
April 8th, 2026
So I bought a red leather motorcycle jacket. Like so many of my best decisions, my wife had to talk me into it. An email showed up in my inbox declaring that a bunch of Danier Leather stuff was on sale, including their classic motorcycle jacket in “radiant red.” I already have a leather jacket that I love (incidentally also by Danier), but it’s black, so it doesn’t exactly stand out – and its shape is plain and boxy, lacking the effortless cool of a moto-style jacket. After some hemming and hawing, I pulled the trigger, and it arrived in my eager little hands a few days later.
This was the jacket’s maiden voyage – I wore it to attend an improv show at Comedy Bar. I felt nervous at first, like I wasn’t quite “pulling it off” – but pretty quickly, the jacket’s magic started to rub off on me, giving me some confident swagger I normally find hard to access. The intersection of clothing, gender, and confidence is so fuckin’ rad, dude. And funnily enough, none of my friends at the bar even commented on the jacket the first time I wore it, which I took to be a sign that it didn’t look out-of-place on me at all!
What I’m wearing:
- Red leather jacket – Danier Leather (spoiler alert: you’re gonna see it a lot in this post! Like, in every outfit!)
- Dark red tank top – gift from my mom
- Black straight-leg jeans – Gap
- Custom-color Nike Air Force 1 sneakers
- Vintage red leather Coach Willis bag – Etsy
- Prescription sunglasses – Zenni

April 10th, 2026
A fun solo date night! I love taking myself out for little adventures around the city. First I went to Comedy Bar (yep, again… it’s my home-away-from-home-away-from-home, okay?!) and drafted some song lyrics over a beer. Then I subwayed over to Casa Sushi for dinner, where I hadn’t been in ages, although it was one of my major haunts in my early twenties. Then I had some time to kill before an IMAX screening of Project Hail Mary (absolutely loved it), so I had a drink at the very swanky Stock Bar, journaling in between two couples on dates. Vaped a little weed before heading into the movie theatre; highly recommended for any space movie, as long as you’re not too prone to anxiety!
What I’m wearing:
- Red leather jacket – Danier Leather
- Hot pink sweater – Gap, gift from my mom
- Blue skinny jeans – thrifted
- Custom-color Nike Air Force 1s
- Vintage red leather Coach Willis bag
- “Ace” baseball hat – from the Ace Hotel shop; a gift from mb, picked out by pax; I love that it inadvertently advertises part of my sexual identity 😂
- Prescription sunglasses – Zenni

April 14th, 2026
Hello, Chicago! After my wife gave a delightful and widely acclaimed keynote talk at Deep Dish Swift, the two of us met up with her friends Alex and Jillian for dinner at Monteverde, which was delicious. Fun night! I may have had a few too many Paper Planes…
What I’m wearing:
- Red leather jacket – Danier Leather
- Blue tank top – thrifted
- Black straight-leg jeans – Gap
- Black leather Frye harness boots

April 15th, 2026
Another nice day in Chicago! We visited the Bean and a vintage camera shop, and later went out for dinner (+ excellent ice cream from Jeni’s) with mb’s friends Syd and Quinn. Then we zipped across town to the Annoyance Theatre to see their jury duty-themed improv show, which was a blast.
What I’m wearing:
- White T-shirt with vintage Apple logo – gift from mb
- Black cashmere cardigan – Gap
- Black straight-leg jeans – Gap
- Black leather Frye harness boots
- Red leather jacket – Danier Leather
- Little red leather purse – came with a gift from Clarins

April 16th, 2026
I’ve been highly enamored with Field Notes pocket notebooks lately, so I wanted to visit their HQ while we were in town. It’s only open to the public a few days of the week. Such a chill space, filled with notebooks and nerds thereof! I admittedly left with 7 more notebooks than I’d had when I walked in…
What I’m wearing:
- Red leather jacket – Danier Leather
- Red tank top – Gap
- Black straight-leg jeans – Gap
- Black leather Frye harness boots
- Red leather bag – Clarins
- The key to my sub’s chastity cage worn on a necklace
- Prescription glasses + sunglasses – both from Zenni

April 17th, 2026
I got back to Toronto in time to attend the monthly free karaoke night at Comedy Bar, where I was celebrating my early birthday with some friends (my actual birthday is the 23rd). Had a great time, laughed my ass off, sang some Sondheim, drank a lot of beers, etc.!
What I’m wearing:
- Red leather jacket – Danier Leather
- Red fit-and-flare dress – H&M
- Black leggings – Gap
- Custom-color Nike AF1s
- Red leather vintage Coach Willis bag
How would you style a red leather jacket? Feel free to let me know in the comments…
P.S. Want more blog posts like this? Check the outfit tag!









