outfit

June 17, 2023

After recording my song video for the week, I changed into this for the rest of the day. (Not really sure why I almost always pick an outfit/”costume” for my weekly song videos; it’s just become part of the process for me at this point. That week’s song was a sardonic post-breakup anthem so I wore all black with a big red heart necklace.)

I wore this outfit to go to the park and write fanfiction while sitting on a bench. This has been one of my favorite pastimes these past few months – not just writing fanfic but specifically doing it while sitting outside, surrounded by people and birds and grass. The bustle of it seems to help with my creative flow, kind of like sitting in a café, only more summery. (Incase you’re wondering, the chapter I wrote on this day was a CBT-infused BJ scene.)

What I’m wearing:

• Dark green cropped T-shirt – Calvin Klein (it’s surprised me how often I’ve worn this since buying it – it’s just sooo comfy because it’s made of a modal blend)
• Dark blue plaid schoolgirl skirt – H&M; bought a size up from my usual size because I wanted it to sit at my hips and not my waist, so it wouldn’t be obscenely short on me (and honestly it’s still pretty obscenely short)
• Black leather Converse Chuck Taylor All-Star sneakers
• Tiffany & Co. dog collar
• Blue leather briefcase – Coach Outlet (it’s exactly the right size for me to slip my laptop, wallet, keys, phone, and headphones into it for jaunts to the park to write)

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July 15, 2023

I wore this to go see a one-person show, starring and written by one of the kids who was on the high school improv team I coached in 2011-2012. I say “kid” but that was actually so long ago that they’re all adults now, doing amazing stuff out in the world.

I pretty much always have a great time when I go see theatre by myself. This particular theatre was enforcing a mask requirement so I didn’t feel too nervous about it COVID-wise. I laughed and cried and marvelled and it was a lovely night.

What I’m wearing:

• Hippo Campus T-shirt – a gift from my brother
• Navy A-line skirt – Old Navy like a decade ago
• Black leather Converse Chuck Taylor All-Star sneakers
• Coach Rambler crossbody bag
• Custom-engraved “Daddy’s” heart-shaped lock from L’Amour-Propre worn on a chain

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July 21, 2023

All the Barbie fever had me feeling hype about the color pink, so here’s what I wore a couple days before going to see the movie.

My partner and I have developed a protocol for my current ~secret project~ where, when I hit certain milestones, they pay for me to have a nice solo dinner out somewhere. So on this night I got dressed up and went for a luxuriant meal at my local fancy steakhouse. I was reading a long Sherlock fanfic on my Kindle, and sipped cocktails while eating scallops, steak, and mashed potatoes. Perfect self-date, if you ask me!

What I’m wearing:

• Black dress – Grace Karin (bought when I dressed up as Bettie Page for Halloween a couple years back)
• Pink metallic cowboy boots – Jeffrey Campbell, a findom gift from my love
• Pink and blue silk headscarf – a gift from my friend Sarah
• Tiffany & Co. dog collar
• Coach Rambler crossbody bag
• Prescription sunglasses – Zenni

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July 23, 2023

My outfit to go see Barbie with some pals!

Dressing to a theme is so much fun. Some people on my Twitter timeline observed that we should all dress up for movies more often (those of us who like doing that, anyway) and I agree. Sometimes choosing a theme or goal aesthetic is the best way for me to motivate myself to get dressed and get out of the house, because I relish the femme challenge of it.

The movie was great! I only wished there was more Michael Cera, but, y’know. We can’t always get what we want.

What I’m wearing:

• Pink sequinned dress – Grace Karin
• Pink metallic cowboy boots – Jeffrey Campbell
• Coach Rambler crossbody bag
• Pink sparkly heart necklace – Tarina Tarantino
• Pink KN95 mask – MaskC (I’m not wearing it in these photos but you can see it in my hand, and it was an important part of the overall look)

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July 31, 2023

Another outfit for a cute solo date, this one a little more low-key – I went to my local British pub and had a delicious and indulgent meal while, again, reading Sherlock fic on my Kindle. I am a creature of habit.

