How I Styled My Looks for Dapper Day

After my first Dapper Day last year, I couldn't wait for this year to come around so that I could spend another weekend roaming around the Disney Parks in my Sunday best! I got a lot of questions about Dapper Day from family and friends who aren't as involved in the parks culture, about what Dapper Day is and how it works. I won't get too much into detail here about the idea behind Dapper Day, since I talked about that in last years post, and you can find more information on the Dapper Day website. Instead, this year I want to talk a little more about how I prepared my looks for Dapper Day weekend. I'll link items, where I can, incase you're interested in shopping these looks.

Let's begin by looking at the finished product: my looks.

This year, when it came time to plan my Dapper Day outfits, I decided to approach it a little differently. Rather than just coming up with a general vintage Disneybound (like I did last year) I chose to style my bounds around specific style icons. I even made a concept board for reference.

*Note: by no means do you HAVE to Disneybound on Dapper Day. There are plenty of people who just wear a nice outfit that has nothing to do with Disney at all.*

My Saturday look was a Jack Kelly (Newsies) Disneybound inspired by Katharine Hepburn.

With 2019 marking the 20th anniversary of Disney on Broadway, I decided to take the opportunity to pay homage with my Dapper Day look to one of my favorite Disney musicals, Newsies!

(If I'm being totally honest, I chose Jack Kelly as a character specifically because I knew I could use a Santa Fe caption for a picture at Big Thunder Mountain)

Property of Broadwayworld.com

Now that I had an idea of what character I wanted to emulate, I started to think of how I could turn Jack Kelly into a dapper look. After seeing some stunning outfits last year featuring pants, I knew it was something I wanted to do this year. So who better to look to when planning a vintage outfit with pants than the legendary Katharine Hepburn.

Property of Marie Claire Magazine

In the 1940s Katharine Hepburn was not only a star on movie screens across the country, she was also KILLING the fashion game by playing with a more androgynous look- trousers and loose fitting mens shirts. You can see how I chose to represent that with these gray high-waisted paperbag trousers (forever21) and oversized button down shirt (Target). I specifically bought this shirt a few sizes up to achieve Hepburn's more laid back style. I brought Katharine Hepburn's look into my hair and makeup as well with curls and a dark red lip.

For Sunday's Look, I had a slightly different approach.

My original idea was to do a Belle Disneybound inspired by the always iconic Jackie O. This was an idea I've had for a couple of years now, and thought I'd finally be able to realize (There's a whole story here that I'll write about at a later time because I just can't get into it right now). Unfortunately, that plan fell apart exactly one week before Dapper Day.

Luckily, I found this gorgeous dress in my closet that my mom had given me for Christmas. The first time I wore it was to a friend's wedding, and my sister had said I looked like I belonged in The Marvelous Mrs. Maisel.

Property of The Marvelous Mrs. Maisel on Amazon Prime

As I looked at this dress and tried to figure out how I could "disneyfi" it, I thought about how the dark blue with the light blue flowers reminded me of a garden at night- then it hit me.

A Dapper 1960s outfit inspired by my favorite scene from the live action Cinderella.

Because this was a very subtle and abstract Disneybound (if you can even call it that), I really used my accessories to tell the Cinderella story. The gold purse was from The Disney Store's collection for the live action Cinderella a few years back (no longer available). My bangle is from Lillian & Co., and features lyrics from the song A Dream is a Wish Your Heart Makes. Finally, since I didn't have a pair of glass slippers on hand (and since my feet were dead from walking up and down Main Street in heels the day before), I wore a pair of Toms (no longer available, except on ebay), featuring Cinderella's favorite helpers, Jack and Gus.

So that's it. This was the thought process that went into creating my Dapper Day 2019 looks. Please remember that this was just my personal process. There are literally no rules that say you must DisneyBound or you must style your outfit based on any particular person.

I'd love to hear about your Dapper Day look, and how you put it together! Leave a comment below with your process, or any Dapper Day ideas you have for the fall!

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See ya real soon!
Sarah