You’re reading Oak Drive’s Monthly Update — a newsletter about me and my brother building a clothing brand from scratch. Each issue shares honest updates, real thoughts, and the actual numbers behind creating something high-quality and sustainable.
No playbook. No overnight success. Just two brothers trying to do it right — one misstep at a time.
Let’s get into it.
— Nick
TL;DR
🧢 Hat reality check: 4 styles → basically down to the Dad Hat (camo shelved)
🪖 Camo hat: polls were meh + accidental political vibes → on ice (Johnny still loves his 1-of-1)
✅ Dad hat: monochrome version finally nailed → ready for inventory + production
👕 Tees in Peru: 2nd sample just arrived; collar/color still unclear → approve now vs sample again
👩🦰 Unisex/women’s push: strong demand → considering a women’s cut + positioning Dad Hat as truly unisex
📱 Marketing truth: product isn’t the problem — no content = no audience → TikTok push starts in December
We’re late… Again 🫠⌛
Not because we weren’t working, although admittedly it feels like we haven’t accomplished much…I blame Thanksgiving and Mal putting me on too many house projects.
Here’s a little foreshadowing for you: TikTok remains undefeated
Anyway. Welcome to November.
Hat Updates: Darwinism, Pantone, and Political Side-Eye
When we started the hat project, we had ambition. Four styles:
Wool
Navy USA
Camo
Dad Hat
We are now down to two:
The Camo Hat
CC (Nick’s girlfriend) hates the camo although she hasn’t actually told me that to my face…I just have heard it through the Nick-shaped grapevine. I argued, and like most things in Nick’s romantic life, she won.
As a market test, I ran a poll with my friends and while a few people swore they’d buy it, general sentiment was that “it’s fine.” … not a resounding “YES I WOULD LOVE TO BUY IT”
Which brings me to the most glaring problem with the hat.
Somehow—without even trying—the creative genius of our camo hat got misconstrued and drifted into political territory. Turns out the beloved 2nd place runner up to President Donald Trump, Harris/Walz, had a very similar idea as I did. I have to think it was to grab the “Minnesotan” vote (not sure why they were worried about that, they had much bigger fish to fry), but considering I had never seen the hat until I was told about it, I don’t think it landed well with consumers in Gov. Walz home state.
Long story short, I still absolutely LOVE the hat, but I am not stupid (or prideful) enough to not listen to our consumers. The camo hat design is on the shelf to collect dust.
As a consolation prize, I did workup the perfect sample and have a 1-of-a-kind Oak Drive camo hat sitting in my closet.
The Dad Hat: We Finally Nailed It
We’re proud of this one. It just took a while…
The progression:
Black and white patch → looked awful honestly don’t know who looked at this and thought to themselves… Oh that’ll do.
Change to a woven patch with black border → Still not right but much better
Next step Beige + navy → better, still busy
Monochrome → finally right
It’s clean. Subtle and kind of sneaky refined. Oh, and also unisex.
We’re ready to pull the trigger on inventory and move this thing into production; a sentence we’ve been chasing for months.
👕 Shirt Update
Quick reminder of where we left off:
Manufacturing is in Peru
MOQ is 200 per color
Target colors: black, white, gray, navy
Fabric is elite
Nick, mainly, has been working with our POC in Peru to get most of this done. We got our first sample, which was great. We only had a few revisions:
Make the body and the sleeve length just a bit shorter
Update the collar to be more like one we like from Buck Mason
It takes a shockingly long amount of time to turn revisions, get the shirt cut, sewn, sampled and shipped.
Nick just today got in the second sample, but since the fabric of the body and collar are different, it’s oddly hard to tell if we like it.
We’ve got two option:
1. Decide we love the shirt material and cut, despite not seeing the true color
2. Sample again and kick things back another month or so
A Quiet Announcement: Women Like to Buy Clothes
Breaking news: Women LOVE to buy things
Mal, CC and pretty much every woman we’ve ever spoken to have informed us that we need to make women’s clothing. Or at minimum, unisex offerings.
Fair.
We’re actively talking about producing a women’s cut of the shirt—same quality, different shape—and leaning further into the dad hat as a truly unisex product.
Oak Drive doesn’t grow without women buying it.
So we’re listening.
Just don’t hold your breath. If there’s one thing that we’ve learned its that new things take time.
📞 Momentum, Dopamine, and My Fight with Social Media
I promised a singular TikTok post in our October newsletter and I didn’t even come close to accomplishing that. I seem to find every excuse in the book not to post.
At first, it was more so about what others would think of my brutal content, but I am so over that. It’s truly just something I loathe. I don’t know if it’s because I truly don’t like it, or just hate doing things that I suck at…only one way to find out.
I vow to be better. I will post on TikTok before you hear from me next.
Doubtful… -Nick
▶ Song on repeat: Dancing in the Moolight - King Harvest
▶ Current read: Careless People
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