What to Wear on Valentine’s Day

Not to get too Hallmark on you, but I kind of love Valentine’s Day. Unlike when I was younger, my enjoyment of this weird invented holiday no longer depends entirely on my partnered-vs.-non-partnered status at the time (although that is a factor) – mostly I just view Feb. 14th as an opportunity to celebrate the very notion of love. And what better way to do that than by dressing like a walking embodiment of romance?

As you can see from the collage of my past Valentine’s outfits above, there are some common themes in my overall philosophy for Valentine’s Day dressing… While you are (obviously) not in the least obligated to follow any of these directives, here are my core commandments for assembling a Valentine’s outfit, whether your plan is an over-the-top candlelit dinner with your sweetheart, a raucous “Galentine’s” celebration with some friends, or a solo hangout at home watching rom-coms!

Pink and red are key. The way I see it, this is literally the only day of the year when pink and red don’t look overly cutesy together. (Or rather, they do, but that’s the point.) Comb your wardrobe for anything pink or red and figure out how you can pair various items. You can go as subtle or as bright as you like – though of course, I favor a loud and proud aesthetic!

Go wild with hearts. This, again, is the only day of the year when you can wear as many heart-themed items as you want and people will think it’s… slightly less weird than they might otherwise. 😂💖 Tarina Tarantino does the best heart-shaped jewelry (unless you have Tiffany’s money, but honestly, I’ll take a flashy giant rhinestoned heart over a small understated silver one any day), and typing “heart” into the search bar of any clothing or accessories website will bring up a lot of cute stuff. Also great: anything floral-print or polka-dotted.

Choose romantic fabrics. What does this mean? Well, that’s up to you. I think some fabrics are traditionally coded as delicately feminine and thus romantic, like tulle, chiffon, and lace. But sensual fabrics like velvet, silk, and satin carry their own romanticism as well. Anything swishy and/or soft to the touch is a good pick. (And hey, if you’re a kinkster comme moi, maybe leather and latex are the most romantic materials you can think of!)

Dress to match your partnerif you have one and you’re both into that! What would normally seem ridiculous can just seem sweet on Valentine’s. Dressing in sync can be a visual manifestation of your luuuv.

Hide something fun underneath. Even if you’re not much for high-end hosiery and luxury lingerie (and I don’t blame you – that stuff’s expensive and high-maintenance, though it is beautiful), you could still delight your partner (or yourself) with some Valentine-y undergarments of some kind. MeUndies makes adorable matching heart-print underwear sets every year that are definitely worth a look!

Wear what your partner thinks you look hot in. This one is fully, 100% optional, because 1) you might not even have a partner, 2) you might not trust or prefer their aesthetic tastes over your own, and 3) you might not even know what they like you in, especially if it’s a new-ish relationship. But say your sweetie has told you they love you in striped stockings, or a well-fitting suit, or peeptoe heels, or with your hair slicked back – there’s no better occasion to wow your love with your choice of ensemble.

Go all out with your makeup, if you wear makeup (or if you don’t regularly wear it but want to on Valentine’s!). I like a classic smoky eye and red lip – that’s what feels the most romantic to me – but if you’ve got shimmery pink eyeshadow, or big fluttery false lashes, or iridescent pink lipstick, or stick-on hearts and cosmetic glue, by all means, use ’em! Be sure to consider longwear formulations if you’ll be out late and/or you plan on doing some kissin’.

Keep the weather in mind, because – while I do want you to look and feel excellent – in many places, it is snowy and/or freezing in February! Maybe you don’t want to be skidding around in your sky-high suede heels, or shivering sullenly in your translucent tights. If you must be impractical (and I get it), at least throw on a warm scarf and great coat when you go out, and maybe switch from boots to pretty shoes when you get where you’re going. Fashion is fun, but it’s not worth getting frostbite or a broken ankle for!

