The Fashions of Dapper Day at Disneyland Pt. I

Here it is.  The most well dressed bi-annual event of the year:  Dapper Day.  This is a day where people go to disneyland dressed  to the nines, whether that be through disneybounding (where you dress as a disney character in normal clothes), going vintage, or just being classy!  Here’s the first part of some of our favourite outfits!

 1. “Hats and Spats” 

Spats are those coverings on the shoes.  They really were useful since it rained for a few hours during the Park!  The man on the left is rocking the top hat and tuxedo while the chap on the right is wearing a genuine 1920’s pinstripe suit!  He looks like he stepped out of Boardwalk Empire.

2. ” Marlin, Dory, and Friend “

There’s not always a good time to wear orange head to toe, but if there was, it’s Dapper Day!  It’s a great way to bound the characters from Finding Nemo!

3. “Dapperly Suburban”

This family was just utterly adorable!

4. “The Three Caballeros”

Disneybounding Donald Duck is probably the only time I’d recommend wearing yellow shoes.  These guys do the Three Caballeros well; they even wear ONLY suspenders!  Tip, if you wear suspenders, don’t wear a belt!

5. “Caps and the Not so Three-Piece”

You can make a three piece look with sweaters or odd (mismatching) vests.  These chaps do it well and finish it with nice driving caps!

6. “Booker and Elizabeth”

These guys take it a bit earlier by going 1910’s by cosplaying the characters from Bioshock Infinite!

7. “Bold and Brown”

This is one of the best outfits I’ve seen! The man’s brown suit is excellently tailored (NO BREAK PANTS)  and is even a nice light shade that we don’t see often!  His shoes are pretty great as well.

8. “Clothes can be a work of art”

Check out her dress! It’s practically a painting!

9. “Preppy Primary Caballeros”

Another great way to Disneybound the three Caballeros!  I am loving the victory curls on “Donald” and the yellow gloves!

10. “The Seasoned Conductor”

My friend Michael rocks the dandy mustache and the conductor outfit!

11. “Victorian Veterans”

They made me feel like I stepped into a dickensian novel!

12. “Boaters and Beaus”

This nautical crew just exudes regatta fashion!  Props to the double breasted man for rocking white pants in the rain!

13. The “Mad Tea Party”

Believe it or not, they are disneybounding the tea cups!

14. “Rockabilly Fleck”

Classic 1950’s style on the man with his amazing flecked jacket and island tie! As for the gal, I love her spectator shoes and the pastel hair and dress.  They’re definitely a greatly dressed couple.

15. “Victory Curls and Bae-Max”

Baes.  I love both looks.

16. “Dem Polka Dots Doh”

 Check out the man on the left; he’s got leather on leather.

17. “Dapper Squad”

Check out the sneaky cruella de ville bound!  Absolutely gorgeous group.

18.  “Pinstripes and Cheetah Print”

This guy caught my eye because he’s wearing a nice 1930’s three piece suit! As for the gal, she rocks the 1950’s with her converse and cheetah print dress.

19. “Peter and Merida”

Love the subtle 1940’s influence in both outfits!

20. “So Bright”

Who said you can’t rock bright colors in the rain?

21. “Pearls and Parasols”

I’m guessing they’re disneybounding as GoGo and Honey Lemon from Big Hero Six just from the colours!

22. “Do I Even Need to Say It” and The “Up House”

Amazing outfits.  The Frozen girls even coordinated their heels!

The true winner is the Up House.  Her hair is blue (sky) with balloons while her dress is the house!  Her shoes even look like the sky, so it’s like the house is flying!

23. “The ‘Up’ Family”

I have no other words other than goals.

24. “The Joneses”

Indy would be proud.

25. “Paired Parasols”

Matching with the parasols is great, but check out the details! The gal on the left has got a great 1960’s Mod look going and the girl on the right has got apples on her dress!

I’m digging the pinstripe suit and the great pattern mixing!  It’s fleck on plaid!

26. “Sunday Morning Suit”

No, he’s not wearing a tuxedo; it’s called morning dress! The girl is rocking an interesting dress with the green sash coming from the collar.

27. The “Colonial Explorer”

I think people should bring back the monocle.

28. “Plaid. That is all”

Those pants man.  Combined with a Willy Wonka top.

29. “Jane, Minnie, Ariel, and Mickey”

It’s always fun to see how people dress up as their favourite characters and still be dapper! This group gets it right.

30. “Explorers and Aviators”

Vintage explorers are awesome.  We got Indiana Jones, Amelia Earheart, and a Safari guy.

31. “Dapper Crew”


The gals on the left stand out because their dresses have such great patterns and fabrics!

32. “Fancy Flappers”

Short hair and pearls are the way to get that flapper look.

33. “Superb Sister Squad”

These women are one of the best dressed I’ve seen.  So many great looks, but I have to say I love the fur collar and hat on the gal in red!

34. “The Fairest One of All”

Great Dapper Day Snow White Disneybound!

35. “Little Black Dresses”

Black is one of the classiest colors and going monochromatic is one of the best ways to go about it.

36. “Gatsby Gals”

Here’s where we get a bit more true vintage with the erm…flappy flaps of the fabric.

37. “Periwinkle Pink”

Monochromatic is cool!

38. “Dapper Aladdin, Jasmine, Tiger Lily, and Peter Pan”

Believe it or not, that’s Aladdin. Aladdin’s purple vest is the shirt, and his fez is represented in the tie and flat cap!

Also check out Peter Pan. Green coat and green spectator shoes!

39. “Giselle and her Dole Whip”

Giselle is a forgotten Disney Princess unfortunately, but I noticed her straight away by the hair!

As for her sister, she decided to bound not as a Disney Character, but as Disney food!  She’s Dole Whip!

40. “The Man Himself”

What strikes me as impressive is his tie.  That particular design on the tie:  STR.  It stands for Smoke Tree Ranch, which was a vacation home he frequented.  Look it up; you can see the real Walt wearing that tie with the emblem!

41. “Cruello de Ville”

Genderbending is often really creative.  This guy pulls it off greatly.  The fur coat and the spectator shoes are the highlights of this outfit (not to mention his highlights in the hair)

Don’t see your self?  Just wait until the next post!  We really loved each outfit we shot.  Just remember, it’s not about being vintage or disneybounding, it’s about showing your style at Disneyland!

Which one was your favourite? Would you wear any of these?  Let us know!


Ethan W.

Street x Sprezza

Photography by Ethan W. and Tim M. 

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