Fall is supposed to be the time of year when the weather starts to cool down a bit, but that definitely wasn’t the case for this Dapper Day.  Even though the temperature was almost 100 degrees on Dapper Day, park-goers still showed up in their classy clothes!  Here, we look at some of the awesome menswear that we thought stood out to us!

Mr.  Rosewood

We’ve seen this dapper fella before! Dave has always been one of the most eccentric dressers I know.  He combines vintage clothes with unique pieces to create an incredibly personal style!  In this outfit, he wears an awesome 1940’s pinstripe suit, overcoat, and homburg.  These are traditional and classy items, but he puts his twist on it!  Note his textured tie.  Normally a textured tie wouldn’t be worn with such a conservative suit, but he rocks it well.  It’s always fun to break the rules!

Just look at all those details:  the Foxhead cane, the leather bag, and the vintage spectators.  He was one of the best dressed gents I saw that day!  The best part is that this is his everyday attire; he attends the park always dressed to the nines!  It always makes my day when there are guys who are true to their own style and wear it with pride.

The Barrio Dandy 

Carlos is another vintage menswear cat!  Unlike most of us in the vintage community, he loves combining pieces from different eras to build an outfit! For example, he’s wearing a 70’s jacket, a 30’s tie and collar bar, 50’s gab shirt, and 60’s pants!   Even though its anachronistic, he still looks dapper and exudes a classy image curated himself.  And just like Dave, he’s got some awesome details:

He handcrafts each piece of jewelry!  Just look at all that detail and personality.  His pieces can be bought along with his collection of vintage clothes at his pop-up shop.  Just like me, he is dedicated to helping men find their personal style and offers styling services along with selling the pieces he finds.  I hope we’ll get to feature him more!

Master Reese

Can’t have a vintage event without good ol Benny Reese!  We’ve seen him many times before, wearing only rare pieces from the 1930s-1950s. In this outfit, he’s definitely going for a burgundy vibe.  This isn’t a suit, but all the separate pieces (hollywood jacket, trousers, and spectators) definitely work together.  He’s even got two lapel pins:  one to advertise the Day and the other to advertise his business.  Let’s see what’s on his back:

Boom: it’s belted.  You can even make out a faint pattern on the jacket!  Since he’s got one of the largest vintage collections in the world, its no surprise that he keeps the best for himself!  If you’re ever looking to get some vintage items with all the details (without going bespoke), check him out! 

Classic Blue and Brown

Nothing works together like blue in brown.  In fact they’re my favourite colors!  This gentleman knows what he’s doing, from the fit of the blazer to his perfectly tilted bowler hat.  Brow-line shades are an excellent accessory, as they look good on almost anyone.  Pins seem to be all the rage this Dapper Day, and if you look closely you can see that he’s got two:  A round one and a 60th-anniversary Disneyland one!

The Jazz Player 

This is one of the coolest outfits I’ve ever seen!  If you haven’t been to California Adventure, then you wouldn’t really know that there’s a lady named Dime who comes out in her Jalopy and sings with her five other musicians.  Each of them wear such crazy colors and outfits, reminiscent of the 1920’s.  This outfit is an exact copy of those musicians. All the details are there:  the double breasted vest, striped pants, spectator shoes, and straw boater.  It’s certainly colorful but delightfully pleasing to see in the Parks.  You can tell that this attendee worked hard to create this outfit as accurately to the Disney cast as possible!

Suits Make it Simple

If you’re ever in doubt about what to wear, just put on a suit.  Its already takes care of most of your outfit:  the jacket and pants!  This guy certainly has that down.  He’s already keeping cool with a seersucker suit.  Since seersucker is mainly a blue fabric, he accents this with a deep navy shirt and silver tie, creating a classy yet simple ensemble.  Follow this gent’s lead and put on a pair of statement shoes to finish it off, like these casual wingtips with red laces!  Well done!

Old School Cool

Sweater vests are one thing, but cardigan vests?  Definitely a rarity.  It creates a “grandpa aesthetic” that this gent rocks well.  With a grey fedora, hand-painted tie, and spectators, he definitely exudes a seasoned man straight from the 1950’s.

Combatant Gentelman

I’m not well versed in Military garb, but this guy looks great.  Those boots make the whole look.

Expertly Tailored

A navy blue suit always looks good.  Especially if its expertly tailored with no mother-freakin breaks.  Bonus points for using an actual self-tie bowtie!  His gal is also very well dressed!  Reminds me of the 1960’s!

Smokin’ Velvet

With his velvet waistcoat, paisley ascot, and pipe, this gent should’ve hung out with Jay.  This is a very eccentric look that I love, especially due to his circle frames and curled ‘stache.

Tights, Boots, and Bowties

The guy on the left has the most unique outfit I saw all day.

A Dapper Olaf 

We’ve discussed Disneybounding before and this is a great example of it.  His orange bowtie is Olaf’s carrot nose, his white suit is the body, and the brown buttons are the stones on Olaf’s body!  This gent even has the straw boater from the song “In Summer”!  This is a very classy and well done Disneybound.

