. I prefer wearing cotton sundresses or skirts with them. Otherwise, I wear the longer bermuda style shorts (jeans or twill) to prevent chafing. My favorite tennis shoes for the parks are Adidas Ultra boost. Like Molly, I bring a pair of basic flip flops for water rides, then switch back to tennis shoes.

  13. I wouldn’t recommend Birkenstock’s for the parks unless they are a very well worn pair.

    First, Birkenstocks are not truly broken in until the excruciating pain drives you to weep and tears fall from your face onto the sandals. Seriously, I birks need to be worn one full season before they are ready for something like this.

    Second, the cork sole in birks doesn’t do well in the rain. They get super gross after they get wet and the leather can pull out of the cork.

    The style of them is good though. I’d just recommend a good pair of rubbery waterproof ones instead.

    1. Birkenstock now has a line of rubbery sandals! I have ha pair of the Gizas that are entirely that material. I jokingly call them my “Birkencrocs.”

  14. Thanks Molly! This was so helpful! Love the maybelline super stay lipstick! I spray urban decay all nighter setting spray over my makeup for extra hold even through splash mountain rides! I wear the Tatiana denim skirt from just black it’s super stretchy unlike some denim and has pockets. I wear Nike reacts for sneakers. I get my favorite tees from target, box lunch, shopDisney, and cakeworthy! I use deodorant or baby powder for chafing but will try your recommendations!

  15. From, your videos you said your Aunt makes a lot of your masks? What fabric does she use- they look so light and comfy- I make my own and would love to know what kind of material she uses!

  16. I love wearing Teva sandals for days in the park!! Most of them are already waterproof and have a back to them so can’t fall off on rides and are very comfortable while still letting your feet breathe!

  17. Another great suggestion for a bottom. Lululemon tennis skorts. They have the non slip shorts and even have pockets! My go to now every time!

  18. I am trying those slip shorts out STAT!!! We are planning to go back in August and I think I will be wearing my comfy sun dresses to the parks (the fam will be so happy I’m not forcing them to wear matching shirts this trip!). I use body glide, but I am so trying those slip shorts!

  19. Oh wow this is AWESOME!!!! We are going in March and I am trying to pull together comfort and cute so perfect timing! I love the simplicity and the fun vibe. I love that you include comfort tips because nothing can fix being uncomfortable all day.. lipstick tips as well! Plus we forgot rain gear plans – and that jacket is a must get. All your tips are great but this was a treat and I appreciate you! We need to post our Molly inspired ensembles under #allearsmollystyle. Let’s just make that a thing. Cheers!