Wear what you feel sexy and gorgeous in. You can ignore every other rule here if you want, but this one is vital! Whether you’re making heart-eyes at your sweetie across a restaurant table, giggling with friends over a tipsy game of Spin the Bottle, or lounging solo at a cocktail bar with your favorite romance novel, you’re gonna wanna feel like a babe – whatever that means to you personally. Think about the times when you’ve felt your hottest/prettiest/handsomest and try to incorporate some elements from those past looks into your present one.

What do you plan on wearing for Valentine’s Day?

Behind the Seams: Couples’ Edition

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.

Matt 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:


December 30, 2019

For Matt’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!

Matt 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 Matt)
  • My collar again

Photo by Scott Stanger

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 Matt 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“!

Matt 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 Matt, 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)?

5 Types of Lingerie to Incorporate Into Regular Outfits

Lingerie, like manicures and 9-step skincare routines, is one of those things I’ve always wished I was more into than I actually am. It seems like an important hallmark of a certain type of femme presentation, one I long to embody but just can’t be bothered to pursue most of the time. After all, lingerie is expensive, sometimes cumbersome, and not even guaranteed to be seen by many people – so when I have a little spare cash to spend on feminine treats, usually I’ll go for a new dress or lipstick in lieu of a new bustier or garter belt.

That said, I’ve read a couple of articles lately on incorporating sexy-wear into your everyday ensembles – this one by Rae and this one by Cora – and it got me thinking about the few types of lingerie I do like to wear, often outside the confines of my bedroom (scandalous!). Here are some of them…

Slips

I love slips, and their closely related cousins, babydolls and chemises. Not all of them are long enough – or opaque enough – to don as outerwear, but when I find one that is, I immediately start plotting outfits.

As you can see in these photos, you can wear a slip in various different ways to make it look like a dress, a skirt, or a shirt, depending on what you layer over top of it. It can appear casual with a T-shirt thrown over it, or you can emphasize the ornate formality of a lacy slip by pairing it with tights and heels. A cardigan is a good happy medium between the two: it “dresses down” your slip a little, so you don’t look like the weirdo who showed up to a frat party in fine silks (although: you do you!).

I particularly like to wear slips in the summer, when “real clothes” can feel oppressively excessive. They can look like a fully thought-out outfit when worn with ballet flats and maybe a coordinating hair accessory, but they’re actually super easy and quick to put on, and comfortable enough to wear all day.

One tip: since slips are intended to be underwear, they don’t always conceal stuff like nipples and panty lines very effectively. For this reason, you might want to layer an additional slip or half-slip underneath, or a bodysuit.

Bodysuits

Speak of the devil… There are tons of gorgeous bodysuits in the world that are only supposed to be worn behind closed doors. Fuck that! If a piece of clothing I own is beautiful, I want to wear it outside, dammit. It’s just a matter of figuring out how to make these items more appropriate for public wear.

My favorite way to do this is to tuck a pretty bodysuit into a high-waisted skirt or a pair of jeans. You’ll probably want to wear a bra or bralette underneath to prevent flashing people, and this admittedly isn’t an appropriate type of outfit for, say, a church service or your grandmother’s potluck luncheon, but it’s a super eye-catching style that makes me feel like a total babe.

Pro tip: when shopping online for lingerie you intend to wear outdoors, always check out the loungewear section first. In my experience, it tends to contain the most street-appropriate bodysuits, camisoles, slips and chemises you’ll find anywhere on the site.

Bikini tops

I think I originally picked this up from teen magazines in my youth and it’s never really left me… If you’re wearing a high-waisted garment on your bottom half, and don’t mind showing some skin, you can get away with wearing a bikini top as a sort of abbreviated crop top. It’s not the most mature or sophisticated look – it makes me feel like a blonde PacSun model circa 2003 – but it works for some casual summery occasions.

If subtlety is more your style, you can also wear a bikini top under a dress or shirt, like a bra (see the rightmost outfit pictured). They usually peek out a little bit, offering a visually appealing flash of color or sparkle, and giving you the air of someone who’s ready for beach adventures at a moment’s notice. Of course, if you do intend on dropping by a beach/lake/pool/whatever, it’s nice to be prepared in the chicest way possible.

