A Night at Reggie’s 

My friend Niki was coming into town — stopping by on her way to The Detroit Invasion. Looking at our schedules, it turned out that the only day that worked for both of us was a Tuesday night. This wasn’t gonna be an all day thing, like last time Niki was in town, just dinner and some live entertainment. 

My first thought was blues — it’s been so long since I’ve seen some live blues. Unfortunately, in the entire city of Chicago, there was no live blues to be found on that night. Due to the ramping up after the pandemic most places were only open Wed-Sun. I found that the Green Mill (a legendary jazz club in Chicago) was open 7 days a week. But, the band playing that night specialized in ‘20s jazz, which reminded me of the music they pipe in at an amusement park — ya know, in the New Orleans Town part of the park. Green Mill is also, way up on the North Side, so it had two strikes against it.

On a lark, I decided to check out the Reggie’s website, cuz they have a rooftop bar and sometimes have acoustic bands play up there. Turns out they had an actual show going on that night with a band called Mr. Blotto. I had never heard of them, but they have this improvisational rock thing going on and apparently used to have a large following, cuz I keep running into people saying, “They’re still around, I loved that band back in the day.”

Reggie’s is nice and close and the music seemed good, so it looked like a slam dunk. Now, Reggie’s is not your usual music venue. It’s got very much of a punk rock/metal theme with graffiti all over the walls and Harley’s parked out front. I had been there before, but only once and that was for lunch with my daughter — never to see an actual show. So, I decided I would stop in a week before, in boy mode, and get a lay of the land. It was about what I expected, lots of black clothed people with tons of tattoos. My borderline office girl look that I usually wear was gonna stick out like a sore thumb. Thinking about my existing wardrobe, I had a number of options where I could have pulled off a great rocker girl look, but most of those involved knee boots and since it was July, that meant that I would need to do some quick shopping to find something workable. At this point, you might be thinking,”Tattoo covered Punk Rock Bikers? That doesn’t sound like a safe place for a couple of CDs to be hanging out.” But, if you think about it, those types of people would be appropriately classified as non-conformists and in my experience, non-conformists are exactly the type of people to welcome girls like us. 

There’s a store in Wicker Park called Ragstock where I remembered seeing some outfits that would be perfect. So, a few days later I made the trek out there. As I got off the train and was walking down Milwaukee Avenue, I remembered that there was a couple of wig shops on the way. So I stopped in — just to look around. Pretty quickly, I zeroed in on a couple of black ones. I don’t have a black wig, so I figured a $50 investment might be worth it. They were both kinda short, which would be good for July. I almost got the one with sharp bangs, which might have fit the bill for Reggie’s, but decided to go with my usual sweeping bangs style.

As a bit of an aside, you might have noticed that all of my wigs are side parted. The reason for that is because I feel like it frames my face to be more rounded and gives me a more feminine appearance. I’m of the opinion that it is impossible for a CD to pull off a center part — it elongates the face and highlights our more masculine facial features. Lots of folks recommend bangs, to hide our more prominent brow ridge. As you can tell, I’m not a fan of that approach and prefer to open up my forehead and highlight my redrawn brows, which I hope gives the feminine appearance I’m trying to achieve.

Okay, back to the wig store. Those stores usually have lots of cheap items all around the cash register. I’m completely unable to resist, so I ended up throwing in some eyelashes and a pair of giant earrings both for about $1.50. At Ragstock, I quickly found the skirt I had remembered, in a couple of different colors. In the fitting room, I found them to be a bit smaller and shorter that I wanted, but I was in a pinch and decided to go with the black and white, which actually went very well with my black and white Converse Allstars. I also tried on the wig in there, since the wig store didn’t allow me to try anything on due to pandemic rules. Standing in the very small fitting room, I could feel the outfit coming together. 

Black and white skirt with sneaks, and wedges on the right.

