I’ve always enjoyed the thought of dating someone whose personal style mattered to them, whose grooming and aesthetic were joyful components of their life rather than just perfunctory choices. I admired couples who posed together for chic outfit photos on my favorite lifestyle blogs, and occasionally tried to match my ensemble to my beaux’. This wasn’t just vanity for me – a couple’s outward coordination feels to me like a manifestation of their inward coordination (though of course this isn’t the case for everybody). Matching felt like a love language. Dressing up to delight a partner felt like an act of sweet service.
I’m fortunate that my partner now agrees with me on these points, and we love to go on fancy dates together dressed in outfits that subtly reference each other’s (and also sometimes get us free drinks). Here are some of my faves we’ve worn lately…
December 13, 2019
For our two-year anniversary, we packed up our stuff for a brief staycation at Toronto’s beautiful Broadview Hotel. I’d watched its construction with eager fascination years ago (it was built from a broken-down and legendary old strip club called Jilly’s) but had never stayed there, so I was excited to check it out.
After getting very pretty, we went to the hotel’s rooftop bar for a drink, and then to Michael’s on Simcoe for a magnificent steak dinner. I made our waiter cry by thanking him for correctly gendering my partner. It was a good night.
mb is wearing:
- Grey suit – Suitsupply
- White collared shirt
- Blue/pink/silver tie – vintage Emilio Pucci and was one of my birthday gifts for them the previous year (I love Pucci!!)
- Black leather shoes – Allen Edmonds
- Tom Ford lipstick in “Cherry Lush”
I am wearing:
- Shiny blue halter dress – Le Chateau
- Black tights
- Black leather pumps – Naturalizer
- Blue leather collar – L’Amour-Propre
- Tom Ford lipstick in “Cherry Lush” (we unknowingly bought each other the same lipstick for our anniversary like a couple of nerds)

December 30, 2019
For mb’s 29th birthday, we went out with a bunch of their pals for a huge prix-fixe meal at a fancy Japanese restaurant, followed by cocktails at Kind Regards. I felt so surrounded by love and joviality all night!
mb is wearing:
- Pink blazer – thrifted earlier that day at a Goodwill in Manhattan; we were shopping for fancy vintage clothes to wear to a different party (see below) and I saw this, gasped, and MADE them try it on – doesn’t it look amazing?!
- White collared shirt
- Blue/purple/pink tie – also vintage and also a gift from me last year; this one’s by Express Design Studio
- Black jeans, I think?
- Black and gold “Please use they/them pronouns” pin
I am wearing:
- Black sparkly velvet halter dress – Forever 21 a few years ago
- Black cashmere cardigan – the Gap
- Black leggings – H&M
- Black harness boots – Frye (an anniversary gift from mb)
- My collar again

January 4, 2020
In late 2018 I met the great Tara Isabella Burton after I read her first book and she interviewed me about kink for her second. This year, she invited mb and I to her “unwedding“: a black-tie party meant to celebrate her not getting married. The dress code said “as extra as possible” and we took that to heart.
The party was wild. I swilled prosecco and cocktails, exchanged cringey ex stories with a brocade-clad bartender, debated modern movies with a film critic, watched a YouTube-famous chef swing-dance to a live jazz band, met (and kissed) a beautiful litigator, met (and kissed) a flirtatious professor, wobbled around in my heels, and just generally had a raucous good time. Congrats to Tara on “not getting married today“!
mb is wearing:
- Blue velvet blazer – J. Crew (I SHRIEKED when I saw this; as has previously been discussed, I have feelings about velvet)
- White collared shirt
- Charcoal grey suit pants – also J. Crew
- Red and navy tie – also J. Crew
- Black leather shoes – Allen Edmonds
I am wearing:
- Red lace dress – vintage via my mom; she bought it in the early ’80s to cover a Phantom of the Opera premiere for Global TV, and it miraculously fits me perfectly
- Blue satin Christian Louboutin peeptoe pumps – a gift from mb, bought vintage from TheRealReal at 75% off the original price
- Blue tulle hair clip – a gift from my friend Eric years ago
- Silver sparkly clutch – bought vintage for $10 from the now-defunct Melanie’s Closet in Kensington Market in 2007
- My collar again
Do you ever dress to match your partner(s)?




September 29th, 2018. A new-ish dungeon space in my city was having a hypnokink play party, and my Sir encouraged me to go. This is normally the kind of thing that would activate my anxiety a lot – and, indeed, it did – but, as per usual, having been instructed to do it anyway by my beloved dom made me feel better equipped to overcome my fears.
October 2nd, 2018. I wore this to Tell Me Something Good, the monthly sexy storytelling event I love so much. My Sir chose my outfit, as he often does when I go to events.
October 3rd, 2018. October 3rd is
September 21st, 2018. I always get anxious about travel. It can be an anxiety-provoking thing for anyone, but it’s particularly become a trigger for me since I missed a flight a couple years ago due to a transit miscalculation. So when my Sir picked the outfit he wanted me to wear to the airport for my flight to meet him in Boston, he chose an ensemble he knew I’d feel comfy in: leggings, boots, and a shirt bearing the name of my favorite band, Hippo Campus. What a thoughtful sweetheart.
September 22nd, 2018. While we mostly just wanted to spend the weekend kissing and fucking and hanging out (#LongDistanceLyfe), we each had some touristy things we wanted to do in Boston, so we decided to do ’em on our wide-open Saturday.
September 23rd, 2018. We made use of our last remaining hours in our beautiful hotel room by having sleepy morning sex and testing out a new lipstick for blowjob purposes (more on that coming to a blog near you in a while!). We left our bags with the concierge and strolled over to
June 22nd, 2018. It’s become tradition that my Sir chooses my outfit for days when he arrives in Toronto to visit me for a weekend. I mean, he chooses my outfits at plenty of other times, too, but this tradition feels particularly salient because he usually sends me my instructions a few days in advance, and then I get to spend those days picturing how he will remove those specific clothes from my body once we’re finally, finally together again.
June 23rd, 2018. It wouldn’t be a Sir-and-little-one weekend if there wasn’t at least one fancy night out on the sched. Sir chose this outfit for me before we hopped in an Uber to
June 26th, 2018. On Sir’s last day in Toronto this weekend, we went for lunch with