Dapper Day at the Disneyland Resort is just a few days away! For those of you who don’t know about Dapper Day, it is the day that you can get really dressed up (usually in vintage style clothing) and go to Disneyland in style! It is amazingly fun to watch what everyone else comes up with for their outfit, and to dress up for a day of fun.
If you’d like to participate in Dapper Day events, you can get complete details here.
For this post, I’ll be breaking down some of my favorite outfits from past Dapper Days, and giving some recommendations on where to start for creating a Dapper Day outfit of your very own!
Everyone gets dressed up for Dapper Day! That’s my mom wearing a Lucille Ball-inspired outfit, and Haley Martin rocking her preppy ensemble with a peacoat jacket.
1. Pick an Era or Look.
The foundation for every outfit should be the era or particular styled look that you are trying for. You can pick a decade of fashion, or try something more specific, like 1940s pinup, to set the parameters for your outfit. Here are some ideas to get you started:
- 1940s Pinup
- 1920s flapper
- 1950s Housewife
- 1960s Mad Men style
- 1970s Disco
- 1930s Old Hollywood
- 1940s Andrews Sister/World War II chic
From there, I recommend starting a board on Pinterest to collect your thoughts. You can find some vintage makeup tutorials, advertising images from the era, and great outfit inspiration on Pinterest. From there, you’ll have a much more solid base when searching for the components of your outfit.
My Andrews Sisters-inspired outfit from Dapper Day. I paired a military style jacket with a hat that I got at a military surplus store in Orange, CA. That paired with a burgundy shirt and red lip color created a look for this “Boogie Woogie Bugle Girl.”
2. Find Your Dress
No, you don’t necessarily have to wear a dress, but your basic outfit is the first step to creating your outfit. Here are some great places to look:
- Unique Vintage ( They also have a collection specifically for Dapper Day here)
- Modcloth
- Torrid – Retro Chic Collection
- Pinup Girl Clothing
- Amazon(great options, but you’ll have to comb through a lot of results)
- DayDapper Expo (hosted at Disneyland the weekend of the event)
I found this amazing dress at Unique Vintage for a great deal. The hat was on clearance, but was perfect for the spring Dapper Day event. I got tons of compliments on this dress!
3. Find Your Accessories
The accessories really do make the outfit. Check out places like Etsy and Ebay to see if you can find authentic vintage accessories. For the outfit below, I found a beautiful fur felt hat on Etsy that I couldn’t resist, then paired it with some matching gloves that I found through a vintage seller on Etsy. The Dapper Day Expo has also been a great way to find unique vintage pieces. The sellers are very knowledgeable and love to share stories.
Accessories to Remember:
- Hats = Even if you’re not a “hat person,” you should try a hat for one of these events. From sun hats to pillbox hats, you’re sure to find the perfect vintage hat to have your outfit shine from head to toe!
- Gloves = If you’re not ready to invest in vintage kid gloves, try some gloves from Daiso! For $1.50, you can score a pair of short gloves or opera gloves to add some classy details to your outfit.
- Hair accessories = If you decide not to wear a hat, be sure to add some bling to your hair. Vintage hair combs, a scarf, or some sparkly hair clips can provide just the right amount of fancy to your look.
- Brooches and jewelry = It’s time to raid grandma’s jewelry box! Add a string of pearls for a simple, sophisticated look, or pin some costume jewelry to your dress to provide that je ne sais quo. Collar clips, brooches, and cameos are great for adding vintage elegance to any outfit.
My 1920s flapper look was a truly DIY outfit. The dress was a shift dress from Old Navy that I added a yard of white fringe to the bottom. I paired it with a velvet kimono that I found at a thrift shop and a string of faux pearls. The gloves were $1.50 from Daiso and the headpiece is a metal headband from the wedding section at Michaels that I hotglued some ostrich feathers to.
4. Add some makeup
I wear makeup about 4 times per year — Christmas, job interviews, and Dapper Day! The best way to add some vintage vibes to your outfit is to add a pop of color to your lips. With today’s trends in matte lipstick and nude tones, you’ll make a major statement with a signature red lip. My absolute favorite lipstick stays on the entire day with minimal touch ups. It is Revlon ColorStay Overtime Lipcolor, Ultimate Wine. No really, you’ll just have to add some of the top gloss 2-3 times that day and you’ll stay ruby red-lipped all day long!
5. Don’t Forget Comfortable Shoes!
At Disneyland, there is a lot of walking. There’s just no way around it. So unless you’re one of those people who can wear 5-inch heels all day long with no pain, you’ll need to consider what your feet will need to survive the day at Disneyland. Opt for stylish flats or oxfords that you can slip a comfortable, orthopedic insole into so that you can last all day walking through the streets of Disneyland. If you opt for a dressier shoe, try a kitten heel to avoid foot pain later in the day. A 2-inch heel is also great for people with flat feet (I’m one of them) because it will alleviate the strain on the arch of your foot. I’ll be rocking some pink wingtips that I found a BAIT footwear that match my dress perfectly.
