I’ve always admired Dapper Days at the Disney parks from afar. But when my planned spring vacation overlapped with the Disney World Dapper Day 2021 event, I knew it was a sign. So this year, instead of watching recaps from my couch – I dove straight in.

Held two or three times a year, Dapper Days are a celebration of all things vintage fashion. Ranging from inspired Disneybound dappers to immaculately tailored 3 piece suits, fashionable fans will travel from around the country to sport their Sunday best inside the parks. Both Disneyland and Disney World celebrate their own seasonal Dapper Day gatherings and people watching at the park on event days is truly something special.

This spring, I had a chance to chat with fantastic folks participating in Disney World’s Dapper Day 2021 to discuss their inspiration, vintage fashion, and the dapper community.

@AFROLECTRIC @TALK2THEPALM

@THELADYTROOPER @THETROOPERDUDE

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While I expected to be impressed with the fashion – I was even more blown away by the passion and warmth of the Dapper community. Even with my Amazon pillbox hat and definitely not vintage dress, I was welcomed to the celebration. Every person I connected with shared how truly happy they were to be a part of the community – self-expression via fashion is just one small facet in why so many choose to participate in the event.

The next Dapper Day gathering is scheduled for Disneyland on November 14th, 2021. My vintage newbie self can’t wait to join in on the all fabulous fun. Find more information on upcoming events at dapperday.com.