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Dapper Day Weekend: Perfect Pinup Looks for Disneyland!

Dapper Day Weekend: Perfect Pinup Looks for Disneyland!

Posted by Janine Valentine on Sep 22nd 2015

Hi there guys and dolls!

I just got back from spending two magical days at the happiest place on earth: Disneyland! As many of you probably know, Dapper Day just concluded this past weekend. Dapper Day is Disneyland's semi-annual event that caters to attendees adorned in sophisticated fashion of yesteryear, contemporary formalwear is also welcome. It was my very first time experiencing the soirée, I’m excited to share you how I styled two different looks and my tips for staying comfy without compromising style at Disneyland.


For Dapper Day I had the pleasure of wearing the Sara Dress in Royal Blue, which coordinated perfectly with the park’s 60th anniversary décor. This piece fits the body like a dream; it’s incredibly stretchy and had a nice full skirt (I did a fair share of spinning all day in the park). I wore a canvas underskirt for a little structure, however the dress looks fab without one too!

DSC00169 I ended up wearing a pair of BAIT kitten heels in a soft sky blue and ivory. If you’re not too fond of wearing a kitten heel all day at Disney I’d recommend slipping on a pair of ruffled socks and white Keds or saddle shoes, this is a marvelous option to maintain a retro look…without the potential of experiencing any discomfort.


Since it was Dapper Day, naturally decided to stick with a traditional pinup makeup look which utilized: Ardell #122 lashes, MUFE gel liner, Kat Von D’s Shade and Light Palette, NARS blush in Taos, and Lime Crime’s Red Velvet. Liquid lipsticks are perfect for amusement parks, (I only had to do one touch up).DSC00183

I topped things off with a high ponytail and a houndstooth bow for some balance. Most pinup loving gals are quick to reach for silk flowers; but fascinators, bows, and even hair combs can also bring a classic look to life too.


Toting a big purse around Disney all day can take a toll on your shoulders, so I opted for a pearly hued coffin handbag. I have the same one in black, the purse also comes in sparkly red and a powdery pink. These bags are great for ladies who want a nostalgic purse with a subtle Haunted Mansion vibe. If you’re planning on bringing snacks, a camera, and other effects you might want to consider a cute structured backpack like this one.



Since the park is decorated for Halloween, I decided to do a darker Nightmare Before Christmas inspired look for day two in the magic kingdom with the Sarina Button Slit Skirt and the Keyhole To My Heart Blouse. The white buttons and trim coordinate so well together; several people assumed my ensemble was a dress! This look is super versatile. I wore squishy black ballet flats with a big bow; however all black Vans or even creepers would look killer too.


I kept my makeup limited to powered, winged liner, a little blush, lots of mascara, and a velvety black liquid lipstick (Kat Von D’s Witches). My best tip for those interested in experimenting with bold lip hues is to keep your eyes neutral, I opted for a simple 1960s cat eye.

DSC00274DSC00282 For accessories I ended up wearing a blue orchid duo for a little pop of color from VintageBox 1947, but switched to an R2D2 mouse cap to get into the Disney spirit. I topped the look off with faux pearl earrings, and my trusty Lucite cat-eye sunnies.

DSC00244 (1)


Since it was sweltering all weekend I made sure to carry my trusty black and white fan along with me; handheld fans are an excellent way to stay stylish while cooling off; I always keep this little guy in my purse. Despite wearing all black in the blazing sun, I found the fabric on both the skirt and the blouse to be very breathable. Most pencil skirts have a high slit in the back, but I was pleasantly surprised to see that the Sarina exposes just a little side thigh. I was worried that a pencil skirt at the park would be binding, but I didn't have any trouble dashing around the park or getting on rides (not even Splash Mountain).


That's all I have for now folks! Do be sure to keep tabs on all of my misadventures on Instagram and on my blog, Darling Valentines. A huge thank you to my awesome photographers Melanie Zombie and Diana Rouge.