February 2nd, 2026
Wore this out to dinner with my wife, mb. My hair is chaotic because I was still a bit sad about a hard conversation I’d had to have with a friend a couple days before this, but mb took good care of me! Anyone remember this old Dildorks logo, drawn by Amy/Starboots? I still love it, even though we don’t really look like this anymore and have since switched to new album art by Addison Finch.
What I’m wearing:
- Dildorks baseball tee – Zazzle circa 2017
- Black cashmere cardigan – Gap
- Black ponte pants – Gap, gift from my mama
- Black leather Frye harness boots
- Black leather vintage Coach Willis bag
February 4th, 2026
It was insanely cold in New York for much of January and February – and I say that as someone who grew up in Canada! I bundled up every time I left the house, and also had to layer my clothing carefully, even for quick jaunts to the local pizzeria or dispensary.
Here’s what I wore to go have drinks with my pal Brent (a.k.a. Brentalfloss, my Question Box cohost) at a bowling-themed bar called Gutter Bar. We regaled each other with various gossipy sagas from our personal and professional lives over IPAs. Pretty ideal, despite it being so cold outside that my eyelashes kept freezing over when I was en route!
What I’m wearing:
- Pink cashmere sweater – J. Crew
- Denim jumpsuit – Aritzia
- Pink knit toque – gift from my mom
- Pink leather Doc Martens
- Prescription sunglasses – Zenni
- Black leather vintage Coach Willis bag
- Navy clitoris-shaped earrings – a now-defunct Etsy shop
February 6th, 2026
It’s always a good day (or night) to visit Boyfriend Co-Op, a lesbian bar/café overflowing with vintage furniture and mellow vibes. Went there with my wife on this day to celebrate some good news she’d received! We sat at the bar and sipped lovely cocktails over great conversation.
What I’m wearing:
- Blue “Slut for Kindness” T-shirt – Supriya x Eva Bloom
- Blue cashmere cardigan – Gap
- Skinny jeans – thrifted
- Blue metallic Doc Martens
- Black knit toque with ghost logo – Vaultboy merch
- Black leather vintage Coach Willis bag
February 7th, 2026
Another outfit for a low-key dinner with the wife, if I recall correctly. We may have been going to Santa Panza. (Their ragu mafaldine pasta is my favorite comfort meal currently. Preferably with a Paper Plane or two!)
What I’m wearing:
- Black blazer – thrifted
- Red T-shirt – thrifted
- Black pants – Gap, via my mom
- Black leather Frye harness boots
- Silver hoop earrings
February 8th, 2026
Another way-too-cold day. One thing I learned, growing up in Toronto (and occasionally having to schlep to 8 a.m. university lectures on the streetcar in the middle of winter), is that comfort is ultimately more important to me than looking cute. It sucks when you’re trying to have a good time with pals but you can’t stay present because your teeth are chattering and your knees are knocking together! I still aim to strike a balance between coziness and cuteness, as seen here – but when push comes to shove, practicality has to win out, ’cause you know what’s not cute? Frostbite!!
What I’m wearing:
- Black cashmere Ralph Lauren sweaterdress – a hand-me-down from my high school girlfriend circa 2009
- Black modal nightgown (layered underneath, for warmth & coverage) – Calvin Klein Sleepwear
- Black woollen tights
- Black leather Frye harness boots
- Black leather vintage Coach Willis bag
- Navy clitoris-shaped earrings
…and incase you were wondering what it looked like when I went out:
…Here’s a bonus outerwear shot of the same outfit! Additions include:
- Bright turquoise long goosedown coat – bought from Land’s End several years ago; my friend Casia once told me that this makes me look like I’m wearing a sleeping bag, but it is extremely warm, so it’s worth it!
- Navy knit cowl – Yokoo (absolutely obsessed, big recommend, it is one of the main things getting me through this winter)
- Black knit toque with ghost logo – Vaultboy merch
February 10th, 2026
mb and I were celebrating our 8-year collarversary, i.e. 8 years since she first put a collar on me! Our collars have always been blue because it’s a special color in our relationship history, so I always wear blue to celebrate this day.
It was a perfect date night: first, mb took me to dinner at Le Crocodile, the French restaurant in the lobby of the Wythe Hotel, which is where we were staying together when she first collared me. I didn’t realize that’s where we were going, and I practically burst into tears when we got there! Then we went to see the Improvised Shakespeare Company perform. They were transcendent; I laughed so hard I couldn’t breathe. Improv is also very romantic for me and mb, because we’ve both always loved it and we saw some New York improv together on our second date, way back in 2018 💙 Thanks to mb for planning such a beautiful evening for us!
What I’m wearing:
- Blue crushed velvet dress – Forever 21, many years ago; bought to wear to our first collarversary date, if I recall correctly!
- Blue cashmere cardigan – Gap
- Black leggings – Gap
- Blue metallic Doc Martens
- Tiffany & Co. dog collar – a gift from my love
- …& barely visible: a great Agent Provocateur bra, because sometimes cleavage can pull a whole look together 😉
February 13th, 2026
Another wonderful date night with da wifey: we had pizza at Roberta’s and then watched Sinners, which was fantastic. At the pizzeria, they were having a “My Bloody Valentine”-themed party, so lots of the servers had fake blood spattered all over them (which might’ve been marinara sauce, for all I know), and a tattoo artist was doing Valentine-y flash tattoos in the back room. I love Brooklyn.
What I’m wearing:
- Magic Wand T-shirt – Pen & Kink
- Black flared jeans – Gap
- Black leather Frye harness boots
- Black leather vintage Coach Willis bag
- New red prescription glasses – Zenni
February 14th, 2026
Valentine’s Day outfit! Y’all know I love to dress in a Valentine-y manner and will take any excuse to do so, so I had fun putting this look together, as ever. I had also just received a new push-up bra in the mail from Victoria’s Secret, which was fortuitous timing 😂
What I’m wearing:
- Red tank top – gift from my mama
- Red pencil skirt – American Apparel like a decade ago
- Black leggings – Gap
- Red cowboy boots with stars on them – a hand-me-down from my high school girlfriend’s mom in 2008 or so
- Red suit jacket – borrowed from my wife; it’s part of a suit she had custom-made by Alan David to officiate a wedding (I wish the pants fit me too, ’cause I would’ve just worn the whole suit instead!)
What clothes/outfits have you been loving lately, my darlings?