Garter belts and stockings

These are usually too finicky for me to bother with, but it’s nice to have them in your toolkit for when you want to feel really sexy and fancy. While currently mostly relegated to the sphere of the bedroom, garter belts and stockings used to be daily-wear items for women in the mid-century and beyond. They add some timeless panache to your ensemble when they peek out the bottom of a skirt or dress.

If a garter belt is too much work for you (and I truly don’t blame you), look for “stay-up” or “hold-up” stockings, which usually have some kind of sticky material on the inside of the cuff to keep them from sliding down your thighs. Genius!

Corsets and bustiers

I wore these in high school when I would go to see Rocky Horror, and they were the ideal thing, styled with shiny skirts, high-heeled boots, and ever-present fishnet tights. But let’s face it: that’s not exactly office attire.

A beautiful corset or bustier under a blazer might be, though, especially if you’re also wearing an elegant skirt or pair of pants, plus ideally heels. A lot of high-end fashion houses have even pulled inspiration from the realms of lingerie and fetishwear in recent years (and, well, recent decades), so – depending on your field – it may not be that weird for your outfit to contain a pop of lace or silk or corsetry. You might even look like the most fashionable person there!

Do you like to incorporate lingerie items into your everyday outfits? How do you do it?

 

This post was sponsored by the fine folks at Honey Gifts, which has a robust lingerie section containing all sorts of lovely and luxurious items!

Behind the Seams: Fetishwear & Mean Girls

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.

The event dress code said “fetishwear or all-black,” which I and the femme friend I invited both found daunting yet doable. I got dolled up, then trekked uptown to meet my friend walking-distance from the venue so we could head over together.

It ended up being pretty low-key and fun. We’re both on the shy side, so we didn’t play with anyone or even really talk to anyone, but we had a lot of fun sitting on the sidelines and catching up on each other’s lives while intermittently watching some of the scenes that happened. We didn’t see any hypno, but then, it can be a tough kink to spot. Instead, several impact scenes unfolded in front of us, including one that also featured rope suspension, forced orgasm play, and a mega-hot domly dom in a suit. Woof.

At the end of the night, I took a bus home, got McDonald’s as per my Sir’s instructions, and told him all about the party over the phone. Pretty sweet night out, all in all.

What I’m wearing:
• Hair in little buns
• Black skater dress – H&M
Pink leather chest harness – Stockroom
• Pink and white striped kneesocks – American Apparel
• Black leather Frye harness boots
• Eyeshadow and lipstick – the Sugarpill Oh Honey! collection


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.

The theme was open, so the stories told that night were a wild grab bag: a first sapphic experience, a chance meeting on a Megabus, ableism on dating apps, awkward Pride celebrations with homophobic parents, being outed by nosy bosses, and more. I sipped a double whiskey on the rocks and laughed/gasped all the way through the night.

I told a story too: the tale of my first knifeplay scene with Dick, way back in December of last year. I figured it was an appropriately scary story for this October event. I can’t believe I’d never told that one at TMSG before!

What I’m wearing:
• Orangey-red heart-print dress – CowCow
• Black Danier leather jacket
• Blue suede collar – L’Amour-Propre
• Black leather Coach Station handbag – vintage on eBay many years ago
• Black leather Frye engineer boots
• Revlon Fire & Ice lipstick (a classic, a legend)


October 3rd, 2018. October 3rd is Mean Girls Day and it was also a Wednesday – so, obviously, I wore pink.

My regular Frye harness boots had cracks in the soles so egregious that my socks got soaked when I walked in them on rainy days, so I’d set them aside for the time being. That meant that my rainbow glitter Doc Martens got to see the light of day again.

I wore this outfit to a local café to do some dayjob work, and then back home to write this post.

