Adorable Family Outfit Inspiration for DAPPER DAY at the Parks


image source: jessica mcdonald | katherine rose | disney family

If you’re a Disney fan, you may be familiar with themed days at the Disney Parks. One that definitely stands out is the fan-run event DAPPER DAY! It happens twice a year at Walt Disney World and Disneyland Resort, and everyone comes to the Parks dressed to the nines in vintage-inspired outfits.

My family and I love to dress up, so having an excuse to be in our Sunday best at our favorite place on earth (Disneyland) is all we need to have a fun-filled day! We not only go to Disneyland dressed up for DAPPER DAY, but we also like to DisneyBound. This term was coined by Leslie Kay that refers to dressing in outfits inspired by Disney characters. Here are my favorite DAPPER DAY DisneyBounds to inspire your family outfits.

Lady and the Tramp

Last fall, we decided to do corresponding family DisneyBounds based on my favorite film: Lady and the Tramp. I was Lady, my husband was Tramp, and my 2-year-old was the iconic spaghetti! We pulled from the colors of the characters, and finished off with a scarf and bow tie inspired by the dog collars.

image source: katherine rose

When brainstorming ideas, I recommend that your littlest one is an icon from the movie for the added cuteness factor — like we did with our daughter’s gingham tablecloth-inspired dress and spaghetti headband. 

image source: jessica mcdonald


Last DAPPER DAY, we dressed as Hercules, Megara, and Pegasus! I love to pick characters you don’t typically see at the Parks. Hercules DisneyBounding is sure to grab the attention of Disney fans, especially those who were ’90s kids!

image source: katherine rose

For Hercules, try incorporating an icon like a thunderbolt or cloud. For Megara, a shawl was the perfect way to incorporate a Grecian style. For Pegasus, finding a headband or necklace with feathers or wings makes for a nice, subtle touch. With characters that have such bold looks, color blocking can also make your inspiration very recognizable.

image source: katherine rose

Peter Pan

This DAPPER DAY, we decided to take a more villainous approach with a few of our outfits! I am DisneyBounding as Captain Hook, my husband is my sidekick Smee, and my daughter is Tinker Bell. 

image source: jessica mcdonald

When planning your outfits, adding icons or objects help accessorize and identify the character. I added a feather in my hair for Captain Hook, my husband donned an anchor-shaped tie clip for Smee, and my toddler wore little wings for Tink. It’s the subtle accessories that really make a look dapper and unique! Patterns also help — if you’re able to find one similar to the character, like this striped jacket to represent Smee’s striped shirt, your looks are sure to make their mark.

image source: jessica mcdonald

From putting together outfits with your family to enjoying a day at the Parks with other DAPPER DAY fans, it’s a wonderfully unique way to bond as a family at the happiest place on earth. Enjoy the fun-filled event at Disneyland Resort November 4-5 or at Walt Disney World November 18-19.

For more magic, check out this Chewie Chews & Blue Milk recipe:

Posted 3 years Ago
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