Disneyland - Sleeping Beauty Castle

by Jessica Prell

Planning what to wear for a date can be a total nightmare. Now factor in a date that potentially lasts all day and is at the Happiest Place on Earth?! I can’t even.

It needs to be:  comfortable, practical, warm (but also cool in case it GETS warm), appropriate, fashionable, moveable, and above all else…CUTE.

So what do you do? What do you wear?!

Breath. Relax.

Here are 5 tips to dressing for a date at Disneyland:

  • Fleece-lined Tights: Here’s the thing, on most dates you typically want to wear a dress/skirt. It’s cute, it’s functional, and it’s easy. However, the park can be really chilly at night (and in the morning). These babies will be your new best friend. Not only are they insanely comfortable (even the waistband), but they’re fleece-lined making them really warm! Wear them under your dress in the morning and take them off in the afternoon -OR- put them on once the night gets cold. They can easily, and subtly, fit inside your purse. Not wearing a dress/skirt? Wear them under jeans for more warmth- they even look cute under shorts.

    Might I recommend: Urban Outfitters Fleece-lined Tights 

  • A Roomy Bag: You’re going to want a purse with plenty of room! Not only will it still be trendy, but now you have a place to store all the extra things you might need: makeup for touchups, a water bottle, bobby pins, a mirror, a light sweater, and maybe even some fleece-lined tights. No more bulky stuffed pockets, put it all in your purse!

    Might I recommend: Forever 21: Zippered Faux Leather Satchel

  • 0309_Cinderella_Disneyland_March_10_2013Shoes: I want to really urge you to stay away from sneakers. They’re too casual, and usually not date-approapiate. Instead go for a cute ballet flat, boot, or a wedge heel (Sandals can rub or be too cold). Wedges not only are the more stable heels, but they also tend to be the most comfortable heel option. Go for a heel that you KNOW is comfortable and you’re able to walk in. No walking like a newborn giraffe.

    Might I recommend: Faux Suede Strappy Wedges, Loafers (flats), or if you must…these sneakers: Converse

  • Blister Bandages: You wore your cutest pair of shoes, and around hour 4 of park-playing they’re starting to rub….BAD. Now what?! Blister bandages! Pop a few of these bad boys in your purse! You never know when  you may need one. A shoe that is rubbing is one of the worst feelings in the world- so be prepared.

    Might I recommend: Band-Aid Heal Blister Bandages

  • 0283_Snow_White_February_13_2013A Smile: It seems silly that I need to include this in here, but I thought you might want a reminder….remember to smile! Dates can be awkward….and at Disneyland…it might get stressful (long wait times…gross) so relax! Having a date at Disneyland isn’t about all the rides, it’s about getting to spend time together and experiencing Disneyland’s amazing atmosphere. Take it all in. Enjoy. Laugh. The most beautiful thing you can wear is your smile, so remember to bring it!

Now you might say, “But Jessica, you never told me WHAT to wear!” That’s right- I didn’t. Why? Because you should wear something that expresses you and your personality. Jeans? Go for it! A dress? Rock it! A jumper? Awesome! Wear something you feel confident in- just make sure it’s comfortable too. Good luck! You look gorgeous already.

About Jessica Prell:

Jessica Prell - What to Wear: Disneyland Date
Jessica Prell of jessicaprell.com

Jessica Prell loves to help people plan their outfits for dates. When she isn’t helping girls come up with the perfect outfit, she’s writing on her blog (jessicaprell.com), acting, singing, or taking photos of coffee for Instagram (@littleprell). She enjoys boba milk tea, sarcastic hashtags, and a great face mask. It would make her happy if someone other than her Mom followed her on twitter- so please follow her too: @jessicaprell


One response to “What to Wear: Disneyland Date”

  1. Darlene Avatar

    Because of the amount of walking shoes should be supportive first, “cute” second. I’ll bet the male part of this date is wearing them.

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