What the Disney Style Editors Would Wear to Dapper Day

Attending Dapper Day requires so much careful planning and anticipation, I’m always kind of bummed when the day is over. Luckily for me this year, just a few weeks after Dapper Day at Walt Disney World is this season’s Dapper Day at Disneyland! Thank goodness for short waits.

All of the Disney Style staff is obviously already planning their Dapper Day outfits. I love how everyone’s looks show off their unique personalities–what era they decide to channel, which Disney films, characters, or designs they incorporate into their looks. Take a look at what we’ve got planning, and can’t wait to see you at the Park!

Prince Naveen


“I’ve never been to Dapper Day, but as a Disney fan ready for any excuse to dress up, I know it’d be my kind of thing. Inspired by the charming (and abundantly dapper) Prince Naveen from The Princess and the Frog, I started from the bottom up, choosing a pair of two-toned Oxford flats that looked both character appropriate and perfect for racing between rides. I switched out his button up and trousers for a delicate blouse and skirt, adding a sweater vest for extra retro flair. I also threw in Naveen’s ukulele for good measure— not because I can play the ukulele, nor because I think it’d be easy to tote around, but because I refuse to pass up the photo-op at Café Orleans. #DoItForTheInsta” – Iman

Skirt: Lisa Marie Fernandez, Top: Miguelina, Hat: Eugenia Kim, Backpack: Chanel, Lipstick: Sephora Minnie Collection, Phone Case: Zazzle, Shoes: Miu Miu


Amelia Dapper Day Style

“My Dapper Day outfit is definitely more Tomboy-style than the usual Dapper Day attire seen around the Parks. To me, Dapper Day is more about having stylish fun with your outfit than anything else, which is why I chose a colorful printed top and sailor-inspired shorts in a bright color. As for shoes and accessories, I went with comfortable oxfords perfect for walking around in, retro sunnies, and a cute wicker bag in the shape of a fish.” – Amelia

Play Gulf Shorts in Red from ModCloth, Shelly’s London ‘Emma’ Platform Oxford in White from Nordstrom, Quay Australia ‘Avalon,’ Retro Sunglasses from Nordstrom , Wicker Fish Shoulder Bag from Talbots , Toucan Play This Game Top from ModCloth

Contemporary and Cute

Ilana Dapper day Outfit

“As the Dapper Day website says, “‘Dapper’ doesn’t mean just vintage!” For me, Dapper Day is all about embracing personal style, having fun, and staying comfortable. I chose an A-line silhouette that alludes to vintage fashion, while still being trendy and contemporary. While I wish I could join the ambitious women who wear heels for the day, the closest I can go without being my clumsy self are flat platforms like these. Finally, my Dapper Day look wouldn’t be complete without a Snow White bold red lip color, which matches my accessories!” – Ilana

Skirt: Lisa Marie Fernandez, Top: Miguelina, Hat: Eugenia Kim, Backpack: Chanel, Lipstick: Sephora Minnie Collection, Phone Case: Zazzle, Shoes: Miu Miu

Audrey Hepburn

Shelby Dapper Day Outfit

“My all-time favorite (non-Disney) movie is Sabrina, staring Audrey Hepburn. If I could design and wear my ultimate Dapper Day outfit, I would base it on one of the looks she wears in the film when they go boating, combined with another look she wears when she arrives home from cooking school (I’ve seen this movie like 500 times, obviously). It’s a very summery mix of high-waisted shorts, a wrapped blouse, espadrilles, big hoop earrings, and a turban, which you can really only pull off at Dapper Day. I’d add in some favorite Disney pins to show off my Disney love, as well.” – Shelby

Floral and Girly

Taylor's Dapper Day Look

“It wouldn’t be a true Dapper Day for me without two things – floral prints and feminine accessories. My love for all things girly is real, so this daisy romper is everything paired with simple flats, a yellow hair bow, and dainty jewelry. I wasn’t sure at first about mixing brown and black for the purse, but as our fellow editor Ilana would say, there are no rules in fashion as long as you feel good!” – Taylor

Romper: Kate Spade, Bow: Bowtique London, Phone Case: Sonix, Earrings: Missoma, Purse: Tory Burch, Watch: Kate Spade, Shoes: Chloé, Ring: Bing Bang

Posted 4 years Ago
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