I first started wearing liquid eyeliner in the eighth grade. I tried it on when I dressed as Marilyn Monroe for Halloween one year and promptly fell in love.
The problem is, liquid eyeliner is a fickle mistress. My initial go-to was by L’Oreal and would sting horribly any time it got into my eyes – which was almost inevitable, because it would smear any time I cried, and I’m a very tears-prone person. Later I tried other liquid eyeliners, by Stila, Kat Von D, and Urban Decay – but all gave me some version of the same problem: they would smudge if I cried at all, or even if I laughed too hard. Given the type of life I lead, that shit just wasn’t gonna fly!
But all such problems went away when I tried MAC Liquidlast liner for the first time. Now it’s been my liquid liner of choice for over 6 years. Every time I branch out and try a different one, I end up regretting it and going back to Liquidlast. Monogamy isn’t my jam when it comes to relationships, but in the realm of eyeliners, there’s only one true love for me! 😂
A few key scenarios where Liquidlast has consistently out-performed the competition:
Crying: As mentioned above, I cry a lot – sad tears, happy tears, occasional “what the fuck?!” tears – and have never found an eyeliner that stands up to it better than Liquidlast. At most, I’ll get some minor flaking that’s easily solved with a quick touch-up.
Laughing: I am a very expressive laugher, prone to cackling so hard that my eyes squeeze shut – so getting femmed up to attend comedy shows was always a dicey proposition for me before discovering Liquidlast. Now, I have no such worries, not even when I’m seated in the front row of an improv set featuring performers I think are total babes…!
Rain: When the skies crack open and start pouring on me while I’m en route to a date or a show, I’m never concerned that my eyeliner will run. Other stuff might (concealer, blush, mascara), but Liquidlast does not give a fuck. It laughs in the face of rainfall.
Sweat: I am a sweaty person at times, whether it’s prompted by vigorous sex, hot-and-heavy makeouts, or just power-walking the streets of Toronto or New York, and Liquidlast handles it without issue.
Blindfolds: Wearing a blindfold during sex/kink is a pretty frequent thing for me, and my Liquidlast is always intact after such a session, save for maybe some slight flaking.
Naps: I am a medically tired person and have been known to take li’l disco naps before big nights out – and amazingly enough, when I use my fave tried-and-true longwear products like Liquidlast, I can nap on a fully-done face without fear of fucking it up. Occasionally I might need to fix a lip smear or touch up some flaked-off spots, but mostly it looks just fine.
Stage performance: Not only does Liquidlast hold its own against stage-fright sweat – it actually looks blacker than a lot of other eyeliners, even under stage lights. Great for my occasional improv & music performances!
Giving head: My decade-old blog post on blowjob-friendly lipsticks is still one of my most-viewed pages, so I feel it’s important to tell you that Liquidlast lasts longer than anyone I’ve ever blown. 😉 As a sexually anxious person, it honestly helps me a lot to know that my eyeliner will still look on-point afterward even if I get cum/drool/sweat all over my face.
Fellow makeup-lovers, do you have an eyeliner you treasure as much as I treasure MAC Liquidlast? Feel free to tell me about it in the comments!
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
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!
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.
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!
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.
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?
I flew back to New York from Toronto the day before this, and usually air travel is pretty draining for my chronically ill bod, but fortunately I had enough energy to go out to Raaaatscraps! My wife and I had also just watched an amazing video about beef wellington that inspired her to seek out a great wellington at a restaurant, so that’s what we had for dinner before the show. A cute date night!
What I’m wearing:
Pink cashmere sweater – had just received as a Christmas gift from my mama 💖
Black pants – ditto
Black T-shirt with Apple logo (unseen) – gift from my wife
Pink leather Doc Martens
Silver hoop earrings
Coach Rambler bag
December 30th, 2025
My lovely wife mb was celebrating a birthday, and asked that everybody dress monochromatically for her party. I considered wearing all blue or all pink, but ultimately red won out! The party took place in the “red room” at Singers, so I matched the decor. 💅 Such a fun night hanging out with cool folks! Happy birthday, mb!
Wore this to a New Year’s Eve party! Thanks to Twig, Carly, & Tom for once again hosting; I’ve been to their parties for several years running and always have a good time.
What I’m wearing:
Black & silver body-con dress – vintage American Apparel, bought on eBay
Black tights
Black sequinned Uggs
Vintage black leather Coach Willis bag
Red heart necklace – Tarina Tarantino
Apple Watch
Silver hoop earrings
January 2nd, 2026
Not the most exciting day – I just went out for coffee, cranked out three blog posts, and then watched a really good rom-com. But this denim jumpsuit makes me feel gay and hot on even the most humdrum of days.
What I’m wearing:
Short-sleeved denim jumpsuit – Aritzia; still wish I’d bought the black one too 😭
Black leather Frye harness boots
Black knit toque w/ blue ghost appliqué – Vaultboy merch (his latest EP is wonderful, especially this song)
Navy knit cowl – Yokoo (cannot recommend their knitwear highly enough; this beautifully voluminous scarf has been getting me through this bitter winter, and incidentally works well as a makeshift pillow on uncomfortable chairs!)
