A Very Pink Day

A few weeks back, my wife tells me she’ll be out of town on an upcoming Saturday night. I say, “No problem. . .maybe I’ll send the kids to grandma’s house and have a night out myself.” I contact Claudia and she’s all in. With the date set, we get to the business of figuring out an activity. We talk about an Afro-fusion club, which seems cool and definitely fun, but it’s not exactly what we’re looking for. We look around some more and I discover that Untitled Supper Club has a blues singer, Ivy Ford, that night. I send the link to Claudia, but before she even reads it, I make a reservation for 4 people. I’ve been to this swanky place before and with the pandemic we’ve been desperate to see some live blues again. Claudia is not sure, but I send her a YouTube video and she’s immediately sold. There’s some other logistical issues, but we’ll get back to those later. Now that a venue has been selected, let’s talk about outfits. 

My original thought was the salmon and black dress I bought back in November. With the spring weather, I figured it was time for that girl to make her debut. However, as I said, I’ve been to Untitled before and it’s a pretty swanky place with a Speakeasy theme. The springtime look of that dress would certainly fit the season, but I was feeling like I wanted to go with something a bit more sultry. Then, I remembered this Bebe dress I bought online on a lark. Originally, I wasn’t all that impressed and I almost sent it back. Last month, I got some pics with it at home in full makeup, but remember being somewhat underwhelmed. Just in case, I looked up the pics again and was like, “Wait a minute. This might work.” So, I called on the hive mind and posted a couple pics on Facebook. It was a resounding hit, so then I was thinking, “Okay, let’s try this” It’s a black number, with off the shoulder sleeves and a ruffle hem that’s shorter in the front than the back, exactly the kind of dress one would expect from Bebe. By the way, I got it for 70% off, which is why I was hesitant to send it back. The next concern was how to accessorize. My main question was nail color, which I put to the Facebook gang. Lots of red and french tip suggestions, but those always seem so cliche to me. I was toying with the idea of a light pink, kind of a ‘60s style. This idea was independently suggested by a few Facebook friends, all of which are usually spot on with their style advice. 

Potential dresses.

The Friday before the Saturday, I had to work in the morning and didn’t get home until 3:00 p.m. My daughter had online school until 3:30 and promptly got to getting ready to go. But, being 13, the first 45 minutes of that ‘getting ready’ activity was putting on makeup — my wife often jokes about this and keeps saying that she’s her daddy’s daughter. We finally get out the door at 4:30, the exact worst time for traffic, but not as bad as it could have been. After dropping them off, I tried something different. Usually, I get my nails done in the morning, but figure I could save some time by getting them done the night before. So, I find a salon about a mile from my parents house and go for it. The boy mode part is not an issue, I’m usually in boy mode at the nail salon. But, doing so way out in the suburbs is new for me. In the city, with a fairly large LGBT community, I’m guessing it’s not uncommon for a guy to be asking for pretty pink nails.

Her nails are pretty in pink.

I get home and have about an hour to start my packing before picking up my wife from work (as city folk, we only have one car). I’m guessing she noticed my pretty pink nails, but makes no mention of them. Back home I continue packing, but also try on the proposed outfits and a few others, of course with hip pads and various wig options (but no makeup) — basically a final check to see if things are feeling right. Also, a fair amount of that night was spent texting with Claudia about last minute logistics. 

Okay, let’s talk about those logistics. Due to the pandemic, Untitled, like most restaurants, are limiting visit time. They happen to be doing it based on party size: 1.5 hours for 2 people, 2 hours for 4 and 2.5 hours for 6. The reason I made the reservation for 4 people, was because the band started at 7:00 p.m., but the latest reservation I could get was 5:45, which would get us 45 minutes of band time. So, we proceeded to liberally invite friends to get the group up to 4 or maybe even to 6. There were a lot of maybe’s, but it was only Rubi and her friend who confirmed. But then, on Friday afternoon we had a late confirmation. So, I called Untitled and they were pretty clear that increasing to 5 would be impossible at that point. Claudia suggested changing restaurants. I didn’t like that idea and ended up changing the reservation to 5:15 which allowed for a party of 5. But, that meant that we probably wouldn’t be able to see the band. Not a great compromise, but we felt like it was our best option. After the change was official, I made the prediction that at least one person was gonna back out at the last minute. About 12:30 a.m., we get a text from our last minute addition, saying that she had made a scheduling error and now wasn’t gonna be able to make it. Of course, it was too late to change back to our original time slot. Claudia and I were basically stunned by how quickly things had gone awry. But then, I was just like, “It is what it is. We’ll be fine and it’s still gonna be great night. No need to dwell on what cannot be changed”

The next morning, I’m up early. Get a solid breakfast, hit the shower and shave my face and chest — legs and armpits were cleaned up a couple days earlier. I’m out the door by 9:30, which seems kinda early to be checking into a hotel. But, this particular hotel allows for an early checkin, so it’s no problem to arrive at 10:00 a.m. Rubi arrives at noon, dressed and ready for some shopping. I’m just finishing my makeup and glad she’s there to help me make some final outfit decisions. I’ve decided to go with the salmon/black dress for shopping, but need to decide on footwear. First option is black suede knee boots — a bold contrast that Rubi wholeheartedly approves. Second option is pink suede Mary Jane heels. Before I put them on, Rubi doesn’t look impressed. But once on, she says, “Oh? Those are kinda workin”. I’m less hesitant and immediately know that they’re exactly what I was looking for. We’re about to head out door when I get a text that Claudia is 10 minutes out. So, we stick around to welcome her and use the opportunity to snap some all important pics. 

Outfit choices for shopping.

