Maybe you’ve heard of Dapper Day, the unofficial but increasingly popular biannual event in which fashionable people visit a Disney park dressed in their elegant best?
Sounds fun, right? And also maybe a little intimidating if you’ve never done it before.
Southern California’s fall edition of Dapper Day is scheduled for this weekend at Disneyland. If you’ve been thinking about trying out this fashion-forward day of theme park fun, now’s your chance. We asked a group of fashion experts and seasoned Dapper Day attendees for their best tips and advice on everything from putting together the perfect look to how to fully enjoy the day.
Founded in February 2011 by Los Angeles designer Justin J., Dapper Day has evolved into a series of organized outings to Disney parks, museums, and other locales. Though not officially sanctioned by Disney, event coordinators work with the Mouse House to make sure everything runs smoothly.
This weekend’s event, slated for Sunday, Nov. 3, will also feature a Dapper Day Expo on Saturday and Sunday, Nov. 2 and 3, at the Disneyland Hotel. The expo includes a marketplace with more than 75 vintage-style vendors and live entertainment.
If you want to spend more time meticulously planning your Dapper Day look, upcoming events include Dapper Day at Walt Disney World, Nov. 16-17; Dapper Day at the Los Angeles County Museum of Art, Jan. 18; and the Dapper Day spring outing at Disneyland, April 19.
If you’re wondering what to wear, dapperday.com defines “dapper” as “neat and trim in appearance; very spruce and stylish.” The organizers urge participants to “step out in style” and “share your personal flair,” from “vintage classics to chic, contemporary looks.”
Though Dapper Day tends to be associated with vintage-style fashion, organizers say it’s less about period dress than about “sophisticated” and “timeless” attire with an emphasis on personal style. Active and retired military personnel are encouraged to wear dress blues and uniforms. Actual costumes or cosplay are discouraged.
Melanie Cancino was introduced to Dapper Day by people she met on Instagram and customers of her online handmade and vintage accessories shop, Femme De Bloom, which specializes in Disney-themed products.
“It’s certainly grown as an event over the years and it’s been so great to see how people continue to embrace the concept and the events associated,” she said.
When it comes to planning Dapper Day outfits, Cancino tends to base her themes on the season.
“In the spring, I usually wear something floral or pastel and in the fall, I’ll wear darker autumn shades. I have worn a mix of both authentic vintage and vintage reproduction as well.”
Cancino has also put together vintage-inspired Disneybounds for Dapper Day. Coined, created, and popularized by Leslie Kay, Disneybounding involves wearing outfits modeled after favorite Disney characters, attractions, and other theme park elements, but in a subtle, everyday way that might go unnoticed by anyone but especially savvy Disney enthusiasts.
“One of my favorites was fall a couple years ago, when I did an Up balloons-inspired look,” Cancino said.
“Another favorite was when I got to wear this gorgeous mint tulle dress from Unique Vintage for spring Dapper Day two years ago. It made me feel like a princess!”
Two years ago, Cancino brought Femme De Bloom to the Dapper Day Expo as a vendor and that’s been her focus ever since.
“I often don’t get too spend too much time in the parks because I like to be at my booth as much as possible,” she said.
“Being an exhibitor at the expo is such a privilege and I look forward to doing it twice a year. It can sometimes be overwhelming, so the introvert in me often has to mentally prepare for the weekend. It is also a lot of work to prepare for 18 hours of vending, so I’m pretty much MIA the month prior in order to generate enough products for the booth.
“Overall though, it’s a great experience to interact with customers, since I primarily sell online and don’t get to see people face to face. It’s also such an honor to see people incorporating accessories from my shop into their Dapper Day outfits! The expo is a great opportunity to socialize and shop and there’s always entertainment as well, which is fun.”
When I spoke to Harmony Leiker, the Her Universe Fashion Show finalist was in the middle of working on her latest Dapper Day design for Sunday’s Disneyland outing.
“I had a great concept this time around, but ran into some technical difficulties,” she said.
“It’s a bummer, but it happens sometimes. Since I’m running out of time, I decided on a design I’ve had in mind for a while, but never ended up doing. I’m actually really happy with it. Pulling out last minute outfits seems to happen to me all the time.”
On her first Dapper Day outing, Leiker sported a wildly creative yet subtle design based on her favorite Pixar short, Paperman.
“I enjoyed making it so much that I started trying to outdo myself ever year,” she said. “It’s become something of an obsession.”
Since then, she’s designed, created, and worn clever Disneybounds based on Te Ka from Moana, Robin Hood, a mermaid from Peter Pan, and Rainbow Unicorn from Pixar’s Inside Out.
“I like doing more unusual inspirations,” Leiker said. “It’s always fun when someone comes up to you really excited because you’re wearing an obscure character that they love.”
