This past weekend, I had the absolute pleasure of attending Dapper Day at the Disneyland Resort, and I’m still riding high on vintage vibes and warm fuzzies! If you’ve never been, Dapper Day is more than just a fashion event—it’s a celebration of timeless style, creativity, and community. Whether you're a vintage enthusiast, a Disney lover, or just someone who appreciates getting a little fancy, there's truly something magical about it.
Picture of the Dapper Day expo Booth with so many wonderful goodies!
What Is Dapper Day?
Dapper Day is a fan-organized event that celebrates refined style from yesterday and today. Guests don their best vintage-inspired outfits—think mid-century fashion, retro accessories, pin-up glam, classic suits, and so much more—and stroll around Disneyland Resort looking like they’ve stepped out of a time machine (in the best way possible). It’s a chance to step into your most stylish self and connect with others who appreciate the same era of elegance. This may have been the last Dapper Day Expo as they may not be able to hold the dull expo in the future, but the event will still be happening in the future. I recommend signing up for their email lists to stay up to date! DAPPER DAY
How to Dress for Dapper Day
Dressing for Dapper Day is half the fun! Think swing dresses, circle skirts, high-waisted trousers, suspenders, and bow ties. But don’t forget—comfort is key! You’ll be walking, exploring, and probably posing for a lot of photos, so make sure to balance style with practicality.
Here are a few of my go-to tips:
Comfy Shoes Are Your Best Friend – Cute vintage-inspired flats or low wedges can still be stylish without sacrificing your feet.
Add Some Flair – Brooches, gloves, parasols, fascinators, and statement jewelry can elevate any outfit.
Pack Light, But Smart – Bring a stylish tote or clutch that holds essentials like lipstick, a compact mirror, a fan, and a small water bottle.
Dress in Layers – The weather can be unpredictable, especially in spring, so a lightweight cardigan or cropped jacket is perfect.
Vintage doesn’t have to mean “old”—there are so many modern brands creating retro-inspired fashion, or you can go full authentic with true vintage pieces if that’s your thing!
If you want more thoughts and ideas on how to dress vintage check out this previous post! Kaytie Martinez Photography - Vintage Fashion Tips: How to Perfect Your Timeless Look
The Dapper Day Expo: A Vintage Wonderland
The Dapper Day Expo was buzzing with energy and creativity! It’s one of my favorite parts of the whole weekend. The expo hosts dozens of small businesses and boutique brands that cater to vintage lovers, rockabilly babes, Disneybounders, and dapper gents alike.
There were mini concerts, swing dancing lessons (so fun!), and rows upon rows of treasures to browse—from retro dresses and replica clothing to unique accessories and original artwork.
A Few Booths That Stole My Heart
Here are some of the standout booths I adored visiting:
The Star Brite Motel
TheStarBriteMotel - Etsy
This booth was pure 1950s charm! I couldn’t resist one of their Disney-inspired brooches that matched my outfit perfectly. Their accessories are the perfect blend of kitschy, cute, and classic. Kimi was so sweet to talk with and her booth fit her personality perfectly!
TheStarBriteMotel - Etsy
This booth was pure 1950s charm! I couldn’t resist one of their Disney-inspired brooches that matched my outfit perfectly. Their accessories are the perfect blend of kitschy, cute, and classic. Kimi was so sweet to talk with and her booth fit her personality perfectly!
Rock A Belly
Website: Rockabelly
This booth had me swooning! I loved the “rockabilly mama” theme. As a mama myself with a deep love for all things retro, this one really spoke to me. I picked up a stunning headscarf—ideal for those no-hair-day days when you still want to feel cute and put together.
Website: Rockabelly
This booth had me swooning! I loved the “rockabilly mama” theme. As a mama myself with a deep love for all things retro, this one really spoke to me. I picked up a stunning headscarf—ideal for those no-hair-day days when you still want to feel cute and put together.
Kellsworth Ink
Website: Kellsworth Ink
Kelley Frisby’s artwork is so whimsical and thoughtful. I found the sweetest hand-drawn card for my bestie, and I cannot wait to gift it to her. There’s something so special about handmade art that feels personal and heartfelt. Kelley was so sweet and I loved chatting with her about her unique designs and style.
Website: Kellsworth Ink
Kelley Frisby’s artwork is so whimsical and thoughtful. I found the sweetest hand-drawn card for my bestie, and I cannot wait to gift it to her. There’s something so special about handmade art that feels personal and heartfelt. Kelley was so sweet and I loved chatting with her about her unique designs and style.
