Julie’s NYE Celebration — Kinda

Claudia, Rubi and I were planning a dinner outing for the Monday before New Year’s Eve. I had just gotten in a new sparkly skirt and suggested we glam things up and make the night into a Faux NYE. You see, Claudia and I are similar, in that we always spend the real NYE, quietly at home with the wife and kids. We would rather be out at a fancy party in fabulous dresses, but of course, family comes first. As expected, Claudia was all in and even suggested we get a bottle of Champagne to toast with at midnight. Being in the middle of a pandemic, we needed outdoor activities, for safety reasons, and since it was late December, we also needed activities where we wouldn’t freeze our little tuckuses off. I’m not sure we succeeded with that second goal. 

As usual, I got a hotel with an early checkin (noon) and arrived fresh from the nail salon. Claudia arrived just as I was finishing my eye makeup. Oh yeah, sidebar: A few weeks ago I went to the eye doctor. I’m far sighted and very much need glasses to be able read anything. This makes eye makeup, to say the least, challenging. Basically, I put on eye liner by sense of touch and then put my glasses on to see how it turned out. So, at this recent visit I asked the eye doctor for contact lenses that would allow me to finally see while doing eye makeup. If you’re wondering, yes, I had to come out to her about my makeup motivation, because it’s an odd request. It’s odd because the contacts make me near sighted, so I additionally need near sighted glasses to be able to see at a distance. I got a cheap pair of those online for $25. It’s actually quite disorienting to need to take off my glasses to see up close and then put them back on to see far — completely the opposite of what I usually do. I’m not sure those contacts improved my makeup on that particular day, but it was definitely more deliberate, which suggests that improvements to my technique are on the way. I’m actually quite excited about the prospects. Maybe time to invest in some higher quality eye makeup brushes. 

About ten minutes after Claudia arrived, there was a knock at the door. It couldn’t have been Rubi, because she wasn’t scheduled to arrive for another few hours. Then I remembered that I invited my friend Juliana to stop by. She doesn’t go out, but we chat quite often online — she tends to keep me in check with all my crazy Julie schemes. On this day, we were doing an accessory swap — a red clutch purse of hers for a pair of heels I got for a steal on Black Friday. I actually used that purse on that very night — much smaller than I’m accustomed to (only room for a wallet, a phone and a lipstick), but I loved the feeling of that little square handle swinging on my finger all night.

After giving Juliana a peek at my evening outfit, I got dressed in my afternoon shopping outfit — houndstooth skirt, black top, black zigzag pattern tights and my new Nine West ankle boots — very chic. Juliana was on her way out, so I asked her for a ride to the Michigan Avenue Nordstrom’s — just a few blocks away, but nice for us to chat a bit along the way. I was going to Nordstrom’s to visit the alterations department. I’ve never had a dress altered before, but if I was gonna get pinned up correctly, I would definitely need to be in Julie mode. I thought about going some other day, in boy mode, but then I would need to bring hip pads and my padded bras in a backpack and it would get all kinds of complicated. This was definitely the right way to do it. Of the 3 dresses I brought, only one needed to be taken in. The other 2, only needed a second opinion that they already fit perfectly — silly Julie. 

My second objective for the afternoon was to look at glasses. The second benefit of the contact lenses is being able to experiment with more feminine frames, since near sighted lenses are rather cheap at least compared to my usual bifocals. Shopping for glasses on Michigan Avenue was definitely not the place to find cheap frames, but I figured why not start with high fashion to see what I like and maybe find something similar online. The sales associates were super friendly and helpful and seemed to be understanding of the fact that I wasn’t quite ready to buy yet. Got plenty of pictures of various frames for future reference, but I wish I had remembered to smile — maybe next time. The pic is of the pair I liked best, but at $399, definitely not in the cards.

The chosen but expensive glasses.

Got back to the room around 4:45. Claudia was almost ready, just had to do her nails, and Rubi, who arrived all ready to go, was waiting patiently. I touched up my makeup, mostly darkened my lips from a daytime nude to a deep dark red. Then, I changed my skirt to the black sparkly one and traded the ankle boots for knee boots — for warmth. I could have stuck with the black tights, but to add some extra pizzazz, I changed to fishnets with nude dance tights underneath — again for warmth. Also, added some giant super sparkly earrings that I had picked up the day before at Nordstrom’s Rack — I have a lot of trouble getting out of that store without buying some sort of jewelry. Added Juliana’s red purse for a pop of color and topped it all off with my long black coat (Ooo, that reminds me of this song. Oh wait, I still needed a mask. The boy me has one mask for every occasion — Julie has almost a dozen. The sparkly mask that was too hot in the summer was perfect for tonight, both for the weather and the theme.

We were out the door by 5:15 for our 5:30 reservation — in the age of Covid, everything is pushed earlier, because everything closes by 10 or 11. It was a nice short walk across the river to a place called Raised. It’s a rooftop bar on the 3rd floor of a hotel with magnificent views of the skyline along the Chicago river. Our arrival was met with a warm, “Welcome Ladies” and we were escorted to a group of couches surrounding a gas fire pit — very swanky indeed. While the fire wasn’t warm enough for us to take off our coats, it was enough for us to enjoy some drinks and scrumptious appetizers.

There was a 90 minute seating limit, so our next stop was the riverwalk to see the 7 p.m. showing of Art on the Mart — a show where the Art Institute projects images of classic paintings on in the massive Merchandise Mart Building — at one time this was the largest building in the world. It was pretty cool and definitely worth the short walk over. After the show, we, of course, took the opportunity to snap more than a few pics.

From the riverwalk, it was a short walk to the train and just 2 stops to the West Loop where we were headed to a place called Federales, just steps from the train station. I expected we would be sitting out on their spacious patio, under heat lamps, but the very welcoming host brought us inside. I couldn’t figure out why it was so cold in there, but then noticed the retractable roof. We got some awesome tacos, had a few drinks, talked it up with our server and finally decided that we were too cold to stick it out any longer. It was a great place and we were sorry to leave — we’ll definitely be back under warmer conditions. The issue was that 4 hours of continuous coldness was taking its toll and the fun was beginning to fade. So, we called for an Uber and headed back to the hotel. 

Just before heading up to the room, I remembered the restaurant across the street — a place called Parlor Pizza that we had looked in to, but didn’t make it on our agenda. Rubi and Claudia were leery, but I promised that it would be for just one last drink. This place had a kind of tent set up on the sidewalk with those flame tubes you’ve probably seen around. Ahh . . . so much warmer than the other two places. We definitely should have had this place on our original agenda. 

After our one drink and a quite a bit of chatting we finally made our way up to the room. It was about 10:30 and we were all completely exhausted — being out in the cold burns more calories than one would expect. So, in the true style of a couple of 50 year old broads, Claudia and I agreed that the New York midnight (11 p.m. Chicago) was when we were gonna pop the Champagne and toast our Faux New Year Celebration. By 12:30 I was passed out in one bed, Rubi in the other and poor Claudia was left to deconstruct by herself before heading home — yeah, one of the rare occasions where I got to actually spend the night in my hotel room. 

All in all, it was a great night. Although a bit cold, I’ll take what I can get in this age of Covid. I think the best part was our Faux NYE theme. Even if we didn’t exactly make it to midnight, the sparkly outfits put a celebratory air to the night. I think I’m seeing a burgeoning tradition here. One that might blossom into a larger group in the future. I guess we’ll see if Julie can pull such a thing together for next year.

Tags: crossdressing, featured, Out & About

Category: crossdressing, Out & About