Vintage fashion enthusiast Bre “Sugar” Coe attended her first Dapper Day at Disneyland in spring 2013, after seeing pictures of previous events on Instagram. She joined a Disneybound group on Facebook and learned about “Dapperbounds,” which she describes as “fancy Disneybound outfits.”
This is the style Coe tends to favor for her Dapper Day looks. On her first outing, she wore a Minnie-inspired, 1950s-style red polka dot dress, which landed her on the front page of LA Weekly.
“I made a fascinator of (Minnie’s) original daisy hat and ears to match and wore yellow kitten heels,” she recalled.
In fall 2013, Coe wore a stunning 1950s dress with a flower stamp print, inspired by the “Golden Afternoon” of Disney’s animated Alice in Wonderland. That look was featured in the OC Register.
In fall 2015, she rocked a Mickey-inspired rockabilly ensemble. “All of them were incredibly fun,” she said.
It helps that vintage and rockabilly fashion come second nature to Coe.
“My grandparents were very ‘old school’ and that is a huge influence,” she said.
“Then the vintage style community is just so amazing. Everyone I have met or followed is encouraging, kind, and willing to share tips and tricks. It’s an incredibly welcoming community. If you’re curious about the style at all, there is someone willing to guide you.
“I feel like I fit the target market for (Dapper Day),” she said. “My whole life, I have been drawn to vintage fashion. To me, it’s classy and the silhouettes are flattering. I try to take inspiration from the ‘40s and ‘50s and incorporate it in my look every day.”
It’s no surprise Salazar’s Dapper Day looks tend to be vintage, but they’re also inspired by Disney characters.
“I did a last-minute Belle from Beauty and the Beast look,” she said. “It was a golden-yellow, off-the-shoulder dress with black velvet roses. I was fortunate enough to have my sister, Katie (@styles_bykat), style my hair.
“Another look I often love to do is anything inspired by Agent Carter. It’s nice to have a strong female character that rocks the 1940s style.”
She always dresses up for the event and, this year, intends to push the boundaries of her personal style with her chosen looks.
“I usually opt for a ‘50s inspired look — puffy dress with a fancy hairdo and a hat. This year, however, I’m stepping out of my comfort zone and channeling more of a 1940s-style look with trousers and a turban for one of the days and a wiggle dress for the other day. Both are looks that are way outside of my go-to dress choices.”
If you’re looking for help in navigating your first Dapper Day, here are some tips from the pros:
1. Plan ahead.
It may not be an option, if you’ve just decided to go to this weekend’s Dapper Day at Disneyland, but if you can, give yourself plenty of time to dream up and execute those outfit ideas.
“Be sure not to wait until the last minute to plan or make your outfit,” Salazar said. “I speak from experience.”
Coe advises reserving sit-down meals at your Disney restaurants of choice ahead of time, so you can take a break and dine at your leisure. “You’ll be glad you did,” she said.
She also suggests renting a hotel room, if possible.
“It’s really nice to have a place for some down time/freshen up. Maybe even an outfit change!”
2. You don’t have to go vintage.
“Many feel like Dapper Day is for vintage/retro only but really you don’t have to,” Coe said. “Anything past or present that is stylish is welcome.”
“Due to the 1950s feel of Disneyland, many guests enjoy working mid-century-inspired ensembles for our Dapper Day outings to that park, but this is optional,” the Dapper Day website states.
“We are not trying to recreate a specific period. Just as people once dressed in their Sunday best in the ‘50s and ‘60s when visiting Disneyland, we’re continuing that tradition of ‘stepping out in style’ with a fun contemporary flair.”
3. You don’t have to spend a lot.
If you want to dress to the nines for Dapper Day, you don’t necessarily have to go out and buy something new. You can raid your own closet or check out your local thrift store.
Thrift store stylist Lizzie Twachtman, who owns sustainable online fashion outlet The Thrifty Duckling, is something of an expert in this area. She runs her business from Florida, which is a mecca of cast-off Disney World apparel.
Twachtman attended her first Dapper Day this spring at Walt Disney World and assembled her outfits using thrifted pieces.
“On the first day, I did a Dapper Captain America. I was in the middle of a 30-day series leading up to Avengers: Endgame, all centered around Cap. He’s my favorite Avenger,” she said.
“On Day 2, I did a Dapper Belle from the live-action (Beauty and the Beast) movie. It was a last minute pull-together. But I was so proud of it!”
When it comes to Dapper Day, sustainable, re-wearable looks are a great option, Twachtman said.
“I think thrift stores are the best places to find fun, quirky, lasting pieces for Dapper Day that can then be used in everyday wear afterwards.”
Twachtman suggests two different approaches to searching thrift stores for an ideal Dapper Day look.
