October 4th 2026
Worn to a Studio Sundays, the weekly musical improv show/jam at Comedy Bar which is a fixture of my week whenever I’m in Toronto. Always a hoot! On this night I sipped an old fashioned, had so much fun in the improv jam, and then got walked home by two of my favorite sweet comedy boys. Do ya like my polka-dot motif?
What I’m wearing:
- Navy polka-dotted dress – H&M (last year I wore this dress the night that I got painfully rejected by a crush, and so I regarded it as cursed for a while, but I’ve been trying to reclaim it!)
- Blue cashmere cardigan – J. Crew
- Navy polka-dotted socks – gift from my mom I think
- Black suede Minnetonka moccasins – bought when I was 22 (in 2014!!) and recently rediscovered in my closet at my parents’ house; I recall that I bought these with money I made when a bride and groom commissioned me to record a version of the Magnetic Fields song “It’s Only Time” so they could do their first dance to it!
- Vintage red leather Coach Willis bag
- My wife’s chastity key on a silver chain (happy Locktober! – it’s tucked under my dress in this case, for modesty’s sake)
October 13th 2026 (daytime)
Wore this to a coffee/breakfast hangout with my wife and her girlfriend at our local lesbian bar/café. (What a Bushwick-ass sentence, huh?)
What I’m wearing:
- Black T-shirt – accidentally stole from an unknown neighbor when it got mixed in with my laundry
- Green & blue plaid flannel shirt – Old Navy (I always feel my gayest in a flannel, don’t you?)
- Denim shorts – the Gap
- Black thigh-high striped socks – American Apparel
- Blue metallic Doc Martens
- Vintage black leather Coach Station bag
- Prescription sunglasses – Zenni
October 13th 2026 (nighttime)
Changed into this outfit in the evening for a pizza date with my cute boyfriend. I always feel kinda weird about wearing red and blue together, lest my look be construed as some kind of “patriotic” statement in an era when living in the U.S.A. isn’t exactly a brag… but I think this is cute!
What I’m wearing:
- Red fit-&-flare dress – H&M
- Blue cashmere cardigan – J. Crew
- Red leather jacket – Danier Leather (yep, still obsessed)
- Red Christmas socks – gift from my mom
- Blue metallic Doc Martens
October 14th 2026
Here’s what I wore to go see hilarious improv boys Chicken Big perform at the Brooklyn Comedy Collective – they always leave me screeching with laughter! This is definitely my favorite outfit in this whole post. Sometimes I truly do want to get rid of all my clothes that aren’t pink and red, and just commit to a fully “lovecore” wardrobe… but I think ultimately I love blue, green, and yellow too much to ever give them up!
What I’m wearing:
- Pink cropped T-shirt – the Gap
- Red “Sloan” pants from Banana Republic – thrifted recently (I already loved the look of them before I saw that I share a name with this style of pant, at which point I decided they were clearly destined to be mine!)
- Pink Doc Martens
- Red leather jacket – Danier Leather
- Black prescription sunglasses
- Black leather vintage Coach Station bag
October 16th 2026
Return of the Sloan pants! Gosh I love these. They’re such a statement. Worth noting, too: this month I did a lot of foot fetish play with partners, as a top (i.e. the person whose feet are being worshipped), and so I found myself wanting to wear heels and sandals a lot more often, because I had foot stuff on the brain. Always love an opportunity to wear these cute red clogs!
Choosing an outfit for this night was a fun challenge, because the plan was dinner at the very fancy Union Square Café, followed by two improv shows at the Upright Citizens Brigade theatre. I felt neither overdressed nor underdressed at either location, which was ideal.
What I’m wearing:
- “Sex, love, & disco” tank top – was recently gifted to me in a press mailer for a collaboration collection between sex toy brand Womanizer and celebrity crystal designer Disco Daddy
- Red “Sloan” pants – thrifted
- Red peeptoe heeled clogs – Lotta from Stockholm
- Red leather jacket – Danier Leather
- Black leather vintage Coach Station bag
- Black prescription sunglasses
October 17th 2026
My mom came to visit New York for her birthday, and took me to Billy Crystal’s latest one-man show on Broadway, 860, which is about losing his family home of 46 years to the devastating L.A. wildfires. We had a delicious dinner with my wife before the show, and then I sipped champagne with my mom in her hotel room after the show. A lovely night!