Girl With One Eye Fashion
Instagram: @girlwithoneeyefashion
Kimberly was an absolute delight to chat with. Her passion for her designs shone through every piece. All her clothing is made in small batches right here in Los Angeles, and there’s something for every unique personality. She sells you whole outfits from the clothing itself all the way down to the accessories to make it complete! You can tell every stitch was made with love.
Instagram: @girlwithoneeyefashion
Kimberly was an absolute delight to chat with. Her passion for her designs shone through every piece. All her clothing is made in small batches right here in Los Angeles, and there’s something for every unique personality. She sells you whole outfits from the clothing itself all the way down to the accessories to make it complete! You can tell every stitch was made with love.
Sey Studios
Website: Sey Studios
Whimsical, vibrant, and full of joy—this booth was a colorful escape. Sey’s art just makes you smile. Every print and product radiated warmth and happiness. One of the best touches she has is that her business card is a coloring page too!
Website: Sey Studios
Whimsical, vibrant, and full of joy—this booth was a colorful escape. Sey’s art just makes you smile. Every print and product radiated warmth and happiness. One of the best touches she has is that her business card is a coloring page too!
So This Is Love Designs
Instagram: @sothisislovedesigns
For my fellow Disney nerds, this booth was a dream! Custom hair fascinators and the cutest little pouches for on-the-go organization. It was Disney-inspired magic with a chic, handmade twist.
Instagram: @sothisislovedesigns
For my fellow Disney nerds, this booth was a dream! Custom hair fascinators and the cutest little pouches for on-the-go organization. It was Disney-inspired magic with a chic, handmade twist.
1. The Star Brite Motel Booth at the Dapper Day expo. So many cute broaches, pins and jewelry!
2. Rock A Belly booth! Such a great idea of providing vintage styled clothing to the vintage mama!
3. Kelley Frisby's booth. She makes such beautiful and whimsical art work!
4. Girl with One Eye Fashion. This booth was full of unique items to wear and accessories that complete an entire outfit!
5. Sey Studios Booth. Sey had so many cute products, broaches, and even coloring books!
6. So this is Love booth. They had so many wonderful items to sell, pouches hats and accessories.
My Favorite Moments
There’s nothing quite like being surrounded by so many people who are dressed to the nines and just living their best vintage lives. I loved chatting with other attendees, swapping outfit compliments, and feeling the camaraderie that comes with being part of such a fun community.
We didn’t go into Disneyland itself this time, but the Downtown Disney District was lively and full of charm. I especially enjoyed the newly renovated area near the live stage, where we caught some swing dancing lessons on the grass. Music, sunshine, and joyful energy—it was such a vibe.
My Dapper Day Outfit: Disneybounding the Disneyland Hotel
For this Dapper Day, I chose to Disneybound the Disneyland Hotel—yes, you read that right! Disneybounding is a playful way to dress inspired by Disney characters, locations, or themes using regular clothing instead of costumes.
To channel the hotel’s sleek mid-century aesthetic, I wore a blouse and pencil skirt combo in blue, and a hand made (by me) peplum skirt overlay with beautiful embroidered white stairs reminiscent of the hotel’s iconic color palette. I added a vintage “D” pin mentioned above, pearl earrings and necklace, and a handmade floral hat(made by me again). It felt classy, nostalgic, and totally on theme! A lady stopped me and told me that my outfit looked beautiful and simplistic retro beauty!
Picture of Kaytie dressed in her 1950's styled outfit Disney bounding as the Disneyland Hotel. Kaytie is also wearing cat eyed glasses and a handmade vintage styled hat with blue and white flowers.
Picture of Kaytie dressed in her 1950's styled outfit Disney bounding as the Disneyland Hotel.
Picture of Kaytie dressed in her 1950's styled outfit Disney bounding as the Disneyland Hotel. Image of the pin she bought from the Star Brite Motel booth!
Tips for Making the Most of Dapper Day
Plan Your Outfit in Advance – Give yourself time to find or create the perfect ensemble.
Stay Hydrated & Bring Snacks – Especially if you’re spending the day walking around.
Make Time for the Expo – You’ll discover so many hidden gems and amazing creatives.
Be Social – Compliment strangers, take photos, and strike up conversations. It’s all about community!
Don’t Stress – Whether you're in full vintage gear or just a hint of flair, the day is about fun, not perfection.
Final Thoughts
Dapper Day was everything I hoped it would be—vintage glamour, creative inspiration, and quality time with people I love. It reminded me why I adore retro fashion and small business creativity so much. If you ever get the chance to attend, go for it! You’ll walk away with new treasures, fun memories, and maybe even a few new friends. I so look forward to attending the Fall Dapper Day this year!
Have you ever been to Dapper Day? I’d love to hear what you wore, what you loved, or what you’d be excited to try next time! Until next time, stay dapper ✨
Kaytie
Kaytie
