July 3, 2022
My spouse asked me on a long-distance date, wherein we each go to a restaurant in our respective cities and talk on the phone while we eat. I wore this outfit to Blu Ristorante to sip some fancy cocktails and eat some delicious butternut squash ravioli while my love and I caught up about our days.
I had just recently acquired these black leather Chucks after going back and forth on them for a long time. Despite loving the aesthetic of this particular shoe (and owning a similar, dark purple pair back in high school), I was worried they would give me Bad Gender Feelings, as sometimes happens when I wear something that veers a little too far past the borders of my particular femmeness. But I’ve actually worn them so much. They go with pretty much every casual outfit, and – as this one shows – are even suitable for some dressier looks too.
What I’m wearing:
• Navy figure skater dress – American Apparel
• Black leather Chuck Taylor All-Star high-top sneakers
• Black leather Coach Station bag – vintage on eBay
• Apple Watch with red leather band from Jewlz4less
• Teal leather Tiffany & Co. dog collar – a gift from my love
July 4, 2022
It’s funny how I thought these shoes would feel too far afield from my femmeness, but then they ended up sort of stretching my femmeness to accommodate them, in a way that I’ve really enjoyed.
While I’m wearing this shirt almost as a tunic or dress in this ensemble, it was sold as a regular unisex tank top by American Apparel when I bought it several years ago; I got two of them (this one and a light teal one) and went up a couple sizes so I could wear them as nightgowns around the house. I’ve rarely worn them out but liked how the colorway looked with these shoes.
I love wearing pearls with more androgynous-leaning outfits like this. They lend a tinge of feminine sweetness to the look, balancing it out.
What I’m wearing:
• Slate grey “Lesbian Gay Bisexual Transgender Pride” tank top – American Apparel
• Black leggings – Gap
• Black leather Chuck Taylor All-Star high-top sneakers
• Black leather Coach Station bag – vintage on eBay
• Pearl necklace – gift from my love
• Apple Watch
July 12, 2022
Calvin Klein makes some of my very favorite loungewear; I have practically worn my CK modal nightgowns to shreds at this point. In trying to ascertain whether they made any comfy clothes that were actually meant to be worn outdoors (not that there’s anything wrong with just rocking sleepwear in public), I saw that they had this great modal tank dress. It’s a longer, looser cut than I’d normally feel comfortable wearing, but the fact that it’s black lends it a sort of simple sophistication that I nonetheless enjoy. Incidentally, this dress is now my favorite thing to wear for air travel – over some leggings and under a cashmere cardigan – because it’s so damn comfy.
I wore this outfit to go have drinks at my local pub with an old friend who I used to date. We caught each other up on our lives over a couple pints, and then I sauntered back home in the lingering summer-evening light.
What I’m wearing:
• Calvin Klein compact modal tank dress
• Black leather Chuck Taylors
• Pink leather tote – Coach
• Apple Watch
• Blue and black sunglasses – purchased at the hotel gift shop at Woodhull 2017; I wore them a lot to hide my tears while mourning a breakup that happened shortly thereafter, and this was the last time I wore them before they broke and had to be thrown out
July 23, 2022
Another look for getting drinks nearby with an old friend (a different friend this time). It’s hard to put together an outfit that is both amenable to the heat of summertime in Toronto and relatively presentable-looking, so I gave up and wore a bumblebee romper instead.
Kidding aside, I kinda live in MeUndies rompers during the warmer months, both at home and while out and about. They’re incredibly comfy, breathe relatively well, and come in an ever-changing assortment of eccentric prints – ideal.
What I’m wearing:
• Bumblebee-print modal romper – MeUndies (who also, no doubt, made the underwear I was wearing that day – my steadfast dedication to certain brands is a very stubborn-Taurus trait, huh)
• Black leather Chuck Taylors
• Pink leather tote – Coach
• Pink rhinestoned heart necklace – Tarina Tarantino
• Matching KN95 mask – MaskC
August 24, 2022
I wore this outfit in the evening after Matt and I had gotten back from an afternoon spent at the local nude beach, Hanlan’s Point. (If you’re curious, you can read about my experience there in this newsletter essay or hear about it in this Dildorks bonus episode.) When we got home, we showered off all the sand – SO MUCH SAND – and then rested and hydrated for a bit before getting dressed for dinner.