Black wool peacoat – thrifted in 2007
Apple Watch
Prescription sunglasses – Zenni
January 10th, 2026
Wore this out to a little drinks get-together with my polycule. Had some great cocktails and funny conversations with a buncha cuties! (And yes, I did also cry on my metamour while making out with him, but that’s neither here nor there…)
What I’m wearing:
Navy skater dress – American Apparel
Black tights
Black leather Frye harness boots
Silver hoop earrings
Teal leather collar – Tiffany’s, a gift from my love
Apple Watch
January 14th, 2026
Wore this to attend an improv show with my wife that featured Aaron Jackson, Josh Sharp, and Jeff Hiller, all of whom are hilarious beyond reason. It ended up being kind of dramatic because there was a subway train shutdown right before the show and Jeff was on that specific train, along with several audience members – so the show started half an hour late, and Jeff ran onstage triumphantly to thunderous applause when they finally arrived after their ordeal. The ensuing set was manic in the best way!
What I’m wearing:
Turquoise long-sleeved shirt – gift from my mom
Black pants – ditto
Blue metallic Doc Martens – bought in high school
Silver hoop earrings
Apple Watch
Vintage black leather Coach Willis bag
January 18th, 2026
Another Raaaatscraps night! You know it’s a really good improv show when you’ll willingly trek over there in bitterly cold weather just to laugh the night away. This particular show is always worth the journey!
What I’m wearing:
Pink cashmere sweater – J. Crew
Black pants – gift from my mom
Pink leather Doc Martens
Red knit cowl – a now-defunct Etsy shop
January 20th, 2026
Kind of a chaotic/mismatched outfit, vibes-wise, but sometimes that’s fun. I wore this out to dinner at Gage & Tollner with my wife.
What I’m wearing:
Red plaid flannel shirt – Old Navy
“Fucking Fascists” T-shirt with rainbow logo – not sure, possibly a gift from mb?
Red pencil skirt – American Apparel
Black tights
Black leather Frye harness boots
Vintage black leather Coach Willis bag
Black prescription sunglasses
January 22nd, 2026
Wore this to a Poetry is Gay reading, at which my stunning wife performed some poems. Always so much fun to listen to beautiful queers reciting their beautiful words! The theme of the evening was “melt the ice,” so I dressed in a springy manner to hopefully hasten along warmer weather (and fewer federal goons on the streets of Minneapolis and elsewhere). 🤞
What I’m wearing:
Floral-print T-shirt – American Apparel
Red pencil skirt – American Apparel
Black cashmere sweater – Gap
Black tights
Red cowboy boots – hand-me-down
Orange & red beaded earrings – bought in Mexico many years ago
January 23rd, 2026
And here’s one silly loungewear outfit, for good measure… I wore this to lie around the house reading my press galley copy of Rosa Campbell’s forthcoming book about the sex researcher Shere Hite. It’s an absolutely fascinating book; big recommend for anyone who’s interested in the intersections of feminism and sexuality, which I’d imagine is most of you reading this blog!
If I look a little frazzled in these photos, it’s because I’d been out late on a great date the night before… but it’s also because I desperately needed a haircut! Went to see the wonderful Carlin, who fixed me right up.
I’d recently attended a party at a bar where Jenna Marbles videos were inexplicably being projected onto one wall, and when my metamour asked the bar if they could turn it off, they instead just changed it to a documentary about GG Allin… which inspired me to dig out this T-shirt that bears his name alongside some Dr. Seuss parody art.
What I’m wearing: • “Gonna fuck this ham” T-shirt – the Black Market several years ago; I cut off the neckline and sleeves in a nonconformist delirium
• Jeans – thrifted
• Black leather jacket – Danier Leather
• Black leather Frye harness boots
• Vintage black leather Coach Station bag – bought on eBay circa 2012
October 10th, 2025
On Bluesky I described this outfit as a mix between Courtney Love and Violet Beauregarde – in the sense that it’s a classic Courtney dress+boots combo, but all in Violet’s signature color! Wore this out to a fancy sushi dinner with my wife, after having interviewed the delightful Tuck Woodstock together for a podcast episode earlier that day.
What I’m wearing:
• Pale blue tennis dress – bought from some random Amazon store for my Magic Wand event at the Museum of Sex back in 2024 (I love that it has a built-in bra and shorts underneath)
• Blue cashmere cardigan – the Gap
• Blue metallic Doc Martens – bought when I was in high school
• Vintage red leather Coach Willis bag – a vintage shop on Etsy
October 11th, 2025
Wore this to go see a screening of All About Eve (which I had never seen before and which absolutely rules) with someone I affectionately refer to as my Movieboy. We went out to dinner first and I had an espresso martini, so I was exactly the right amount of fired-up to see a movie about messy actresses betraying each other!
