Started by me, a Los Angeles artist and designer who arrived from Fargo, ND, DAPPER DAY is an organization that celebrates fun, refined style from yesterday and today. We’re best known for producing events that let you “step out in style” at museums, parks, and other destinations.

“I wish I could dress up without everyone looking at me.” That was my motivation behind our first event, an outing to Disneyland. I liked visiting Disney’s parks, they’re rich with attention to detail, color, and exquisite gardens. I also liked clothes, often very colorful clothes, and suits (also usually colorful). And this interest of mine would often draw unwanted attention wherever I went (which was usually by myself). So I needed to find more places where I could blend in with other “dressed up” people–or create those places myself. 

At the time, I was a freelance designer developing theme park attractions, museum exhibits, and other events, and was thinking about how so many of the early concept illustrations of Disney’s parks featured guests who appeared dressed to the nines. Now yes, the 50’s and 60’s was a different time when even a trip to the supermarket might involve gloves and a sharp hat, but it seemed the parks’ designers were aiming to position a visit to these amusement venues as being on par with a night at the opera, or some other haughty cultural affair. And I thought, wouldn’t it be great to bring those illustrations to life, and fill the parks with dapper guests just as the original designers imagined they might be?

I sat on the idea for over a decade, then finally on a trip to Disneyland I was appalled to find my two usually chic friends who were joining me, had donned “tourist drag” for the day to better blend in. Then while waiting for the train in Tomorrowland we encountered a young, smartly dressed young couple who exuded discomfort from how they stood out among the more sartorially lax crowd. I decided I had to do something because there were clearly people like myself who wanted to dress up even as our culture was growing more casual. 

I decided Disneyland should be the site of our first outing, and it would have to be in the winter as it’s more friendly to multiple layers of clothing, (and generally, the more layers, the better the look). So I put out the call and encouraged anyone who wanted to “step out in style” to join me for a day at the park, Sunday, February 20, 2011. I specified “dress up a little–or a lot!” and embrace contemporary fashion as well as vintage styles. The point was for everyone to celebrate their own style. Likewise, by not dictating a strict dress code or period, I hoped guests unaware of the event would notice a difference in how the park looked that day but wouldn't be able to see a clear separation between those participating and those who weren’t. They would just notice the park seemed a bit more special that day. I wanted the boundary to be blurred, I didn’t want to create a dynamic of some people feeling part of a group and others being on the outside.

In addition, I specifically welcomed active and retired service members to join us in their dress uniforms if they liked. Although I’m not from a military family, the issues veterans face has been an ongoing interest of mine. My hope is our events may provide a rare opportunity to wear one’s dress uniform in a non-military setting, increasing visibility, and hopefully engagement, with the wider population. (Also, the uniforms look great.)

About 100 people showed up (including my two friends who’d dressed down on our earlier trip). By design, I wanted everyone to enjoy the park on their own instead of us moving as a giant group. So I only organized one gathering point and that was for an afternoon ride on the Mark Twain Riverboat.

Once word of the event spread in the days after, and photos started to appear on Facebook (Instagram was just a few months old), the idea took on a life of its own. People who missed the event didn’t want to wait a full year to do it again, they wanted to do it the following week! So I hastily announced we’d hold a Fall Outing, Friday September 9th, and added a group evening ride on the Fantasyland carousel. 

About 450 people showed up. I know this because we could count how many times we filled the carousel, and the Mark Twain earlier in the day. The following year, our Spring 2012 Disneyland outing drew about 1,100 people, and our Fall event grew to 4,500. 

At our Spring 2013 Disneyland outing we lost count but estimated 10,000 attendees, plus a reporter from The Los Angeles Times which put the story on their front cover. By now we’d begun organizing outings at the Disney parks in Florida and France too. Between my existing consulting jobs, and these ever-growing events, there was little time to pursue holding events at other venues as I’d always hoped, like botanical gardens, and museums. But we had another problem, we were running out of places that could accommodate the large crowds we were drawing.

Eventually, one season we filled Disneyland to capacity and the park posted notices that if you left they couldn't guarantee you’d be able to get back in. After that event I received a call from Disneyland operations asking me if I know how many people had joined us that day. I said, “It’s your park, you tell me!”

He responded, “Based on our estimates, it appears your event drew between 30,000 and 35,000 additional guests to the parks yesterday.”

The Expo and Beyond

I had always expected these events would be popular, and eventually we could expand to holding an expo and designing fun products and clothes, but this was growing far faster than I ever planned. The first season we made merchandise I wasn’t sure anyone would want our pins, bags, magnets and such, but we sold out in 90 minutes.

September 2014 we launched our first pop-up boutique featuring an assortment of vintage vendors as well as other clothing, cosmetics, and accessories exhibitors at Disney’s Grand Californian Hotel during our Fall park outing. The response was overwhelming, so with Spring 2015 we launched our first DAPPER DAY Expo at the hotel, which continued to expand until we outgrew the space and moved to the larger Disneyland Hotel Exhibit Hall where our Expo continues to happen each spring. 

In 2016 we began our ongoing partnership with LACMA (Los Angeles County Museum of Art) when we held our first event at the museum in celebration of their exhibit, Reigning Men: Fashion in Menswear. Since then we have held events in partnership with the Natural History Museum of Los Angeles County, LA Phil, LA Opera, and others.

As we enter our second decade I have hopes and dreams for all sorts of new ways we can celebrate “fun, refined style.” I’m eager to expand our original designs and accessories lines, and create our own inclusive fashions embracing our whimsical-chic aesthetic. And of course we’ll continue to create events and opportunities for everyone to showcase their personal style, and feel confident expressing it.   


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DAPPER DAY® Events are not associated with Walt Disney Enterprises. Disney properties / Resort photos ©Disney