We went over to El Rey, a fantastic Mexican restaurant/mezcal bar in downtown Toronto, for margaritas, tacos, etc. Their patio was super chill and everything we ate and drank was excellent; would recommend.
What I’m wearing:
• Pink and white striped linen shirt, tied into a bow in the front – Old Navy
• White tank top underneath (unseen) – a gift from the brand #LubeLife
• Blue pencil skirt – bought from ASOS several years ago and subsequently tailored to fit me better
• Black prescription sunglasses – Zenni (I love these and kinda want to wear them all the time)
• Pink leather tote bag – Coach
• Black leather Frye harness boots
September 18, 2022
While visiting New York for a couple weeks, I wore this to go have brunch with my friend Brent on a patio in the Queens neighborhood he’d recently moved to. It turned out that the restaurant had a policy where every entree optionally came with a free drink (mimosa, bellini, etc.), which we had in addition to some fruity frozen cocktails we spotted on the menu… so, needless to say, our brunch got a bit boozier than anticipated, but for me and Brent, that mostly just means we talk about sex more and make more puns.
My spouse bought me these jeans several months ago and, while I love their flattering high-rise cut and they’re probably my favorite jeans I’ve ever owned, I haven’t been able to bring myself to buy another pair for my collection (maybe in a navy), because they cost $128 and I wear jeans so seldom that that seems steep. But I will probably wear these until they’re falling apart.
What I’m wearing:
• Red T-shirt featuring a fun illustration of the Hitachi Magic Wand – Pen & Kink
• Black high-rise vintage-wash jeans – Madewell
• Black leather Frye harness boots
• Red rhinestoned heart necklace – Tarina Tarantino
• Red heart-shaped leather bag – Kate Spade (isn’t it the best?!)
September 23, 2022
My lovely spouse had been asked to officiate their sister’s wedding, so we took the train to Philadelphia for the weekend and stayed in a hotel there while joining in the festivities.
Matt’s suit, custom-made for the wedding (which you’ll see below), was burgundy, and we’d decided (as we often do) to coordinate our outfits. I saw this vintage Betsey Johnson dress in my size on eBay and impulsively snapped it up, knowing I probably wanted to wear navy to the wedding instead but imagining that this red dress could be my backup. I ended up wearing it to the wedding rehearsal and then the rehearsal dinner, which is where we were headed when these photos were taken.
It was a lovely, crisp day, the rehearsal went beautifully, and the food and drinks at the rehearsal dinner were as delightful as the company. When my fibro fatigue caught up with me, I said my goodnights and slipped away to take a hot bath in our hotel room by myself – at which point I read the last few chapters of Carrie Soto is Back and wept so hard at the book’s beauty that I think I freaked out my spouse for a sec when they arrived and saw my teary face!
What I’m wearing:
• Red brocade dress – vintage Betsey Johnson, bought on eBay
• Cropped red cardigan – Urban CoCo
• Opaque navy tights
• Red leather heart-shaped bag – Kate Spade
• Black heels – some random company on Amazon; bought as part of my Bettie Page costume for Halloween a year or two ago
September 24, 2022
Here’s what I wore for the actual wedding, which was wonderful, emotional and sweet. After having a transcendent brunch, just the two of us, at The Love, we got all dolled up in our hotel room and then caught a shuttle to the venue, where photographs were taken for a while before the event itself started.
Matt let me help them choose some of the accoutrements they wore with this stunning suit; my main contributions were finding the pocket square they went with (it’s barely visible here but had a vivid red-and-blue abstract floral pattern) and picking a shade of lipstick that matched their suit almost exactly. It was “Velvet Jazz” by Lisa Eldridge, and we each bought a tube and both wore it to the wedding. Cute.
What I’m wearing:
• Navy sequinned dress – Le Chateau (I had wondered if it was a tad bit too sexy or flashy for a wedding but I think it ended up being fine)
• Cropped red cardigan – Urban CoCo
• Opaque navy tights
• Red leather heart-shaped bag – Kate Spade
• Black leather heels – Amazon
• Red rose hair accessory – Amazon
• Red rhinestoned heart necklace – Tarina Tarantino
• False lashes – Sugarpill