Dapper Day – Orland, FL

What better way to guest blog on here but to cover Dapper Day here in Orlando! I know, about a month late but who doesn’t like remising on such a magical day? This year was truly a special one as well! Instead of being held at Disney’s Hollywood Studios it was held at Epcot due to Hollywood Studios being under so much construction leaving less than half the park available to people visiting. (But who can’t wait for Star Wars Land and Toy Story Land?! I know I can’t!!) Even better, we got to have our own mini Expo! This was something that I’ve been eager to see over here.




About 90% of my outfit was vintage bought at various shops on Etsy and in Orlando. The dress was bought of Etsy but the hat, gloves and purse were bought at a vintage shop. The dress came with a sash to tie in the back for a bow but that didn’t work out for me so I decided to wear it as a kind of scarf, reminded me of Grace Kelly. The coolest part of my outfit, to me at least, was the purse because it came with a small mirror attached on the inside so you could check your lipstick whenever you needed! So cool, right?!?




I was accompanied by Kasi (@pinupbarber), her husband Elliot and my boyfriend Jade. Kasi was sweet enough to buy my ticket to the Expo before it sold out. The park was very crowded that we ended up parking at Hollywood Studios then took the boat over. We went straight to the Living with the Seas lounge where the expo was taking place. What makes this even more amazing is the fact this is a place that rarely sees the public eye. It was beyond gorgeous. As soon as you walked in you were welcomed to a huge aquarium that took up the whole back wall of the lounge. There were drinks and hors d’oeuvres being served. Pinup Girl Clothing and Orlando Vintage were there selling goodies! In the back part of the lounge, there was a photo background set up that you could take photos with, which we gladly took advantage of. We met so many other lovely ladies there, some I knew and some Kasi knew. We ended up with a whole group of wonderful looking ladies at once. The whole event lasted only a few hours but it was beyond perfect and I truly hope they decide to host another one.




When we got out from the expo, it was time to eat around the world for the Food & Wine festival. The Food & Wine is probably one of the best events that Disney puts on. They have so many different booths from around the world serving tapas style food and drinks, so you can be sure to try tons of different food. Once the sun started to set, Jade and I headed next door to take pictures at the Boardwalk Resort because it’s just drop dead gorgeous there. Towards the end of the evening we went to Beach Club resort to eat at their soda shop style restaurant, Beaches and Cream. It was truly a perfect way to end fall Dapper Day.

Thank you to the beautiful Holly Mae Woods for inviting me to guest blog for her. Be sure to check out her guest post on my own blog The Dapper Dames. If you want more Walt Disney World adventure be sure to follow me on Instagram @miss.cara.astaire


Until next time!

-Cara Astaire


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