How to Dress to Impress: Dapper Day at Disneyland

by | Nov 7, 2022 | Disneyland, Disneyland Parks, DLR News, News Outside the Parks

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Find out how to participate in DAPPER DAY at Disneyland and what happens during the annual DAPPER DAY Expo in Anaheim, California.

If you’re like me, any day at Disneyland is cause for celebration, but DAPPER DAY takes the idea of spending a special day at the Happiest Place on Earth and gives it the ultimate stylish spin. If you long to express your personal style with other sartorially-minded folks, this might just be the event you’re looking for.

What is DAPPER DAY?

Blue Dresses for sale at the Dapper Day Expo

Photo by Danny Shuster

Founded in 2011 by Justin Jorgenson, DAPPER DAY has quite an origin story – and now over a decade later it’s become a well-known event in America and Europe, especially for Disney fans who attend the DAPPER DAY Disney Park outings in Anaheim, Orlando, and Paris.

Fantasyland all over print button-down shirt

Photo by Danny Shuster

It’s an excuse to dress up in your Sunday best, take photos with your friends, and enjoy the attractions in the parks. I adore the photos of Disneyland’s early days with families all done up for the special occasion of visiting the park and recreating that feeling during DAPPER DAY has been a way for me to scratch that nostalgic itch, as well as to experience a new way of embracing my Disney fandom (yes I admit, you’re more likely to see me in athleisure wear than a sophisticated sundress during most of my visits—but that’s what makes DAPPER DAY so much fun!).

What is the DAPPER DAY Expo?

Mannequins wearing some rather dapper outfits at the Dapper Day Expo

Photo by Danny Shuster

In addition to DAPPER DAY events throughout the year (not all of them happen at Disney parks, by the way!), they hold two expos a year (in the spring and fall) at the Disneyland Hotel, and this weekend, we were invited to attend.

It’s the biggest style celebration in California, and we chatted with guests who ran the gamut from massive Disney fans to those who were there purely for the excellent array of vintage-inspired fashions. Dozens of vendors filled a 30,000-square-foot ballroom at the Disneyland Hotel convention center, and this was the absolute best shopping experience I’ve ever had.

Decorative umbrella

Photo by Danny Shuster

Clothing booths had everything from beautifully preserved vintage pieces to brand-new items that celebrate classic fashion. Styles for women (including maternity items!), men, and children were available, and with Christmas around the corner, I was delighted to find lots of holiday-season attire available!

Shoes, hats, fascinators, scarves, and jewelry were all available too – I even found some pieces to enhance my look for the weekend and instantly upgraded my ensemble. There were also some booths dedicated to Disney fandom accessories like pins, stickers, and artwork inspired by Disney characters, lands, and parks. Makeup and hair artists were available to style you up.

Exclusive pins from the Dapper Day Expo

Photo by Danny Shuster

And—totally unexpected, but kind of perfect—there were even classic cars and vintage motorcycles on display and a tattoo artist who was inking people right on the premises!

A major highlight for me was the performance by the L.A. Swing Dance Posse—these cool cats showed off some of their best moves on the dance floor with numbers like “shake, rattle and roll” and “chew tobacco.”

LA Swing Dance Posse at the Dapper Day Expo

Photo by Danny Shuster

I loved the energy of their performance and the diversity of their dancers who all came together through their love of swing! They even helped the crowd out with a lesson on some basic swing moves so everyone could cut a rug this weekend.

A collection of vintage (and very dapper) sandals and shoes

Photo by Danny Shuster

Tickets are available for one day, or the whole weekend at dapperday.com.

What is DAPPER DAY at Disneyland?

A pair of Dapper Day attendees are wearing their Cinderella and Prince charming Disneybound outfits, looking at the camera and smiling

Courtesy of Kyra Wellborn, by Erick Paul Photo

DAPPER DAY hosts outings to various Disney parks, and this weekend there was one at Disneyland, on Sunday only (though the expo ran both Saturday and Sunday). During the outing, attendees mingle with regular park guests during normal operating hours and turn heads with their elevated attire. This portion of the event isn’t ticketed through DAPPER DAY, though you do need valid park admission and a park reservation.

To avoid crowding, most of the festivities simply include running into other attendees and striking up a conversation (everyone is friendly, easy to spot, and eager to talk about their sophisticated style).

This weekend, an optional mid-afternoon meetup to ride the Mark Twain and an evening meetup to ride King Arthur Carousel as a group was organized.

Several of the local social clubs like Main Street Socialite organize their own in-park meetups to take group photos throughout the day too. You can participate as much or little as you like, and that includes just admiring outfits as a spectator if you’re not ready to take the leap of dressing up for your park visit!

