Notes from the Head of the Charles
A big weekend for preppies and boat people... (aka me)
This weekend was Head of the Charles, the world’s biggest three-day rowing regatta and the zenith of Boston’s fall. For a few days, the river becomes the place to see-and-be-seen, especially if you have a penchant for prep, Viking-sized men and women, and/or sweater weather. As with so many photogenic events, social media has supercharged the weekend. It’s more crowded, more buzzy, and more branded than ever. It looks great on Instagram. Parking is a nightmare.
HOCR as it’s known (not HOTC, confusingly) has been the highlight of my fall for the last 20 or so years. While this newsletter intends to focus more on gear worn for performance, this felt like one occasion where I might wade (pun intended) into a discussion of fashion trends found on the riverbanks. So much of preppy style has its roots in sporting culture – the polo, the rugby, the henley, even the blazer was born from men messing around in boats – that it feels right to take a look at what is resonating among the rowing set these days.
I doubt I was the only one doing some trend peeping, I’ve heard from a former Abercrombie buyer that they used to make an annual pilgrimage to see how the ur preppies were popping their polos.
Speaking of polos, Vineyard Vines is the apparel sponsor for the Regatta, having taken over the helm (again, pun very much intended) from Brooks Brothers a few years back. Based on the size of their gear tent and the line to get in, their merch is popular among high schoolers and tourists. I find their giant-whale approach to prep seriously obnoxious. They also fly in influencers to cosplay as New Englanders and the whole thing annoys me. (I’ll give them credit for this social content, though, a worthwhile effort to highlight the need for more diversity in the sport.).
HOCR has changed a lot since I started attending in ~2000, and brands have taken notice. I didn’t see all the displays, but noticed lots of teens walking around with Depop-branded totes, a smart piece of targeted marketing by the second-hand retailer.
I thought it might be a fun change of pace to break the fourth wall and share how I dressed for the weekend. My approach is to maximize comfort, play with layering, and showcase school spirit. The goal is to look cool, but not try hard.
I’m starting with Friday’s outfit (top left) because I liked it and I saw rowers that day, so it counts. The top is a vintage sweatshirt I snagged from We Thieves in Somerville along with my belt. What I like about the sweatshirt is it has a raw hem, so it’s easier to tuck into pants than one with a ribbed finish. I wore it on Saturday too. If that sounds intriguing to you, I found similar tops on Ebay, here and here. The jeans are Everlane’s 90’s Cheeky Straight – I’d like some wider-legged ones but these never fail me. I wore New Balance 574s on Friday and Saturday, On Cloud Monsters on Sunday and high socks every day, so I didn’t look old.
Saturday I leaned into autumnal dressing, though it ended up being pretty warm. The brown cords are Old Navy and I sized up for a slouchier fit. I layered a big denim shirt from Rag & Bone over the aforementioned sweatshirt to complete the relaxed preppy look.
Sunday was even warmer, so I channeled Alison Bornstein’s “Surfer Nephew” approach to dressing. I wanted to wear the below vintage Yale Sweater I found at a store in Texas (of all places), but opted for layers (as shown above) instead. The shorts are my favorite Patagonia baggies, which I paired with a big Old Navy button-down under an old Everlane fleece. I finished every look off with my trusty Yale Crew hat, of course. Boola boola.
Speaking of vintage Yale sweatshirts, on the left is one my sister snagged ironically at a store in Harvard Square. Schools have really cracked down on having fun with their branding, which is a shame. Naturally, I spotted lots of college crewnecks along the river. I am particularly a fan of the versions I saw from Brown, Columbia, and Dartmouth with simple big Bs, Cs, and Ds. I guess it’s worth noting here that Sporty & Rich is releasing their Ivy League drop this week.
The warmer temps meant that it wasn’t quite barn jacket weather after all – a great disappointment, I am sure, to everyone looking to show theirs’ off. Still, here are a few looks that caught my eye. (Please forgive the iffy photography, I was snapping on-the-go while steering a stroller.)
My favorite outfit was the one on the top right of the grid – a Blackwatch plaid skirt, denim belted jacket, baseball hat, sneaks, and a weiner dog – exactly the relaxed prep look that defines the Charles best. In addition to college sweatshirts, I spotted lots of rugbies, baseball hats, oversized denim, Salomon XT-6s, and, of course, Adidas sambas. I saw zero boat shoes, which is, actually, shocking.
Quick Thoughts
Things That Drew My Eye or Ire…
NCAA champ and Olympian Parker Valby surprised a lot of people by signing with New Balance this week, instead of her NIL sponsor, Nike. Runner’s World had a lot of good context, including several quotes alluding to the fact that NB has big plans for marketing Valby. Her father Kyle told RW, “There are a couple of huge surprises coming soon. This is a historic deal.”
New Balance has a host of incredibly talented women on their running roster, Sydney McLaughlin-Levrone being their biggest star. Valby – from what I have seen – has a bolder personality, which could make things interesting when it comes to “surprises”.
Of note, the comments on this post from Citius Mag suggest that there’s still little love lost for Nike among a certain segment of the running community despite a recent string of good running marketing (their Chicago Marathon out-of-home advertising and Stairs ad were both on point.)
PYNRS, the Boston-based brand inspired by run crew culture has been on a tear this fall, partnering with Brooks on a pop-up series for the Majors, landing funding from Jaylen Brown, and teaming up with McGarry & Sons on future product design. McGarry & Sons is the team behind some of the best sports apparel on the market. They helped launch Tracksmith’s earliest collections and have worked with Hoka and other major players – though you don’t see their name in the press as much as their track record deserves.
As a lifelong Bostonian and fan of women’s sports, it was a major bummer to see the launch of the city’s new NWSL team name go so awry. The New York Times has all the details on the Bos Nation launch fail but I really would not want to be the creative who thought “Too Many Balls” was the right direction for the campaign.
WSJ’s Rachel Bachman examines the WNBA’s recording-breaking year and Create Cultivate showcased the stylists shaping the tunnel walk. Also, I know I dropped the ball on covering the WNBA championships – cheers to the Liberty! – will work on it for next season.
Forbes profiled hurdler Alaysha Johnson (she of the self-designed kit at Trials). From the story: “I've never ever worn a shoe company kit," she states. "I consciously decided not to promote brands for free." This move was more than a fashion statement; it was a calculated decision to maintain control over her image and brand in an industry where athlete independence is often compromised. Johnson believes that athletes should be fairly compensated for their promotional value, challenging the traditional model of athlete-sponsor relationships and suggesting a future where athletes have more control over their personal brands.”
Very into this jersey collab.
I’ve got some amazing interviews on deck and am excited to dive into skiwear in the coming weeks. Let me know how you liked this foray into sharing a little more of my own style. I don’t plan on doing it often, but it could be fun to do some vintage shopping round-ups, if there’s interest.
Best one yet for us New Englanders