What I’m wearing:
• Pink T-shirt – Gap (it needs to be ironed!)
• Black Danier leather jacket
• Blue sparkly heart necklace – Tarina Tarantino (current fave jewelry item)
• Black leggings – H&M
• Rainbow glitter Dr. Martens – Urban Outfitters a while ago

Behind the Seams: Besotted in Boston

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.

Thus attired, I trekked down to Toronto Island to catch my flight from Billy Bishop airport, read The Magicians on the plane, then dragged my luggage onto a Boston city bus and walked a few blocks to the Godfrey Hotel, where Sir met me in the lobby. He looked – as ever – heart-stoppingly handsome, and highly excited to see me.

We checked in and took the elevator up to our 6th-floor room, where, at first, we just cuddled and kissed and held each other. (Reunions in long-distance relationships are often like this.) But, before too long, we were having loud and messy sex involving a lot of toys, biting, punching, and slapping, because we’re us.

Later that night I changed into a slinky black and silver dress for a night out on the town: dinner at Bistro du Midi and an Alina Baraz concert. We danced and swayed and giggled and he bit my shoulder hard enough to leave a bruise. It was all very romantic.

What I’m wearing:
• Yellow unisex Hippo Campus T-shirt – bought at their merch table at a show in Brooklyn back in February
• Black leather Danier jacket with pins from Kinktionary, L’Amour-Propre, and MaxFun
• Black leggings – H&M probably
• Black leather Frye harness boots
• No makeup, because it was all packed!


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.

Sir chose this dress for me in the morning – it’s one of his faves – and then we went to Tatte for brunch, which was delicious and beautiful. From there, we took a Lyft to Harvard Square, stopped into Good Vibes to look at sex toys, and wandered onto the Harvard campus. We found a little nook in which to make out for a minute or two, because it seemed important that we kiss at Harvard, or just that we kiss in general. Then we sat on the steps in front of Widener Library and peoplewatched for a bit. (People dress great at Harvard.) We stopped by Amanda Palmer’s favorite haunt, Café Pamplona, for drinks before deciding on our next move.

Sir wanted to check out the Boston Public Library, which was beautiful. We walked around looking at statues and art, and then sat in the courtyard and did an impromptu hypno scene in that serene little space. I felt so safe and happy. We strolled back to our hotel through the Boston Common. Later that night, we got dressed up for steak at a jazz club, cocktails at Drink, and, uh, a watersports scene.

What I’m wearing:
• Blue and white floral-print dress – H&M
• Black leather Danier jacket with pins from Kinktionary, L’Amour-Propre, and MaxFun
• Hot pink Kate Spade New Bond Street Florence satchel
• Black leather Frye harness boots
• Navy suede collar – L’Amour-Propre


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 The Gallows for brunch; I had fried chicken and pancakes that were memorably yummy.

On our way back, we stopped in the park to peoplewatch, giggle, and kiss. Sir provided a running commentary on some folks who were doing strange airborne couples’ yoga a ways away from us, making me laugh so hard I couldn’t breathe.

We checked out Newbury Street, stopping into a café and a clothing store. Sir bought us chocolate truffles at a fine chocolatier, which we ate on a park bench, talking about how much we were going to miss each other.

Sir had a hankering for oysters (and, as they say, when in New England…) so we went to the Island Creek Oyster Bar. We worked our way through 12 oysters and a few drinks while doing our traditional end-of-date debrief: discussing our favorite parts of the weekend, what we hoped to try more of, and when we’d see each other next.

He took me back to the hotel to grab our bags, then kissed me goodbye and stepped into a car to the train station. I watched him drive away, feeling very in love and only a little bit sad.

What I’m wearing:
• Turquoise and pink floral-print dress – CowCow
• Black leather Danier jacket with pins from Kinktionary, L’Amour-Propre, and MaxFun
• Hot pink Kate Spade New Bond Street Florence satchel
• Black leather Frye harness boots
• Navy suede collar – L’Amour-Propre