As a Disney social media geek, Dapper Day has been on my radar for a few years, but the timing was never great, and I really didn’t know anyone as dorky as me who would dress up for a few days in the parks. I mean, the amount of times I have friends and acquaintances say “I don’t know HOW you wear dresses to Disney World!!” Um, simple, y’all. It’s like wearing ventilated PJs in 100% humidity. How do you NOT? 😉 But I digress.
Enter my boss turned bestie, Constance. Girl goes dapper on a daily basis aaaaand she was a budding Disney adult just looking for someone to show her the ropes. A match made on Main Street! Knowing the more the magical…er, hello to firecracker Scarlet who is a ride or die and always up for anything. Armed with our Amazon Prime accounts, three Cricuts and two heat presses, we accepted the challenge.
Without further ado, our fabulous five tips for Dapper Day at Walt Disney World!
1. Everything’s Better with Friends
Whether you bring your own or hit it off with other dappers in the parks, this day is the most fun when you get social!! Follow the hashtags, take pictures with other guests and don’t forget to wish everyone a “Happy Dapper Day!” I was lucky enough to bring two of my best girls, but you if you’re the only one who can get the weekend off, hang out on the Dapper Day Facebook group while you’re prepping for the big event and connect with fellow park dwelling fashionistas and fashionistos.
We found these amazing little dapper dolls outside Tower of Terror, and they excitedly wished us a “Happy Dapper Day” and posed for pictures like true pros. We also met tons of other guests and found new Facebook groups, instagram friends and TikTok buddies!
And if YOU want some ready to roll Dapper social friends…
2. Pick a Theme, Any Theme
While anything fashionable (of any era) goes for Dapper Day, we had so much fun planning around a theme. And, honestly, it kept us reigned in a bit. Although we changed our minds no less than 87 times in the approaching weeks prior to Dapper Day, knowing our theme helped us focus on what colors, pieces and accessories we’d need.
We ended up centering around our favorite attractions. We all opted for Haunted Mansion on day one, then Constance and I repped Tower of Terror on day two while Scarlet preferred its shorter, less threatening neighbor, Lightning McQueen’s Racing Academy. Not really her favorite attraction, but she fell in love with the look.
3. Get Comfy & Creative
Don’t get me wrong. Some guests are all in, and I applaud them for it, but heels in the parks are no for me, dawg. I’m a hefty gal, and I like some surface area when I’m walking all day. I am a champion for heels in a purse for photo ops, though, and I may just do that this spring (a la my Capture Your Moment looks).
Consider fabrics when you’re swiping through your closet or Unique Vintage. It’s Florida. It can get real sweaty, y’all. You can totally work that vintage polyester number, but I loved my breathable cotton dress in the post-rain humidity.
Don’t be afraid to get creative with your outfits! Looking for the perfect outfit can get a little pricy or even impossible, especially if you end up looking for pieces as niche as Disney Parks themed. Several items in our wardrobe were very simple picks from Amazon that just needed a little creative license taken to them. Thank you Cricut and Siser!
4. Focus on Photos
We always take a ton of photos on vacations, especially Disney vacations. But Dapper Day is different. It’s basically a living, breathing photo shoot, so be sure you’re camera ready!
- Keep a portable charger for your phone with you or pack a wall charger and juice up during meals.
- Buy Memory Maker. Bonus, if you’re going with friends, you can split the cost! Pre-purchase for the best deal.
- Book an actual photo shoot. The groups are chock full of photogs, or you can opt for a Capture Your Moment session from Disney PhotoPass.
- Don’t forget everyone else! I really wish we’d gotten more photos with other guests. The pure genius of some of these looks were worth a snap or two at least!
5. Do You, Boo!
In truth, it can get a little…intimidating in the Facebook groups, especially for first timers, but remember, the purpose of Dapper Day is “for everyone to celebrate their own style.” Don’t worry about not dressing up enough. Or too much. Or in the “wrong era.” Or…or…or.
Just do you! No matter your attire, you’re part of the crew, and you will be welcomed and complimented and have the most magical time! And if you see us, be sure to say hey and get ready to strike a pose!
Bonus Tip: Put Your Best Face Forward
Remember that Florida humidity? It can rain havoc on ya girl’s already slick face, but my make-up stayed perfectly put with Urban Decay All Nighter Setting Spray and Eyeshadow Primer Potion. And although I’m a Sephora girl at heart, my favorite for lips is Maybelline Super Stay 24 Liquid Lipstick! Some of these and the links below are affiliate links, and we’ll (hopefully!) get a small commission if you purchase through them.
Ready for the Pictures?!
I told you it was a veritable photo shoot!
Haunted Mansion Looks
Hollywood Studios Looks
And an Extra Credit Disney Bound
Being that we’re all educators, we couldn’t pass up the chance for extra credit (and an extra mental health day!).
Extra Credit Tips
Enjoy the attractions
Grab a drink
Get matching tats
Take a break
On second thought, maybe just matching bracelets...
Shop Our Looks
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Constance
Skirt – Obbue Dresstore
Top – Romwe
Shoes – Dream Pairs
Ears – Her Universe
Jess
Dress – The Dress Shop Haunted Mansion Ballroom Ghosts (retired)
Shoes – Torrid
Sunnies – Unique Vintage
Bag – Dooney & Bourke Haunted Mansion Crossbody
Constance
Dress – Shein
Vest – Design by Olivia
Shoes – Dream Pairs
Ears – CL Gift
Jess
Dress – Nemidor
Shoes – Torrid
Flower Clip – Cellot
Belt – Grace Karin
Jess
Skirt – Unique Vintage
Top – Unique Vintage
Shoes – Rothy’s
Belt – Grace Karin
Scarlet
Top – Shein
Shorts – Shein
Suspenders – Chiyu-yang
Shoes – Converse
Now Go Get Dapper!
Hopefully these tips helped hype you up for your first Dapper Day, but if you have any questions, let us know in the comments. We’ll be happy to answer everything we can and find answers for the questions we can’t. Happy Dapper Day!