The tote bag was a gift from the folks at Vibratex, the current makers and distributors of the legendary Magic Wand, and I love it. I’ve been putting various enamel pins on it, most of them Magic Wand-themed, to liven it up a little. I like that the message written on it is subtle enough that people don’t stare at me weirdly in public, but is a bit of a wink-wink-nudge-nudge to anyone who happens to know about the Magic Wand.

What I’m wearing:

• Navy T-shirt – Wythe Hotel (worn about a zillion times since I acquired it shortly after having my very meaningful 3rd date with my partner at said hotel)
• Black ruffly skirt – thrifted in 2007-ish; it’s been a loyal fave for many years
• Black leather Frye harness boots
• “I make magic happen” tote bag – gift from Vibratex
• My sub’s chastity key on a chain

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August 1, 2023

A little androgynous flavor for ya!

I wore this to go have drinks with an old friend/FWB who I met when we both worked at the same sex shop. We had a lively discussion over dinner and drinks, and then drunkenly made out in front of a subway station for a while. Ideal.

Then I wandered over to my parents’ house and hung out with my mama for a bit, catching up on what’s going on with her.

What I’m wearing:

• White V-neck men’s T-shirt – Hanes
• Black high-waisted straight-leg jeans – Madewell
• Black leather Converse Chuck Taylor All-Star sneakers
• Hair styled in a way I’ve been doing it a lot lately, which involves applying pomade when it’s wet, combing it all back so it dries perfectly straight/flat, and then flat-ironing it to give it some extra polish

November 2, 2021

Been so long since I wrote one of these posts that these looks are from ages ago! Yeesh! Oh well – enjoy this assortment of outfits, mostly from seasons that have now passed us by.

During the pandemic, when I haven’t been wearing sweatpants and nightgowns, I’ve been vacillating wildly between dressing colorful and hyper-femme, and dressing in a way that is more subdued and androgynous-leaning. I liked that this look incorporated elements of both; it made me feel very cute and like my gender expression was in line with how I felt on the inside.

Pearls truly go with everything, if you ask me. This hat doesn’t, but I wish it did.

 

What I’m wearing:

• “101 Kinky Things” snapback hat – custom-made by Printful
• Dark grey T-shirt – borrowed from Matt, I think?
• Black skirt – ASOS years ago
• Black leggings – Gap
• Black leather Frye harness boots
• Pearl necklace – a gift from Matt

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December 24, 2021

Quite possibly the ideal Christmas Eve ensemble. I love to dress for an occasion!

I wore this to go over to my parents’ house for our typical Christmas Eve festivities, which include watching It’s a Wonderful Life while eating my mom’s legendarily good macaroni and cheese. I wanted to wear something that’d be comfy enough for lounging around with my fam but was still a little fancy and Christmas-y.

The Four Seasons Total Landscaping shirt makes me smile every time I wear it because that whole debacle with Giuliani was definitely the thing that made me laugh the hardest during that whole election week. It was one comical bright spot in what felt like all hell breaking loose.

 

What I’m wearing:

• Dark green Four Seasons Total Landscaping T-shirt – bought from the landscapers themselves; I cut off the hem and neckline
• Red pencil skirt – American Apparel
• Black cashmere cardigan – Gap
• Black leggings – Gap
• Black sequinned Ugg boots (these are soooo warm and comfy)
• Green knit beanie – H&M
• Sparkly red heart necklace – Tarina Tarantino

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March 5, 2022

Sometimes Matt and I like to wear themed outfits for our phone dates, because we’re both nerdy in that particular way. On this night, we were planning on watching Spencer, the movie in which Kristen Stewart plays Princess Diana, so I did some research on famous Diana looks to help me put my outfit together.

I drew inspiration from the iconic ’90s silhouettes she was best known for wearing, and some of the bolder colors she wore. I also attempted a Diana-inspired makeup look, which was all about brown eyeshadows and pinky-nude lipstick.

I had also just recently gotten these Nikes in the mail after waiting over a month for them, so I was excited to show them off!