What to Wear to DAPPER DAY

I found this to be the most stressful part of the DAPPER DAY experience, but now that I’ve been I assure you there is nothing to worry about. At both the expo and the outing, outfits ranged from full-on glam with ball gowns, crinolines, high heels, fur stoles, and sky-high updos to simple a-line skirts or slacks, nicely fitted tees or cardigans, white tennis shoes, and accent “D” brooch.

Everyone looked fabulous and there was no shaming if your outfit was on the less dressy end of the spectrum. While many attendees plussed their outfits by making them Dapper AND Disney-inspired, the Disney angle is not a prerequisite for this event.

Check out DAPPER DAY on Instagram for some inspiration or follow along #dapperday on any social media channel to see what others are wearing to the event or have worn in the past.

The outfits can be effective whether elaborate and hand-made or simply picked up at The Dress Shop in Downtown Disney or Disney Springs. Many attendees I spoke with had borrowed items to perfect their look from other fashionistas and in general, there was enthusiasm among guests for dressing up to any degree.

WDW Magazine Creative Director Danny Shuster, dressed up for the Dapper Day Expo

Photo by Danny Shuster

On Saturday to attend the expo, our Creative Director, Danny, and I donned vintage-inspired outfits influenced by Adventureland. He wore khakis and a straw fedora, paired with a green Tommy Bahama aloha wear shirt, green socks for a pop of color, and the last-minute addition of a fresh orchid which was a garnish from our breakfast at Tangaroa Terrace.

WDW Magazine CEO Stephanie Shuster posing outside the entrance to the Dapper Day Expo

Photo by Danny Shuster

I wore a beige, orange, green, and black butterfly dress, black flats, a colorful bow, and a jade elephant necklace to tie the look to Danny’s. I used pops of color in my makeup and found a 2-minute hair tutorial that helped bring a little more style to my look. We were both pretty comfy – a nice benefit for those not used to dressing to the nines each day!

WDW Magazine Creative Director Danny Shuster, dressed up for Day 2 of the Dapper Day Expo

Photo by Danny Shuster

On Sunday we were a little bit more formal in Cinderella-influenced blues – me in a blue and white tea-length dress with a “D” logo belt and glitzy jewelry, and Danny in grey slacks, a blue blazer, a grey linen pork pie hat, a patterned shirt and an Imagineering pin from Mickey’s of Glendale at the 2022 D23 Expo.

WDW Magazine CEO Stephanie Shuster, dressed up for Day 2 of the Dapper Day Expo

Photo by Danny Shuster

We purposefully chose shoes we could wear with both outfits that were comfortable enough to wear for several hours. We didn’t feel out of place on either day and had lots of lovely compliments on our outfits! 

If you’re worried like I was, head to the expo on your first day – you’re sure to find something perfect to wear. Or, shop on the DAPPER DAY store online before the event!

Upcoming DAPPER DAY Events

DAPPER DAY outings to Disney parks happen throughout the year, and usually you can partake in their group hotel rates for some great savings! Here’s a list of upcoming events:

  • December 10-11, 2022: WDW FL Holiday Outings
  • April 15-16, 2023: DAPPER DAY Expo at the Disneyland Hotel (Spring Outing to Disneyland CA on April 16)
  • April 29-30, 2023: WDW FL Spring Outings
  • May 13, 2023: Spring Outing to Disneyland Paris
  • November 11-12, 2023: DAPPER DAY Expo at the Disneyland Hotel (Fall Outing to Disneyland CA on April 16)

Is DAPPER DAY Worth It?

That’s a big YES from me! If you like to dress your best every day, enjoy feeling fancy every now and then, and are looking for a unique date or girl’s trip, DAPPER DAY is the perfect excuse to indulge in your sartorial leanings.

The outings are good fun, and the expo is really something to behold, especially if you love fashions from different eras. I can’t wait to attend my next DAPPER DAY—hope to see you there!

Written by Stephanie Shuster

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A lifelong Disney fan with a passion for globetrotting, I’m driven by a desire to build a community where people like me can let their Disney flag fly with pride. As CEO and Owner of WDW Magazine, I lead a team that connects thousands of Disney fans to the Most Magical Place on Earth from wherever they are.
Stephanie Shuster

Written by Stephanie Shuster

A lifelong Disney fan with a passion for globetrotting, I’m driven by a desire to build a community where people like me can let their Disney flag fly with pride. As CEO and Owner of WDW Magazine, I lead a team that connects thousands of Disney fans to the Most Magical Place on Earth from wherever they are.