It’s a beautiful day, so we decide to walk over to Block 37 in the Loop, which is just across the river from our hotel. Our first stop is Sephora, cuz I’m looking for a pink lip stain to match my nails. I quickly grab a sales associate and we head out on an odyssey, checking every brand and finally settle on a shade that’s not a perfect match but close enough. While there I get a refill on my Laura Mercier setting powder.

A few years back, a friend gifted me a sample size of this stuff and I was immediately hooked — it’s super fine and feels oh so luxurious while brushing it on. Also picked up a sample size of pore filler primer. That stuff actually works. I was lucky to get out the door for under $75 — that place is dangerous.  

Next stop was a place called Francesca’s. I’ve noticed it before, but have never been inside. It kinda looks like it has clothes for aging hippies — very Stevie Nicks-esk. Rubi was raving about it, so I figure what’s the harm. Turns out they have lots of cute stuff. I was particularly interested in the earring display and end up buying 4 pairs — wow, my wallet was really hurting by that point. Next was AKIRA, a favorite for both of us. Mostly glam clubbing clothes — perfect for dance nights in Boystown. I try on some crazy pink heels that totally match my nails. They actually fit, but are incredibly uncomfortable. Even if they weren’t killer painful, I probably wouldn’t have gotten them, cuz shinny patent pink stilettos are a bit to much, even for me. But, definitely fun to try on, especially since it’s a rarity for AKIRA to have shoes in my size. We make a quick sweep around the sales rack, but nothing catches our eye.

Last stop was the Macy’s across the street. First stop there is the MAC counter, cuz I need a refill on my makeup primer. You might be noticing that a lot of my makeup routine is about primers, finishing powders and setting sprays. Other than a regular skincare routine, those are actually the most important steps of the process. We poke around a bit and I find a pink eyeshadow, which might come in handy this evening. As I’m paying, the sales associates asks, “What’s the occasion? . . . Are you coming from somewhere?” Takes me a second and then I realize she’s asking why we’re dressed so nice. Thinking quick, I reply, “Oh, no occasion really. We’re out just because I needed an excuse to wear this fabulous dress.” She laughs and we chat a bit about people wearing formal wear to the supermarket, just cuz there’s no place else to go during a pandemic. As we’re leaving, one of the associates comes around the counter and gives us a big thank you for coming in and how she looks forward to seeing us again. Not sure what prompted that, but it was pretty cool — it’s nice to feel special. 

We make one last stop at the shoe department, which was utterly disappointing, but not all that surprising. It’s funny. This Macy’s, on State Street, doesn’t seem to have a great shoe selection, especially in comparison to the Macy’s on Michigan Avenue. Unfortunately, the one on Michigan Avenue is closing. It’s heartbreaking, because I’ve got so many great memories from that location and their selection on pretty much everything always seemed to be better. Yes, the struggle is real ladies, the struggle is real. 

Finally, we grab an Uber and head back to the hotel for some much anticipated “glamming up”. Back in the room, Claudia is still working on her makeup (turns out she snuck in a cat nap while we were out). I immediately get to working on my eyes, cuz I’m having an eyelash emergency. Just before getting in the Uber, Rubi informed me that both my eyelashes were falling off. Wonder how long I was walking around like that? I wasn’t so happy with the morning eye makeup anyway, so my solution was to just remove it all and start over. Of course, I used the new pink eyeshadow, which, as promised, was really high quality — guess I’ll be using more Mac in the future. I also went with even bigger lashes — yeah, I was in that kinda mood. Then, it was time for the new pink lip stain. Wow!! That’s really, really pink. Claudia and Rubi agreed, “That’s a lotta pink” I almost take it off, but Claudia convinces me to take the risk and go with your vision for the outfit. I get the Bebe dress on along with the black heels and furry purse, and it all comes together — everything black except for pink nails, lips and eyeshadow — I also pinked up my blush. Added pearl hoop earrings, skipped the necklace (to let my cleavage-less chest take center stage) and I was ready to take on the world. 

The Bebe dress.

The restaurant was just a block from the hotel, so we had a nice stroll with lots of other people enjoying the warm late afternoon weather (it was March in Chicago, so warm is defined as mid 40s). The hostess greets us with a giant smile and compliments us on our outfits. She’s wearing a silver sparkly dress, so we return the compliment. I ask if she got it at AKIRA (I always have AKIRA on the brain) and she says, “No, . . . it was an online store . . . vintage something or other.” I think for a moment and say, “Oh, I know. Unique Vintage.” She’s like, “YES! That’s it. How did you know?” Turns out I was seriously thinking about buying that exact same dress about a year earlier — it’s actually a flapper costume dress. The hostess mentions that there’ll be a band and a burlesque show later on and we should stick around. We look at each other, and say, “Sure, we’d love to.” Okay, maybe we will get to see some music after all. 

Julie and the hostess talk about shopping.

The dinner was fabulous, the drinks were scrumptious and the conversation was lively. When it came time for the band to start, the hostess stopped by and said that we were welcome to stick around — guess it pays to chat it up with the hostess. At the break, Claudia and I go upstairs and outside for a cigarette — the place is on the lower level and just as you enter, there’s a wide somewhat grandiose staircase leading to the speakeasy level. Coming in this second time we notice a giant mirror on the back wall just above the stairs. It’s a perfect picture spot . . . except, neither of us brought our phone. For a moment we don’t know what to do. Then, we notice that band had restarted. So, we look at each other and just start dancing. Dancing our hearts out at the top of those stairs in front of that giant mirror. It was one of those spontaneous special moments that makes you remember why life is worth living. 

We did a few other things that night, but I think I’ll just leave you here with the image of two girls dancing like nothing else mattered. “See Claudia, I told you it would all work out”

Cheers!

Tags: crossdressing, featured

Category: crossdressing, Out & About