 

What I’m wearing:

• Blue dress – Joe Fresh (I originally bought this to wear on an anniversary date but it turned out to be much more conservative-looking than I thought it was gonna be; I usually like to show a little more skin on romantic occasions)
• Pink ribbon tied around my waist as a belt (I think this came with some PR mailer I’d received)
• Red socks – Gap
• Nike Air Force 1 low-top sneakers, in custom colors

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March 25, 2022

I wore this out to a solo dinner date, one of my most treasured traditions. I eat dinner by myself, sip a martini and read a book on my Kindle. It’s truly the best.

I used to feel weird about doing this, but then I started to view it seriously as an important element of how I express self-love (in addition to, y’know, masturbation, the bread and butter of this blog). It’s a time when I can be totally alone – though surrounded by strangers – and just focus on relaxing and recharging. I especially like to do it at the end of a long work week, or when I’ve just hit an important deadline and want to celebrate. But also, it can be nice to do it for no real reason at all.

Later that night I had a terrible shrooms trip, but at least before that, I was well-fed…

 

What I’m wearing:

• Pastel tie-dye KN95 mask – a gift from my roommate Sarah
• Royal blue fit-and-flare dress – H&M
• Light blue cashmere cardigan – Autumn Cashmere, vintage via TheRealReal (I wore it to my wedding)
• Black leggings – H&M
• Black leather Frye harness boots
• Sparkly blue heart necklace – Tarina Tarantino
• Raspberry leather crossbody bag – Coach

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April 20, 2022

This cardigan is just perfect. I bought it at the height of my obsession with “lovecore” fashion, and have worn it countless times since then. It’s cozy as hell.

One of the most memorable times I wore it was during my first solo shrooms trip. I knew I might be freaked out during the trip, so I wrapped myself up in love – or at least, that’s how I knew my shroomy brain would interpret this cardigan. I think it did keep me safe on some level, because that was one of the most euphoric trips I’ve had.

This wasn’t that day, though. This was an outfit I wore on a date with a guy I’m occasionally seeing. We sat and had drinks together in his fancy loft apartment and then did some sexy stuff and then he sent me home in an Uber. Living my best life.

 

What I’m wearing:

• Pink and red heart-print cardigan – Unique Vintage
• Black modal slip dress – Calvin Klein Sleepwear
• Black leggings – H&M
• Custom-color Nikes
• Raspberry leather crossbody bag – Coach
• Black KN95 mask

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May 5, 2022

I wore this on a date with that same guy. I bundled up because it was chilly and we’d previously had a date where we sat talking on a bar patio until my teeth were chattering from the cold. (That’s how you know the conversation is good – that you can be freezing and not care!) So this time I wanted to be prepared.

Black and red is a powerful color combo. I felt very confident in this ensemble.

 

What I’m wearing:

• Cranberry-red KN95 mask – MaskC
• Red knit cowl – an Etsy shop called Keely Devine that has since closed
• Black leather jacket – Danier Leather
• Black cashmere cardigan – Gap
• Black “Honest Dead’s” tank top – Pineapple Pinup
• Red pencil skirt – American Apparel
• Black leggings – H&M
• Black leather Frye harness boots

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May 12, 2022

This is the kind of outfit that I really admire on other people but struggle to wear myself. I think I read too many fashion magazines as a teen and really absorbed the message that folks with pear-shaped bodies, like me, should always emphasize their waist with clothes. But fuck that. This is what I felt like wearing, because my body was hurting and comfort was my priority, and it looked cute!

Incidentally, the sweatshirt is from my alma mater, which had recently changed its name from Ryerson University to Toronto Metropolitan University because of its namesake’s ties to the genocidal residential schools system in Canada. (You can check out the Indian Residential School Survivors Society website to learn more about that, and to make a donation to help folks who’ve survived that horror.)

 

What I’m wearing:

• Ryerson School of Journalism sweatshirt
• Long red modal nightgown – Calvin Klein Sleepwear
• Black leggings – H&M
• Custom-color Nikes

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June 26, 2022

This isn’t an ad, but: The lube brand #LubeLife recently launched a limited-edition birthday cake-flavored lube, and as part of their promotion for it, they sent out PR mailers to journalists which included the lube, an entire Milkbar birthday cake (I was so surprised!!) and this shirt, which I instantly loved.

