Okay, so I decided I needed a new cap. My old trusty one, you know, the classic New Yorker style, finally bit the dust after years of abuse. Looked online, saw the prices for official stuff, and thought, nah, I can probably make something myself, right? How hard could it be? Famous last words.

First step, I grabbed a plain, dark blue baseball cap. Found one cheap online, decent quality, blank canvas. Perfect, I thought. My grand plan was to do some cool, custom embroidery. Maybe a stylized ‘NY’, something simple but sharp.
Getting Started (or Trying To)
So, I got my cap, some embroidery floss – picked white for that classic contrast – and a pack of needles. Spread everything out on the kitchen table. Felt pretty good, ready to craft.
First hurdle: getting the design onto the cap. I sketched a simple ‘NY’ on paper, looked okay. Tried drawing it directly on the cap with a pencil. Barely visible. Tried chalk. Rubbed off instantly. Ugh. Found some old tracing paper, printed the logo, and painstakingly tried to transfer it. It kinda worked, left a faint outline. Good enough, I figured.
The Actual Stitching… or Stabbing
Needle threaded, ready to go. I punched the needle through the cap fabric. Wow. This stuff was tougher than I thought. It wasn’t like stitching a patch onto a jacket. This was thick, structured material. My fingers already started complaining after the first few stitches.
And the look? Terrible. My stitches were uneven, clumsy. The thread kept looping weirdly. It looked nothing like the neat, professional embroidery you see. It looked like… well, like someone who didn’t know what they were doing was stabbing a hat with thread. Which was accurate.

- The needle felt too thick, or maybe too dull?
- The floss tangled if I pulled too fast.
- Keeping the tension right was a nightmare.
- My fingers were getting sore. Seriously sore.
I spent maybe an hour getting about half of the ‘N’ done, and it looked awful. Like, really bad. I got frustrated. All those online videos make it look so smooth and easy. Liars! It’s never that simple, is it? Reminds me of how companies talk about their shiny tech stacks, but under the hood, it’s often just duct tape and wishful thinking holding things together.
Switching Gears
I almost threw the hat across the room. Took a break. Stared at the sad, half-finished ‘N’. This wasn’t working. Embroidery on this specific cap, with my non-existent skills, was a bust. Time for Plan B.
Remembered I had some fabric paint markers stashed away from another project I abandoned (seeing a pattern here?). Dug them out. Okay, maybe not as “classy” as embroidery, but way easier. Sometimes you just gotta pick the tool that gets the job done, even if it’s not the one you originally planned for. Pragmatism over purity, I guess.
So, I carefully went over the faint outline I’d traced earlier with a white fabric marker. It flowed reasonably well. Had to do a couple of coats to get it opaque. It wasn’t perfect embroidery-level crispness, but it was clean, it was white, and it looked like an ‘NY’. I even added a couple of small personal marks on the side, just little dots, to make it truly mine.
The Finished (?) Product
Let it dry overnight. Woke up, looked at it. Yeah, it’s clearly homemade. The lines aren’t laser-perfect, and up close you can tell it’s marker, not thread. But you know what? I kinda liked it. It’s got personality. It’s my version of a New Yorker hat. It carries the memory of my failed embroidery attempt and the pivot to paint.

Wore it out. Felt pretty good. It’s comfortable, it’s unique, and it didn’t cost me a fortune. Plus, I learned something – mainly that I suck at embroidery on thick caps, and sometimes Plan B is the way to go. The whole process was a bit messy, a bit frustrating, but the end result works for me. And isn’t that what most projects are like, really?