Winters Past

20th Century Fashion from Deco to Disco

Dressing Vintage for Dapper Days

The modern era is a casual time. CEOs of major corporations wear jeans and hoodies to work. The lines between athletic attire, sleepwear and everyday clothing have blurred.

And yet, people still crave a reason to get dressed up.

I have quite a few customers who dress head to toe  in fancy vintage clothes and go to Disney parks for a big festival two times a year.

The gathering is called Dapper Days and it looks something like this:

 Dapper Days

Wearing their vintage finest to Dapper Days

When Disney Land opened in 1955, people wore their best outfits to go there. Now people wear tee shirts, flip flops and baggy cargo shorts. Where has the sense of pageantry gone?

People who ask themselves that question have developed loosely organized club. They come up with a modern riff on the party clothes of previous decades. Often their outfits allude to the fifties, when the theme parks were new. They meet up with other like minded folks and, from what I hear, they have a blast.

It’s a very creative project for them and they have so much fun with it every step of the way.

It’s also a bonding thing between friends, couples, and families. 

Here are a few of my customers in their Dapper Day best:

Dapper Days

A mom & her daughters

Dapper Days


Ray and Joanie are a couple who fully embrace creative self expression in their clothing. I’ve written about them beforeThis is what they have to say about Dapper Days:

“Dapper Day was originally founded at Disneyland in California as a day where people would dress up like Mr. and Mrs. Disney would have dressed in the 1950s. It has evolved into a weekend where people put on their best vintage attire and enjoy looking stylish.

We do our best to dress in accurate vintage attire, using as many original pieces as possible to complete our outfits. Joanie sews most of her clothes, sometimes using vintage patterns, but all of her accessories are vintage and picked to enhance the period authenticity of her outfits. Ray prides himself in finding vintage suits and hats and adds vintage accessories if possible to complete his outfits.

We use old movies from the 1930’s, ’40s and ’50s as reference for our clothing.”

Joanie has a nice collection of vintage hats, purses, gloves, jewelry , some of which she inherited from her mother and grandmother. She and Ray noticed that some other Dapper Day participants also wear inherited pieces, bringing a very sweet dimension of family history to their  event.

 Dapper Days

Ray and Joanie at Dapper Days

Like Ray and Joanie, many Dapper Days participants strive to remain authentic to their chosen era. Others add elements of fantasy or costume to a vintage silhouette.

There are, of course, layers of nuance that come into play when one strives for authenticity.

When Mr. Disney created mini world with pretend castles and a faux main street 45 years ago, did he imagine that it would become a very real part of people’s lives?

Like the Velveteen Rabbit, does a created environment become real when filled with the genuine love of actual people over time?

Author: Winters Past

I am a vintage clothing shop owner living and working in rural north Florida. I believe in adding a little vinegar and molasses to my greens, having my coffee outside whenever possible, and mixing something vintage into every room and every outfit.

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