The day before, Matt and I had gone out shopping together. I’d thought I was gonna buy a new pair of jeans and hopefully a black modal jumpsuit, but neither plan panned out. However, I did see this black pleated skirt at Uniqlo and immediately knew I needed it. I don’t care that I’m 30 now; I can still dress like a schoolgirl if I want to!!

 

What I’m wearing:

• White #LubeLife-branded muscle shirt
• Black pleated skirt – Uniqlo
• Black leather Frye harness boots
• Apple Watch with red leather band from an Etsy shop called Jewlz4less
• Pale blue Coach Mercer satchel

August 7th, 2021

I wore this to the post office to ship a few copies of my book to various heroes of mine who’d agreed to blurb it (some of whom’s blurbs are on the book’s website now!). The whole reason I got dressed up ‘n’ dolled up was that I wanted to shoot some photos with the books before I sent them off. Being surrounded by copies of a book you wrote is a rush unlike any other!

As a side note, if those of you who buy my book would like to post some saucy selfies with it on Instagram using the hashtag #101KinkyThings, that would delight me beyond measure.

 

What I’m wearing:

• Pink ribbed crop top – Forever 21
• Pink bralette – the Gap
• Black bandage skirt – Suzy Shier
• Black leather flats – J. Crew
• Tote bag – Her Highness
• Blue leather collar – L’Amour-Propre
• Black KN95 mask
• Tom Ford lipstick in “Cherry Lush”

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August 11th, 2021

Rocking those rockabilly vibes. I wore this to record an episode of Question Box and then to go out for a solo meal at my local pub. Bandanas are ideal for days when I simply cannot be bothered to style my hair.

At the pub, I sat reading a book on my Kindle, as I almost always do when I go on a solo date anywhere. On this particular day I was re-reading Under the Dome, my favorite Stephen King novel and maybe my favorite novel, period. It’s so apocalyptic and chaotic a story that revisiting it took my mind off the chaos of our actual real-life world.

This was also the anniversary of one of my worst breakups, a day that makes me feel oddly sad every year even though it happened ages ago. Always good to combat feelings of dread, anxiety, and depression with a cute outfit!

 

What I’m wearing:

• Black and white gingham romper – MeUndies
• Red bandana – possibly the Black Market years ago
• Black leather flats – J. Crew
• Pink leather Coach Cashin Carry tote
• Rouge d’Armani matte lipstick in “Lucky Red”

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August 16th, 2021

Been feeling like a tomboy sometimes lately, or at least feeling more in touch with the gender-agnostic aspects of my queer femme style. Snapback hats make me feel like I’m embodying the androgyny of all the hot queers I had crushes on in high school!

I put on this semi-athletic outfit to record a podcast episode and then to walk down to the harbor and back (about a 30-minute walk each way), something I often do when I need to clear my head or just stretch my legs. When I got there, I sat on a bench by the water and read a book for a while, occasionally taking a break to people-watch or to text with friends. What a blissful afternoon!

 

What I’m wearing:

• Teal and purple “Think Positive” snapback hat – MaruHats on Etsy
• Red button-up tank top – the Gap
• Black leggings – American Eagle
• Turquoise/pink/purple Nike sneakers – a gift from my love
• Pink leather Coach Cashin Carry tote
• Apple Watch with rainbow band – inherited from my spouse
• Floral-print mask – an Etsy seller

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September 16th, 2021

Speaking of snapback hats… I ordered this absolutely perfect custom-stitched one, featuring the title of my book, from Printful.com. Originally I went on there hoping to order a mug with the title on it instead, or perhaps a face mask, but then I saw that they offered this type of hat and was instantly sold. It was probably the most expensive hat I’ve ever bought ($43.50 including tax and shipping), but it was so worth it – I feel cute as heck in it and wearing it makes me into a walking billboard for my own book!