The next day, I had about a half an hour window to throw on some hip pads and test out a few options [add headless pics here]. The left one was my original vision. And then I thought, let me throw on some fishnets and give it a serious rocker look. Definitely did the trick. The wedges on the right I had just gotten in from an online purchase at Old Navy. They weren’t part of the plan, but they were also a good option — maybe a little serendipity. I sent these pics to a few friends and they were pretty much unanimous about the fishnet option being the leading contender. I should add that with that particular top, I was able to slide the skirt down below my natural waistline and give it a bit more length. The next time I wear that skirt, it’ll be probably be cooler weather and I’ll likely have knee boots, so a shorter skirt at my natural waist will be totally acceptable, especially if some hosiery is involved. 

A quick selfie before leaving the hotel.

On the big day, the weather could not have been any more uncooperative. The high that day was about 90 and the humidity was about what one would expect for Chicago in the summer. That meant that the fishnets were out and I decided go with the wedges because I figured that exposed toes would be cooler.

It was a short train ride from the hotel to Chinatown where we were meeting Coleen, Lana and Rubi for dinner. You already know Rubi from previous adventures. Coleen and Lana are regulars at the Wednesday meetups at Club Krave. Actually, Niki would be hanging out with them the next night. I’ve never been to Krave, cuz Wednesday’s are never good for me, but I did hang out with that group a couple years ago for a Sox game (LGBT night) — they’re definitely a lot of fun. Lana had suggested a cool Chinese restaurant next door to the Chinatown firehouse. Apparently, they play classic rock as background music. Sounded great to me, but when we arrived, we found that it too was closed on Tuesdays. So, we ended up at this hole in the wall kinda place where the menu said that we had to pay before being served — first time seeing anything like that. That didn’t happen and the food was better than expected. Another bonus was that the bill was way less than I had budgeted.

After dinner it was a short walk to Reggie’s. The front windows were wide open so there was basically no air conditioning, so we were lucky to find some seats under some half decent fans. Of course, we took plenty of opportunities to step outside and get some great pics.

It’s a little bit hard to tell from these pics, but the sign out front says, “We’re not happy til you’re not happy”. The band was great, although they might have been in too much of a Grateful Dead mood than we had expected. Rubi was in a fabulous mood and almost immediately made a beeline for the dance floor. This was the first time Lana, Coleen and Niki were meeting Rubi and they very much enjoyed her exuberance, which is one of my favorite things about Rubi. Took me a few drinks, but I eventually made it out to the dance floor to join her.

 At some point, we decided to head up to the rooftop bar in hopes of finding a bit of a breeze — as the evening temperatures dropped, the humidity kept increasing, which was not great in the bar, which had relatively little air movement. The rooftop bar was more crowded than I expected and there was a lack of music because an NBA playoff game was going on. We found a table, got a round of drinks, some fries and used the opportunity to talk a bit more. Most notably, I was able to get Lana to share with us her origin story, which is always an interesting topic for me. At some point, I put my name on the chalkboard to play pool. I thought it would be doubles and had Niki lined up as my partner. But, it was singles so when my name came up I had to play solo. Not that it would have mattered, because the guy I was up against was apparently the best player in the house and I got crushed. No worries, it was still fun. Coleen and Lana headed out at a reasonable hour and the three of us who remained headed back downstairs to catch the final Mr. Blotto set. They finished the night with a cover of Ramble On by Led Zeppelin. It was pretty awesome and I can see why they were so popular. On the way out, I picked up a Mr. Blotto t-shirt for my guy wardrobe. Rubi offered us a ride back to the hotel and when I suggested we get some last minute pics in front of the hotel, she was, of course, all for it.

Niki and Julie.

The hotel was just down the street from my place so it was definitely nice to have such a short walk home. While deconstructing Niki and I had a nice conversation about future plans — maybe we’ll be getting together again in September. We’ll see if it works out. In any case, you’ll likely hear about it at this same bat time on this same bat channel.

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Tags: crossdressing, featured, Out & About

Category: crossdressing, Out & About, Transgender Fun & Entertainment