What I’m wearing:
• Red T-shirt – thrifted
• Blue cashmere cardigan – the Gap
• Black ponte pants – the Gap
• Black leather jacket – Danier Leather
• Custom-color Nike Air Force 1 sneakers
• Vintage red leather Coach Willis bag
October 12th, 2025
A pretty simple outfit, worn to dinner + a Raaaatscraps show, which is the usual Sunday-night tradition my wife and I stick to when I’m in New York. Comedy date nights are the best date nights, if you ask me.
What I’m wearing:
• Black A-line dress – H&M
• Black and white star-print cardigan – ASOS many years ago
• Black leather Frye harness boots
• Vintage red leather Coach Willis bag
• Turquoise leather Tiffany’s dog collar – a gift from my love
October 19th, 2025
I went back to Toronto for a while at the end of 2025 to do another run of musical improv shows, because life is short and why the hell not. Here’s what I wore to a class and then a show. It was so cold in our theatre space that night that a sweet boy lent me his large black hoodie to wear over my jacket for a lot of the night, which only improved the look, tbh!
What I’m wearing:
• Red and black striped T-shirt – Forever 21, several years ago
• Black blazer – thrifted for a job interview circa 2012
• Black jeans – the Gap
• Black leather Doc Martens
• Vintage red leather Coach Willis bag
October 24th, 2025
Wore this to see some friends perform a sketch show at Second City downtown, after which I immediately subwayed across the city to Comedy Bar Danforth for a party they were throwing that night. I will take any opportunity to sip beer with cool funny people and laugh my ass off for hours!
I almost never dress femmey for improv shows that I’m performing in, because it can be impractical, but decided to bust out a fancy femme look for the comedy-nerd party. I joked on Bluesky that my improv friends might not recognize me in such girly garb, and funnily enough, one of them indeed did not recognize me in the low-lit theatre space, mistaking me for a stranger until, a few minutes into our conversation, she realized who I was. I found this hilarious – gender presentation is such a trip, man.
What I’m wearing:
• Little black dress – bought for a Bettie Page Halloween costume a few years back (this was one of the only dresses I brought with me to Toronto this time, because, like any LBD worth its salt, it’s damn versatile)
• Blue and black heart-print cardigan – H&M circa 2007
• Blue socks branded with the logo of the sex toy company Dame
• Black leather Doc Martens
October 25th, 2025
Wore this to go visit my friends Dan and Sarah for some Jackbox games, wine time, and gossip, which was our near-weekly tradition back when Sarah and I lived together throughout the first couple of pandemic years. Always nice to wax nostalgic with old pals! I’m reminding myself of Starrina with this look: “One does want a hint of color…”
What I’m wearing:
• Pink T-shirt – the Gap
• Black cashmere hoodie – a lovely (and cozy) gift from my wife’s parents
• Black leather jacket – Danier Leather
• Pink knit toque – gift from my mom
• Black jeans – the Gap
• Trusty ol’ Nikes
• Red leather Coach Willis bag
October 29th, 2025
After having to crank out 3 short blog posts + 1 song video all in one day (due to poor time management on my part), I was soooo ready to unwind with my evening plans: attending a screening of Cruising with some family members. The movie largely takes place in queer kinky nightclubs, so it felt à propos to wear a lotta leather! Also, incidentally, my late uncle Kevan’s legendary rock band Rough Trade wrote some songs for the Cruising soundtrack, and it was cathartic to appreciate his artistry in a roomful of enthusiastic queers. (He also co-wrote a song that’s in Love Lies Bleeding!)
What I’m wearing:
• Men’s black T-shirt – got accidentally mixed into my laundry once; deeply sorry to whoever I inadvertently stole this from, but it’s a nice shirt
• Black leather jacket – Danier Leather
• Black jeans – the Gap
• Black leather Doc Martens
• Tiffany’s dog collar
• Vintage red leather Coach Willis bag
• Prescription sunglasses – Zenni
Great photos by mb
December 14th, 2025
Worn to do a musical improv show! Wish I could remember what I was singing about in the middle one; I look rather impassioned… but I know the one on the right was during a scene where I had a crush on Santa Claus, hence the coquettish body language! My wife was able to attend this one and took a bunch of excellent film photos of our set. It’s always fun to introduce her to my ‘prov friends.
What I’m wearing:
• Teal long-sleeved shirt – gift from my mom
• Little black dress
• Black leggings – H&M
• Black leather Doc Martens
• Red heart-shaped glasses – Zenni
Photos by my mom
December 21st, 2025
My outfit for my last improv show of the year! I performed in the show and in the subsequent improv jam, then hung out with friends until the bar closed, and then some of us walked back to my parents’ place and chatted about life/love/art until 4 in the morning. Once again gotta give a shout-out to low-dose naltrexone (LDN), the medication I take for my fibromyalgia; I could have never done all that stuff in one evening pre-LDN!
What I’m wearing:
• Red A-line dress – H&M
• Black cashmere cardigan – the Gap
• Black leggings – H&M
• Black leather Doc Martens
• Pearl necklace – Horae
• Apple Watch
P.S. Want more posts like this? Check out the ‘outfit‘ tag!
