This weekend, Disneyland Resort will undergo an amazing fashion transformation. For two days, the park will host thousands of well-dressed ladies and gents from all walks of life, laughing, dancing riding rides, looking good–the only way to really describe the event is “dapper.”

We’ve already given you the lowdown on Dapper Day’s origins and what the event is all about. Now that we’re a week out from the two-day event at Disneyland, we’re going to breakdown the secrets to actually achieving a Dapper Day look, with help from the event’s creator himself,┬áJustin Jorgensen.

One of the Dapper Day basics is that there are no rules; the goal is just to be a little more fancy, a little more–well–dapper. “The spirit of the day is about dressing it up a notch, so simply swapping cargo shorts and tee for a bright polo and pants is great,” Jorgensen explains.

How to create your Dapper Day Outfit

Many folks who attend also use the day as a chance to show off their love of a certain period of dress, so to their slightly fancier outfits, they also add some vintage or retro flair. As you’ll see when you arrive at the Park, some attendees go all-out with entire ensembles specific to a single decade. If your ambition exceeds your ability or wallet when it comes to a vintage look, you can always add retro touches with thrift store finds or vintage-inspired costume jewelry. As we plan our Dapper Day ensembles, we’re matching dresses from our closets with retro gloves, dats, and broaches in order to get a subtle late 1950s vibe.

How to create your Dapper Day Outfit

Jorgensen also recommends adding a little pop of color where you can. For the best photos of the day, he claims adding some color to your outfit is a must: “Getting some color in the mix is key and you can easily do that with accessories.”

One piece of advice that can’t be overlooked is that, though you’ll look fancy, refined, and retro, you’ll still be at the sprawling Disneyland Resort, so we also recommend being practical i.e. shoes that look good AND are capable of being walked in.

Dapper Day Shoes

Girls sometimes have it easy since we can add gloves and a vintage clutch to an outfit we already own to achieve dapper status. Sometimes guys have it a bit tougher since modern clothes aren’t always tailored and cut in a silhouette that lends itself to being a little fancier. For this, Jorgensen recommends some old standbys: “Places like H&M and Forever 21 have lots of colorful and very affordable blazers for guys.” Adding a vest or jacket to an everyday outfit, plus the right hat or pocket square might be all you need to take your typical Disneyland trip to Dapper Day levels.

How to create your Dapper Day Outfit

If you’re still at a loss as to how to dapper-ify yourself in time for this weekend, be sure to stop by the Dapper Day Boutique at the Grand Californian which will host vintage and contemporary designer dealers with items dating back the last hundred years. Jorgensen makes the boutique sound like a must: “We’ll have everything from classic mid-century Chanel to more avant-garde standouts like Junya Watanabe and Margiela. And of course loads of accessories, hats, bags, glasses, etc.”

Finally, our last piece of advice is to have fun. There are no right or wrong ways to do Dapper Day, so embrace whatever decade, style, or colors are your favorite, and be sure to take plenty of pictures!

Posted 6 years Ago
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