Dispatch No. 2: The best alliance in hip-hop
What's coming up week of 2/1 and the best alliance in Hip-Hop
Good Sunday to you, HSS Community!
As I sit down to write this in the early morning, snow is beginning to fall. I took Coco for her walk just after 7 a.m. and the flurries began just after. Based on the latest forecast, we are expecting about 12” of snow, which I am very much looking forward to. Being from the Northeast, I have always had an affinity for the colder weather and especially the snow—I guess it reminds me of home and growing up and snow forts and sledding with friends down the big hill that was just a short trek from all of our houses in the neighborhood.
I just think it’s so beautiful too. There is a tree outside one of our upstairs windows in our house that I love catching a glimpse of bright red cardinals sitting in when the snow is falling and completely covering the ground.
Let me enjoy those thoughts for the moment and just forget about the inevitable nasty black snowbanks and slush that follows…

Anyhow, after Coco’s walk I went out back and split some wood so that we’d be topped off inside for a couple fires in the fireplace today and tomorrow. I highly recommend this kindling cracker… We’ll have to figure out when to work the fire in since Coco will definitely want to romp in the snow and I’ve got to hit the rowing machine at some point. I did take a little hiatus from the rower over the holidays but I’ve gradually been working back into it. If you’re interested in connecting via the Concept2 Logbook, hit me up—my ID is 1372114.
Also, I received this prototype garment from Mike yesterday for a white tie fitting…
What’s on tap this week?
TUESDAY: 7 Outdated Men’s Style Rules To Ignore
Can I just say that the very idea of men’s style rules is super annoying to me? I mean, don’t get me wrong, there are some principles that are good to know and learn and practice. But if you’re living your life—please remember that we’re talking about style here—in a constant state of fear of “getting it wrong”, you’re honestly completely missing the point.
I’ve only made one “style rules” video before and it had to do with black tie, which I think is one of the few times that so-called rules really can (and should) apply.
But, if you’re here reading this, you probably already know that I view rules as guidelines above all else. There’s a reason some things “work” and some don’t. In a lot of those instances where we’re talking about something that works, that’s what will generally get codified into a “rule”.
However, there are some rules that are just out there in the ether that I get questions about constantly. So Tuesday’s video is a chance to lay all of them out—some are perhaps a little arcane—tell you where the rules came from and why people thing they should be followed as well as to share some tips and strategies for breaking those rules.
And as an added bonus, I’m finishing off with the one rule I think you should always follow.
THURSDAY: What I Wore This Week—7 Winter Casual Outfits
A lot of the outfit videos we do on the channel are focused on helping you dress for a particular situation or occasion. Because they tend to be “instructional” (and also inspirational) in nature, they’re not generally reflective of what I wear on a day-to-day basis. That’s not to say I never wear those outfits—because I do!—but I think it’s fun to occasionally give you a snapshot of my “real life” daily outfits. I did a version of this video in the fall as well and I’ll probably continue doing them seasonally. You’ll have to let me know if you like the format, which we switched up just a bit!
What’s coming up?
We’ve been operating at a blistering pace, maintaining a two-video/week posting cadence since the beginning of the year. Taking a step back to appreciate that and the hard work of the team to make it happen is appropriate, especially given the fact that this is not a full-time gig for anyone.
At the time of this writing, we’re through post-production and scheduled out through mid-February. But I must admit that it’s taking a little bit of a toll (at least on me!). We had our March—yes, March—production meeting earlier in the week and we've actually set our entire March and April editorial calendars.
There have been a couple of last minute shifts we’ve had to make for the remainder of February and although it’s possible we might pivot to one video per week to close out the month (with the intent of getting ahead on the “easy” stuff into March and April), we’re exploring some creative and “experimental” ways to keep up our Tuesday-Thursday schedule.
Whatever we end up doing, I just want you to know that our focus is always on producing something of quality that provides added value—not simply doing something just to do something or repurposing existing content created for other platforms. There’s a reason people use and engage on different platforms, right? Personally, I never like when I’m served the same content in various places. I mean, I understand trying to maximize your ROI when you’re producing a piece of content. But from a creator standpoint, that just seems kind of lazy. So that ain’t happening here.
Throughout all of this, I’ve realized—as I mentioned last week—the need for me to prioritize where I am putting my time. It’s hard when you’re a small team and are still tied into many of the decisions, both large and small, that need to be made. I discovered a great book called “Essentialism: The Disciplined Pursuit of Less” by Greg McKeown that I’m looking forward to diving into. Have you heard of it?
Best alliance in Hip-Hop
For the past two years, when we are shooting the b-roll (supplemental or alternative footage intercut with the main shot) for our outfit videos, I’ve always put on the same exact playlist—”I Love My 90s Hip-Hop” (Rap music from the golden era). For me, it sets the right vibe and keeps me going, which is important when you’re doing the same five shots over and over and over again. Rob, who is a dedicated Phish fan, humors me. Though Robin, who has heard the same playlist through the floor for two years, has gently requested that I switch it up…
To be honest, after two years, I’ve been getting a little—I wouldn’t say quite sick of it as well, but, you know, a change of pace wouldn’t be the worst thing ever. I do like hip-hop for doing these shoots though.
So recently, I’ve gone back to one particular album, which is just so amazing. A classic in every sense—the eponymous Black Star with Mos Def and Talib Kweli.
Every track is just so good. So. Good. I mean, Kweli makes not one, but two references to John Coltrane—”I love rocking tracks like John Coltrane love Naima” (“Astronomy (8th Light)); “It's how it seems, you make me wanna ride the Coltrane to A Love Supreme” (“Brown Skin Lady”). Come on!
Just because…
I’m going to leave you this week with a great photo of all-time HSS icons Nick and Nora. Could this be the inspiration for next year’s Christmas card? I’m going to have to get that suit made… I’ve also been digging the way William Powell’s pocket squares are always positioned so nonchalantly.
Stylishly Yours,
Brian
"Rules are for beginners". Yes, you will eventually break them but when I just started out my "journey into menswear" (hate that expression), having something in place that says "do this, and look good" is really helpful.
I do admire how you come up with different video formats often but I also do miss some of your older video types as well! Especially the three looks per watch videos, it's very unique.