I Didn’t Know What to Wear to the Medium Holiday Party, Or “How My Style Defines Me, Kinda”
It is Saturday night. I am at my favorite haunt, Why Not in LES here in NYC. It’s a seasonable 46 degrees. Look at me sounding like a damn meteorologist telling a story. I still don’t know what to wear to the Medium holiday party. The party is on Monday. I’m not nervous, not even a tad bit anxious.
But, I care about these things. Do I care about domestic terrorism and ISIS running amuck and the NRA’s tight grip on our congress and Donald Trump “Donald Trumping” us? Yes, absolutely. I also care about clothes. A lot. So much so that I am currently sipping an iced coffee wondering if I’ll be judged by what I choose to put on my body for what could be a formal or mad informal holiday shindig. Because I am the man who believes these kind of decisions make or break how the world views you. Far be it for me to be the Black schlub who shows up in some cool ass Saturday Surf sweats and a henley trying to be too festive but too cool to be festive. You know, the kind of “oh this? I just threw this on” kind of look. I would say that while I flipped my hair back, if I had hair. I do that in the shower sometimes. I fake imagine (that’s a double imaginary sequence) I actually have hair and I flip my bald headed ass head back and act like I’m Tom Cruise in Top Gun, way before Goose dies. That was some sad shit. I want to be Tom Cruise in Top Gun at this party, but the Black version. So really, I want to be the light-skinned version of Idris Elba as Tom Cruise in Top Gun at this holiday party. Because Idris Elba is a dope ass dude who woulda killed in Top Gun. Actually, he might be better suited as Val Kilmer’s “Ice” character. Maverick isn’t Idris’ angle, I think. So, I’m back to just being the light-skinned Black version of Tom Cruise in Top Gun at the holiday party. I wonder if I’ll give off that kind of vibe. We’ll see.
I was in Urban Outfitters today. I am 32, a newly crowned father, and I still shop at Urban Outfitters like I just got my financial aid check before Spring Break. But, fuck it. I feel comfortable there. Plus, they have great sale stuff, little nice and essential closet pieces to add to my evaporating wardrobe. I made a joke on Twitter the other day that I thought I had more books than clothes and how I wasn’t sure if that was a problem or not, and someone assumed it was some sort of elite posturing I was doing. Slow down shun, I’m as serious as a heart attack. Ah, there I go, showing my age again. Only old Black uncles say things like “as serious as a heart attack”. Or, even better, you rhyme phrases together in casual conversation like, “girl if you can’t sow it, ya’ better show it” or some type of other lingo that will never make sense, no matter what context you place it in. So anyways, I’m in Urban Outfitters because I’m looking for something to wear to the Medium Holiday party. I think Matt Higginson may have been drunk butt emailing me, but I got an email with an invite to a Medium holiday party. And as the kid who didn’t go to a real party until college, I absolutely salivate when I get invites to do cool shit with seemingly cool people who think I’m cool enough to be cool with them. And I got a black suit, right? And I got a couple of blazers, some chinos, but you never wanna be too over dressed or too underdressed and so therein lies the rub. Needless to say, I’ve come a long way as far as my wardrobe goes.
My fashion choices have changed dramatically over the years. Long gone are the way too baggy for my then skinny ass self jeans and the “Jay Z said get rid of the throwback jerseys so I’ma cop this way too big French cuff spread collared shirt” days. You learn a lot when your former fiancé graduated from FSU with a fashion degree and worked at Details for some years, and you actually read GQ magazine AND scour both the ads and pages for looks to mix and match in ya’ wardrobe (take notes: if you’re a man, and you’re not mix and matching looks you already have in your closet, you’re missing out. Collared shirt over the henley, with some joggers and a mid-top sneaker? Go ahead. No rules). I now have a very serious mental picture of my closet. Back in the day, my closet wasn’t really MY closet but rather, whatever clothes I could steal out of my brother D’s closet after he left for work. D was never a color blocker, heck still ain’t. Blue fitted cap? Sneakers better have some blue in ’em. Shirt too. He ain’t find a color he didn’t want to make sure matched to a tee. Hip-Hop fashion kind of called for it in those days. The young kids now, though? Half of the shit they pull together is half runway/half SoHo/half hobo (I know the math doesn’t add up. Whatever), and it’s kinda dope. Fashion now reminds me of fashion in the late 70’s and 80’s, where risk taking seemed to be the status quo option when it came to what you left the house in. The latter part of the 2000’s ushered in a new era of basically the old era, with a new guard in charge of its appearance.