“No. 1, decide on a character and then find pieces that you think would work,” she said.
“Try everything on. All sizes, all styles. Consider yourself shopping for the character. It will open up possibilities to find great ideas for pulling off the look.
“No 2, let the thrift store speak to you. Sometimes, when I can’t decide on a character, I let the thrift store decide. I wander through a few rows and see what’s standing out and what it reminds me of. So many times, I’ve found my way to excellent bound ideas.”
You could also turn to The Thrifty Duckling for help. The online shop has a collection dubbed “Disney Bound Boutique,” which features pieces that can be mixed and matched for Dapper Day looks.
4. Be comfortable.
Once you’ve got that perfect look together, it’s time to consider your comfort once you find yourself walking around a theme park all day.
“Whether you’re in the parks or at the expo, it’s a lot of walking and standing, so choose clothing/shoes that are comfortable,” Cancino said.
“I also always bring an extra pair of backup comfy shoes because sometimes I get a little extra and want to make sure I have a photo with a cute pair of heels first.”
“Heels are great for pictures, not so much for walking,” Coe agreed. “Bring something to slip into. I thought I could handle kitten heels. I was so very wrong.”
Coe noted that weather conditions tend to run warm in Anaheim on Dapper Day. “It is always hot, bring a fan. Mandatory. Especially (in the) fall.”
Pro tip: “Adorable” fans are often sold at the Dapper Day Expo, she said.
5. Maximize your photo opps.
Salazar recommends arriving at the park before the crowds and the weather heat up, “while your face is still fresh to snap those photos.”
6. It’s not a competition.
“My advice is to enjoy the day, be present, don’t compare yourself to others, and don’t stress yourself out over wearing the perfect outfit or looking the ‘best,’” Cancino said.
“As the event has gotten bigger, I’ve noticed that some tend to focus on competing or judging others and getting the most attention via social media and that’s just an environment I cannot support.”
“Sure, you can go all out and that can be really fun,” Leiker agreed. “But if that’s not your cup of tea, don’t let it stop you from participating in this awesome event. Wear what makes you happy.”
And don’t be stingy about praising others’ looks.
“If you like someone’s outfit, tell them,” Leiker said. “They probably worked really hard on it and would love to hear a compliment.”
“Many people put a lot of effort into their look,” Salazar agreed. “If you like someone’s outfit, tell them. It’s a great way to meet people and be inspired by others.”
7. Enjoy the atmosphere.
Dapper Day can be a crowded day at the Disney parks, so veteran attendees advised not to expect or attempt to ride all the attractions or do everything.
“It’s a very busy day, so I’d focus on people watching rather than doing a typical Disney day,” Leiker said.
“The Dapper Day hosts really try to make the event as accessible as possible,” Coe added. “Whether you hit the whole weekend or just a few hours, it is the most stunning experience.”
8. Take advantage of the Expo.
Even if you can’t manage going to the parks for Dapper Day this weekend, you can attend the expo at the Disneyland Hotel. And if you are doing the full Dapper Day experience, make sure you don’t miss this part of it.
“My sister and I love to do some shopping at the Dapper Day Expo,” Salazar said.
Chaudhury described the expo as a “very relaxed shopping experience” that’s not limited to vintage wares.
“There is a lot to see but it’s not too huge that you won’t be able to get through it all. Give yourself a few hours to experience it all. There is live entertainment! Each season, there is always a great live band and swing dancing lessons during the show. If you’re so inclined, there is also a cash bar in the expo hall.”
The expo can be a great place to watch the ongoing parade of amazing Dapper Day fashions.
“I love just watching people walk around the show floor when things slow down because it feels like such a fashion show,” Chaudhury said.
“Everyone is so well dressed and some folks even do Dapper-bounds … so it’s fun to figure out which character they are dressed as.”
If you’re still on the fence about whether you want to give Dapper Day a try, everyone I spoke to said it was lots of fun, a day when attendees are on their best, most civil behavior, and an event bathed in the nostalgia of those golden days when Walt still walked the parks.
“Oh, everyone is seriously so nice,” Coe said. “I have never had a better experience at the parks. Picture an old-school movie, people walking along gleefully, where everyone greets each other and pays compliments. If someone accidentally bumps you, they’re so apologetic. It’s like this air comes over the park — a vintage magic.”
Dapper Day requires theme park admission for entry to Disneyland. The Dapper Day Expo runs from noon to 7 p.m. Saturday, Nov. 2, and 10 am to 7 p.m. Sunday, Nov. 3. Admission costs $12.50-$22 ($14 at the door).
For more details about Dapper Day, visit www.dapperday.com. For questions about Disney Parks, see Disney.com. For details about convention-rate hotel rooms and park tickets, contact Disneyland Group Reservations, (714) 520-5005.