The king returns.
Dapper Day will always have a special place in my heart. For those of you who don’t know, it’s a fashion event that brings people together and encourages them to dress up! It’s not an official Disney event, but its first outing was at Disneyland. The whole event can come off as little silly compared to the trunk shows, fashion podcaster parties, and NYC hangs I’ve written about in recent years but don’t get it twisted— I love Dapper Day.
The menswear bubble can be wrapped up in its own world, being a little bit serious at times. I like Dapper Day because it’s an “escape” from that side of fashion, being a super accessible event that anyone can attend. The wholesome spirit of Dapper Day is certainly admirable, as it provides attendees an opportunity to dress up however they like: formally, vintage, a bit of cosplay, whatever it happens to be. As I’ve come to think of dressing as an exercise in personal costuming, I like that this event is the best place to be creative with your style. The fact that it’s vintage inspired and semi-involves classic clothing is a win for me!
You might consider Dapper Day an occasion. Not in terms of formality, but in that the event provides an opportunity to dress up in a way that’s different than our normal attire. For years, Spencer and I have attended nearly every outing each event has always been our favorite to dress for; we either wear something new or get a bit dandier than we normally go for (but in a way that still feels authentic to us). We also want to make sure its in line with our actual taste and is still conceivably something we could wear on a non-Dapper Day day.
Since we were working in retail during that time, Dapper Day afforded us an outlet to get really fun with our clothes. I’m sure the whimsical nature of Disney (despite not being affiliated) also allows for some fun. You don’t really get that same vibe with a typical menswear event. Of course we’re all older now. We’ve gained the confidence to wear our “dapper” clothes outside of just Dapper Day; I’m now [affectionately] known as the suit guy at my local bar trivia place. Everyday is an opportunity to dress up, especially since the pandemic has all but done away with dress codes and context. That’s where Dapper Day comes in with its own energy to match with your outfit. Think of it like the symphony: I get to celebrate Dapper Day. This was a true occasion to dress for, being a step above the occasion of grabbing KBBQ or going to boba cafes.
So as you could probably expect, I was pretty excited to pop in after being AWOL for two years. Every outing that they’ve had since 2020, Disney or not, has landed on a day I’ve been busy. I guess a new career, new girlfriend, and a few new friends really have had their toll on my social life! This Fall 2022 event landed on a free day. And after two years of introspective blog posts that lean on the faux-philosophical/critical, I was ready for something that was purely about wholesome fun!
Unfortunately all of my friends that would typically come to this thing (AKA Spencer and MJ) were both busy. I could only go Sunday, as Saturday was the Flea Navidad sale; Spencer and MJ are always booked on Sundays. But hey, that was okay. Isabel was interested in going…and it was going to be her first time at Dapper Day. It was also going to be her first time in Downtown Disney!
I’m not going to lie— I actually struggled with putting my outfit together. It wasn’t because I had decision fatigue but rather the opposite: I had too many ideas! At least the symphony brings me to black tie; Dapper Day has no rules, which is why all my outfits have been on every end of the vintage-inspired spectrum ever since I started attending. What could I wear that would make it more fun than what I wear on a day to day basis? Has my sense of occasion been lost since I wear a tie almost every day of the week?
Thankfully Isabel suggested we Disneybound with our outfits; she was probably still inspired by our fashion-friendly Halloween costumes. I know that Disneybounding can get a bad rap in my fashion circles, but I still find it a fun exercise especially when you have an interest in genres of fashion. After all, I use my clothing to be a “character” of sorts everyday. Also, dressing in the scheme of a Disney character just makes sense for Dapper Day!
As you can probably tell above, Isabel dressed as Briar Rose. She had a brown long sleeve crew neck, a white sport shirt, and a dark denim dress; she also had a dark red cardigan that she tied around her shoulders. The result is a very 1960s prep take on the character. Absolutely perfect mix of items for Dapper Day!
Mine is a bit more vague, but I approximated Prince Philip who really wears something close to what Briar Rose has on: a black tunic and a brown vest/skirt/pant combo. I wore my black sawtooth shirt (my only black button down) with a black foulard and navy sweater vest to allude to Philip’s tunic, while my brown separates (Brooks Brothers sack jacket and rayon pants) vaguely echo the rest of Philip’s attire. I also wore a fedora, which put the whole thing in a very 1930s movie star or European illustration vibe. I loved it. Black and brown is one of my favorite combinations, but I typically wear it whenever its a Going Out look. Turning into something more Esquire Man was the key to make it Dapper Day appropriate! It probably helped that this Dapper Day had milder weather than any of the previous ones; I used to die while wearing tweed and flannel. This outfit was perfectly fine the entire time.
Obviously we didn’t go into the Parks proper (if I’m going to pay for Disneyland ticket, I’m going to go in jeans and sneakers), but we did spend a few hours at the expo. It was just as big as I remember. The floor was full of different vendors selling their wares ranging from true vintage items, reproduction clothing, pomade, shoes, and services like a tintype photo booth, makeup, hair, and tattoos. I especially liked the vintage selection as most of the vendors obviously sold more “formal” items in keeping with the theme; certainly a contrast to the milsurp, workwear, and general Americana found at flea markets (as well as most LA vintage stores). I ended up copping a few things, all in between people watching, listening to live music, and catching up with a few old friends.
I honestly had such a great time. I think I’ve gotta get the guys out here again (even if it’s just for buying vintage)!
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