I started pin-rolling my pants in 2014. Joshua Kissi of Street Etiquette is from the Bronx, running into him on the train or seeing him spread out across the New York Times always brings me a sight of joy. He and Travis put out a “how-to” for pin-rolling pants type deal. I was doing it before the video, but I felt like I was doing something right. If you’re from the hood, or as Jay Z kindly ad-libbed “the hood-hood” then you know a slightly closer fitting tapered leg and a pin-rolled pant on the 4 train going past 161st st., will undoubtedly make you a target for a snicker or two, mainly coming from the “I still wear Wheat colored Timbs to every function and if I can’t wear my Timbs I ain’t gonna be there” crowd. I had a girl tell me once I dressed like a “White boy”. This is the crux of my dilemma. You grow up being told who you are, and what you are or who you choose to be, is a direct reflection of your style choices, and that said style choices indicate where you fall in the race draft. And it is with that that I sit stuck at what to wear to a party with people who will more than likely not care about what I wear, but more about who I am. And this is hard because I come from a place where what you wear is EXACTLY who you are. And that is something I’d like to believe I am okay with. I mean, it’s the holidays and such. And folks will probably be tipsy and talking about whatever folks talk about at the offices at a place like Medium, so there should be no need to worry about a Windsor knot skinny tie choice or a bowtie or the kind of socks to sport or what have you. Fashion has kind of always been something I took seriously, studiously watching NYC’ers float on streets in trenches and bombers and beanies with cap toes and moccasins or pleats because pleats are back and five panels with scarves tucked into quarter zipped mock necks, jogger pants hugging ankles. New Yorkers even hold coffee cups with style.
It’s this kind of thinking that has me questioning what I should or shouldn’t wear to this thing. And a part of me thinks I’d like to be the guy that didn’t give two shits about what others think of my physical. And the other part? The other part is glad that I do. Because to me, that means that I know I’m a part of the world, and how the world sees me matters, which means it matters to me how I carry myself, and how I carry myself isn’t limited to thoughts and actions, but what shoes are more appropriate to wear to a function where there will more than likely be glasses of wine and delectable finger food. Because now I just wear what feels good on me and to my body, rather what I think I’m supposed to wear. I still have my red Vans with the meteor size whole in the back of BOTH feet, along with the Ben Sherman oxford shoes that flap a little in the soles because hey, they feel good and vintage-ey when I put them on, so fuck it. But that doesn’t mean I’m not aware of what the proper attire should be. A good part of rule breaking is knowing the rules to begin with. The last thing I need is Paul Newman crying in his grave, or Nick Wooster pouring out liquor for the clothes on my back. If they take pictures at this fiesta, I want my little Lilah to look back twenty years from now and say “my dad cleaned up pretty swell back then”. She probably will not use words like “swell” or phrases like “cleaned up” but I’m cool with that.
I just emailed Matt asking what he planned on wearing. Yup, I care about shit like this now. I think I’m okay with that now. Finally.
P.S. I decided to wear this (see below). Oh, and I took a picture with Deray and his blue vest. Because #BlackLivesMatter. And the finger foods were mad delectable. Who does pulled pork at a holiday function? Medium, Medium does. The end.
*sings Boys II Men’s and Brian McKnight’s rendition of “Let It Snow”*
*also “Donald Trumping” is when you say things out of your mouth that are irrational, stupid, ignorant, and very much Donald Trump like*