A Well Dressed Family

They win my award for the best dressed family.  Check out the gentleman; he’s got a plaid shawl collar dinner jacket.After talking with them briefly, they said that was a true 1960’s tux jacket previously owned by his wife’s father.  Excellent use of keeping vintage in the family!

Sharp Peaks 

Great 1960’s does 1930’s look with a single breasted, grey blue, skinny peak lapel suit.  Dandy points for using a tie pin rather than a tie bar!

Dapper Patriarch and Progeny 

How adorable!  Grey, white, and black always go together.  The father takes these pieces out of the boardroom and into the Park by wearing a gingham shirt and plaid bowtie.  Patterns on patterns indeed.

Short Pants and Short Sleeves

Saddle shoes are the two-tone casual cousin of the spectator shoe.  This gent certainly gets the most out of them by wearing a pair of shorts with his ensemble, rather than trousers.  He even wears a short sleeve shirt with a vest and bowtie!  This look is certainly “geek chic” and perfectly comfortable for the hot weather we had that day.

A Preppy Jose

Okay, Jose from The Three Caballeros was always pretty preppy with his bowtie, boater, and yellow blazer, but this Disneybound in particular is the best one I’ve seen.  Why?  Just look at his jacket; it’s a seersucker jacket with a gingham pattern.  Preppy staples to the max.

A Modern Day Gatsby

A white suit doesn’t have fall vibes but it is certainly appropriate for hot weather.  This gent knows what he’s doing.  He’s got a striped tie with a deep dimple, a watch fob, and perfectly tailored pants that have no freakin’ breaks.

The Rah-Rah Norfolk Suit

This suit has got so much going on that I don’t know what to call it.  It has a center faux belt that looks like a Norfolk jacket, yet it has curved flap pockets like a 1920’s Rah-Rah suit.  Such an interesting and rare suit!

Sharp as All Hell

I don’t know what’s cooler:  his velvet slippers, the camel coloured jacket, or his dark floral shirt.  Either way, he’s dangerously sharp.

Eccentric Details 

A 1920’s four-patch-pocket jacket, tweed vest, square-end bowtie, and tooth gauges?  I feel like he needs to be telling me about his latest safari adventure.  Very well done.

A Fall Palette

Here’s a couple who actually dressed in colors for fall!  She’s got orange and navy blue, while he adds some brown and green into the mix!  It’s tough for most guys to wear orange, but he does it well by working with the fall palette!

 Dots on Dots 

Dotted pants and a dot shirt?  Trendy.  White jacket and spectator shoes?  Dapper.

Flight Attendants and their Captain 

The gent is simple, letting his ladies take the spotlight  with their awesome attendant uniforms!

The Exploring Family 

Simply amazing.  With their pith helmets, khakis, and boots, this family is ready to tackle whatever challenges they find in Adventureland.

Very Well Done, Sir 

Spectator shoes just keep coming back don’t they?  Well this gent certainly knows how to dress.  He’s got a three piece suit, complete with watch fob and collar bar. Note how his tie and pocket square aren’t the exact same pattern and color, but similar.  I’m also digging his round frame sunglasses.

Boater Boy

Another great example of the blue three piece in action.

Workwear Wreck-It Ralph

I love it when people combine Disneybounding and style.  Instead of wearing typical pants and shirt, this guy evokes Wreck-It Ralph’s clothes with a workwear aesthetic, down to the ascot, boots, and flatcap.  Very well done.

White Tie Done Right 

White tie is still considered a tuxedo, but the details and cut are all different.  This man does it well, even donning a top hat too boot!

The Real Photographer 

I think this guy is more qualified than I am to document the style of Dapper Day!

The Haps Mag

Wouldn’t be a Dapper Day without our pals at the Haps Mag!  They’re always well dressed!

The Trendy Designer 

Caught this guy strolling near the Lincoln attraction.  The highly cuffed pants, the round frames, the panama, and the bag make him look like a designer ready to present at NYFW.

Darth Vader and her Bounty Hunter

Here we have the lovely Ischelle (as Darth Vader) and her boyfriend, who is Disneybounding as non other than Boba Fett, the most feared bounty hunter in the galaxy.  Fortunately, he doesn’t do disintegrations.  For now.  All of the Boba Fett details are in the color scheme (brown, green, and red) along with the awesome Mandalorian patches!   As I’ve been saying, the key to style is all in the details.

Last, but Certainly not Least 

What a better way to finish this feature than with this lovely couple?  Even though this gent is wearing suspenders and a belt, he still looks very relaxed and happy to be at Dapper Day! His outfit is simple, but everything works together.  His suspenders, made out of interwoven leather, are especially cool, contrasting against the elastic ones we’ve seen all day.  As we’ve seen many times today, the boater and bowtie were huge staples on Dapper Day, but it comes off as effortless on this gentleman.

Thank you to all of those who agreed to be featured on the blog!  I hope I run into them again for the Spring event!

Always a pleasure,
Ethan W.

Photography by Ethan W.