What I’m wearing:
- Black cashmere J. Crew sweaterdress – hand-me-down from a high school girlfriend
- Pink silk slip (underneath) – vintage on Etsy
- Black leggings – H&M
- Pink Doc Martens
- Red leather jacket – Danier Leather
- Pink sparkly heart necklace – Tarina Tarantino
October 19th 2026
Here’s what mb and I wore to an Improvised Shakespeare Company show. Highly recommend seeing those gents perform if you ever get the opportunity – I don’t know how they do what they do, but it’s astonishing to watch! Also, doesn’t mb look amazing?! Her outfit reminded me of Carmen Sandiego.
What I’m wearing:
- “Fucking Fascists” T-shirt – gift from my mom maybe?
- Red “Sloan” pants again
- Black cashmere cardigan – the Gap
- Black Doc Martens
- Red leather jacket – Danier Leather
- Red knit cowl – Etsy seller Keely Devine
- Black leather vintage Coach Station bag
October 22nd 2026
Another fun outfit challenge: mb and I first went to dinner at Diner, so I wanted to dress somewhat fancy/sophisticated for that, but then our plan was to part ways and each go see a movie – she was seeing The Devils and I was seeing the 3-hour-long You Can See Everything, and I was in the midst of a chronic pain flare-up, so I needed my outfit to also be as comfortable as possible. I was happy with what I came up with, and it served me well all evening; this modal nightgown, in particular, feels as light as air on my skin.
What I’m wearing:
- Men’s black T-shirt
- Long red modal nightgown – Calvin Klein Sleepwear
- Dark red thigh-high socks – Los Angeles Apparel
- Black cashmere cardigan – the Gap
- Black leather Chuck Taylor sneakers
- Red leather jacket – Danier Leather
- Red knit cowl – Keely Devine
- Pearl necklace – gift from my wife
- Yellow leather bag – Kate Spade
October 23rd 2026
Very similar to the previous day’s outfit, because I was once again dressing for comfort – I’d gotten my flu shot and COVID shot the day before, which always makes my chronic illness symptoms flare up real bad for a few days. My wonderful boyfriend, knowing that I wasn’t feeling well, suggested we have our date night at Mile End, a Montreal-inspired deli in Brooklyn that makes many of my favorite Canadian and/or Jewish comfort foods, like matzoh ball soup, potato latkes, and Nanaimo bars. It was absolutely what the doctor ordered!
What I’m wearing:
- Dark red wide-legged modal jumpsuit – MeUndies (modal remains the easiest material for my body to tolerate in the midst of a flare-up)
- Black leather Chuck Taylors
- Red leather jacket – Danier Leather
- Red knit cowl – Keely Devine
- Black leather vintage Coach Station bag
October 27th 2026
Worn to a Rocky Horror screening with some pals. It was super fun to see this queer classic with some friends who’d seen it before and some who hadn’t! Had to bust out heels and pearls for this one, natch…
What I’m wearing:
- Red T-shirt – thrifted
- Red pencil skirt – American Apparel
- Black cashmere cardigan – the Gap
- Black tights
- Black leather Naturalizer Izzy sandals – a findom gift from my wife 🤑 (surprisingly comfy!)
- Pearl necklace – also a gift from my wife
- Red leather jacket – Danier Leather
- Red leather vintage Coach Willis bag
November 1st 2026
One of my closest pals was performing as part of a longform musical improv troupe; here’s what I wore to go watch her shine! The show was completely sold out and she knocked it out of the park, as ever.
What I’m wearing:
- Red spaghetti-strap chemise – American Apparel many years ago, just rediscovered in my closet
- Red & black plaid flannel shirt – thrifted; brand is Uniqlo
- Black leggings – American Apparel
- Black Doc Martens
- Red leather jacket – Danier Leather
- Silver hoop earrings
- My wife’s chastity key on a chain
- Vintage red leather Coach Willis bag
