7 Tips for a Successful Dapper Day

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7 Tips for a Successful Dapper Day

I’ve been participating in the Dapper Days at Disneyland for four years now, and it has become something I always really look forward to. For those who don’t know, Dapper Day is an unofficial event (meaning it is not sponsored or hosted by Disney) where guests are encouraged to dress up in stylish clothing and accessories.

Dapper Day started as a throwback to when Disneyland first opened in 1955. Visiting Disneyland was a special occasion and some people would wear their “Sunday finest” – men in suits and ties and women in dresses and heels. Over time the Disneyland dress code has become a lot more casual – trust me, I love my shorts and flip flops – but there’s something fun about dressing nice and having a “special” Disneyland day.

Over the years the event has grown from a small gathering of people at Disneyland, to Dapper Day weekends at Disneyland, Walt Disney World, and even Disneyland Paris! It has been fun to see more and more guests getting involved with dressing up dapper.

Since I’ve attended so many Dapper Days, I thought I’d put together my list of tips and advice for a successful Dapper Day for anyone who is thinking about dressing up for the first time!

7 Tips for a Successful Dapper Day

1. Wear something that makes you feel beautiful (or handsome). I’ve witnessed a lot of people get really, really stressed out about their Dapper Day look. I’ve even heard some people say they have never participated in a Dapper Day because they feel their clothes aren’t “good enough.” Rubbish! Dapper Day is simply a day to step out in style, whatever that means for you. It can be a dress, skirt, pants, a nice top, heels, flats, sneakers … I have seen (and worn) it all.

2. Practice your hair and makeup ahead of time. I am a little bit clueless when it comes to doing up my hair and makeup all fancy. But I wanted to learn a few new tricks for my Dapper Day styles, so I watched YouTube videos and practiced doing winged eyeliner (still don’t have the hang of that one) and experimented with no-heat curls. If you’re not used to doing your hair and makeup in a vintage style every day, then you can’t expected to just wake up on Dapper Day morning and craft the perfect look. You have to practice! Of course, hair and makeup is optional … you’re beautiful just the way you are!

3. Arrive early, if you can. The earlier you can arrive at Disneyland, the cooler the weather will be. And cool weather is great when you’re wearing heavy clothes or lots of layers. Spanx + heat do not mix. A bonus to arriving early – less guests in the background of your photos!

4. Make sure you have plenty of space on your phone, and you have an extra external charger. Speaking of photos, Dapper Day is a day to see and be seen. You’ll probably want to take a lot of photos, not only of yourself but of other lovely guests as well. So be prepared!

7 Tips for a Successful Dapper Day

5. Check out the expo if you really want to immerse yourself in Dapper everything. For the last couple years, the Dapper Day expo takes place at the Disneyland Hotel. For a small cover charge, you can shop tons of vintage clothing and accessories & small shops, pose for photo ops, purchase a cocktail, and dance to a live band. It’s a lot of fun!

6. Bring comfortable flat shoes in your bag. Trust me on this one.

7. Be friendly and complimentary. One thing I love about Dapper Day is everyone is so friendly! Expect to get a lot of compliments on your look, and don’t forget to return the compliment. Offering to take photos for people or gushing over someone’s fabulous faux fur wrap will make a fun day even better.

What’s your favorite Dapper Day tip?