I wore this to (once again) go for a solo meal at my local pub. (They are always so happy to see me there. I love being a regular!) I was reading Gala Darling’s book Hologram Heart, which is a thoughtful and dreamy analysis of the various ways in which our past patterns and traumas shape our behavior in relationships, and how we can break out of those old cycles in order to form healthier and more harmonious connections with people we actually like. Gala is, as ever, brilliant and inspiring!

 

What I’m wearing:

• “101 Kinky Things” snapback hat – Printful.com
• Blue T-shirt – American Apparel
• Black skirt – ASOS
• Black leather Frye harness boots
• Blue leather Keith Haring Coach Rogue bag – gift from my love
• Black KN95 mask
• Revlon balmstain in “Sweetheart”

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September 17th, 2021

My mom invited me over to sip cocktails and hang out, and specifically told me to wear my new hat because she wanted to see it in-person, so I did. This was an ideal outfit for lounging around in her garden, martini in hand, while we caught up on each other’s lives.

Later that night, we watched a movie she wanted to show me, called Stalked by My Doctor: Patient’s Revenge. It was really goofy and broad, the way that Lifetime movies so often are, but it was entertaining in its own way, and (spoiler alert) had a surprisingly feminist subplot involving women conspiring together in order to bring down a problematic man.

 

What I’m wearing:

• “101 Kinky Things” snapback hat – Printful.com
• Purple floral-print dress – H&M
• Turquoise bralette – Aerie
• Black leather Frye harness boots
• Revlon balmstain in “Smitten”

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September 18th, 2021

One more outfit with this hat… for now, anyway…!

I wore this to go out to karaoke with my friends Dan and Sarah. Karaoke was one of the last activities the three of us did together before the world shut down in March 2020, so it was surprisingly emotional to return to it now that we’re all vaxxed. We were really excited to see our favorite karaoke hostess Elyse again – she brought the house down by beginning the evening with a mesmerizing rendition of “Wild Horses.”

I sang “Bouncing Off the Ceiling” by the A-Teens, a dependable bop. The bar had put safety measures in place such as sanitizing everything between singers and requiring that we each used our own “mic condoms” (i.e. microphone covers) when we went up to sing. We were specifically told, “No dancing in the aisles! Only dance in your seats!” but, well, people were pretty excited to be at karaoke again, so that rule wasn’t followed too stringently…

 

What I’m wearing:

• “101 Kinky Things” snapback hat – Printful.com
• Green tank top with rainbow triangle – bought from Tegan and Sara’s merch table at Pride several years ago; if I’m not mistaken, this design is by Emy Storey, Sara Quin’s ex-wife and long-time collaborator
• Black skirt – ASOS (I really wish I had bought more of these, I wear this one so much)
• Black leather Frye harness boots
• Coach Rambler bag in “hibiscus”
• Black leather jacket – Danier Leather

June 30, 2021

My beloved and I had plans for a long-distance date, i.e. I go to a bar/restaurant in Toronto and they go to one in New York, and we talk on the phone throughout. I was in a good mood that day, and felt like getting a li’l dressed up, with false lashes and all.

I went to my local British-style pub to sit on their patio. They’ve had a pineapple mezcal margarita on their menu lately and it is a divine drink to sip in summer while on an outdoor phone call with one’s far-away love. ❤️

A pro tip if you are intrigued by the idea of this type of long-distance date: I have found it helpful to wait until after I’ve ordered my food/drink to start the phone call, mostly so that I can explain to the server what I’m doing and let them know it’s 100% okay to interrupt me while I’m on the phone because it’s not, like, a business call or anything. Oftentimes they even think it’s cute once I fill them in!

What I’m wearing:
• Yellow dress – H&M
• Yellow/pink striped silk scarf – probably thrifted at Value Village
• Toy Story-print mask – an Etsy shop
• Pink leather crossbody tote bag – Coach
• Black leather ballet flats – J. Crew (surprisingly, they are holding up much better than my previous pair, the Carson style by Frye, of which I have destroyed TWO pairs just by going on lots of walks every summer)
• Blue leather heart-ring collar – L’Amour-Propre
• Apple Watch with rainbow striped band – a hand-me-down from my spouse
• Sugarpill “Saint” false lashes (the same style I wore on my wedding day!)

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July 10, 2021

I was recently asked to be an interviewee on a TV documentary that will be airing on the CBC called The Great Canadian Sex Survey. This was the day I went to their rented studio space, the Darling Mansion, to be interviewed on camera. They wanted to talk to me specifically about asexuality and the ace spectrum, but we also touched on a number of other topics during our ~2-hour interview, from masturbation to sexual shame to finding eroticism outside of sex.

I showed up with frizzy hair and a naked face, because I knew they had a hair and makeup artist on set. She introduced herself when I arrived – her name is Vanessa Baudner and she’s a delight – and we chatted away while she styled my hair and gave me, at my request, winged eyeliner and a bold lip. (The lip is not pictured because she hadn’t put it on yet when I took this selfie.) It had been years since anyone but me had done my makeup – what a relaxing treat!

I thought this red dress captured the “professional, but fun” vibe I hoped to convey in the documentary, but they had also asked me to bring some alternate wardrobe options in solid colors. As it turned out, we were filming in a room with red and gold wallpaper, so they thought a different color would pop better; I switched this one out for a blue dress I’d brought, which looked great with my red lip. I’d been worried about seeming socially awkward upon being thrust onto a film set with a crew of about 7-8 people, but it was actually a super fun day!

What I’m wearing:
• Red dress – bought from Winners many years ago to wear to a wedding rehearsal dinner; the brand is Monteau
• Black leggings – H&M (the sound tech guy was confused by these at first but the waistband ended up being a great place to attach the machinery needed to run my clip-on microphone)
• Black leather Frye harness boots
• Blue leather heart-ring collar – L’Amour-Propre
• Canvas tote bag packed with extra outfits and makeup – Her Highness
• Black KN95 mask

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July 13, 2021

This was my new cane‘s maiden voyage. Having never used a cane before (except for possibly as a prop in some high school drama scenes?!), I wanted to practice the coordinated motions involved in walking with one. Before researching it, I didn’t know, for example, that you’re generally supposed to use the cane on the side opposite your weak/sore/injured side. Thanks, random mobility-aid educators on YouTube!

I walked around my neighborhood for about 20 minutes, practicing syncing up each step with the cane and moving some of my weight over onto it to alleviate the pain in my left knee. I wore headphones because I was (perhaps slightly irrationally) worried people would loudly comment on my cane, ask me questions about it, etc., but I don’t think anyone did. By the end of my walk, using the cane felt much more natural than it had when I started. Yay!

What I’m wearing:
• Navy “making it happen” T-shirt – Forever 21
• Black bandage skirt – Suzy Shier many years ago
• Black leather Frye harness boots
• Pink leather crossbody tote bag – Coach
• Blue leather heart-ring collar – L’Amour-Propre
• Black KN95 mask
• Chrome-plated blue wooden cane – Fashionable Canes
• Bright blue Cowin E7 headphones – a gift from a fan of mine who is a headphones fetishist

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July 22, 2021

Unfortunately I didn’t think to take a full-body photo of this outfit, but this is what I wore to attend a movie theatre screening of Bo Burnham’s Inside with my friend Dan. It was my first time being in a cinema since before the pandemic – pretty weird!

After weighing numerous outfit options relevant to the film – including wishing I owned white overalls and trying to decide whether cosplaying as the “Welcome to the Internet” guy would be feasible – I ultimately settled on an ensemble inspired by one Bo wears in his song “White Woman’s Instagram.” True, it’s not quite as striking as seeing a 6’5″ male comedian wearing nothing but a plaid flannel shirt shrugged off one shoulder, but it’s something!

The audience at the screening was much more subdued than I had expected. No singalongs or hands waving in the air. It was still a fun time though!

What I’m wearing:
• Green/blue plaid flannel shirt – the Gap last fall; I think this was the first time I’d ever actually worn it?!
• Black modal slip dress – Calvin Klein Sleepwear (I love that this nightgown is outdoors-appropriate and layers seamlessly under anything)
• Blue lacy bralette – Aerie
• Black leather Frye harness boots
• Blue leather heart-ring collar – L’Amour-Propre