Jazz, Spade, and the Case of The Missing Cardigan

At the jazz club.

It’s a Friday night and the band at the jazz club is just about finishing up. I had taken an Uber to the club, but since it’s only 11 p.m., I thought I might take the train back to the hotel. There’s a station just steps from the club, but it’s the wrong line and would require a transfer. To get to the station that doesn’t require a transfer, I’ll need to walk about 4-5 blocks. The walk is not such an issue, even though I’m wearing a new pair of heels — super cute suede Mary-Janes from Nine West. The real issue is that I’ll need to walk directly in front of my apartment building — something Julie has never done before. As I approach in my eye catching black and white polka dot skirt, I have the option of passing the building across the street. I decide to go for it, especially since the front of the building appears desolate. It’s a long building and about halfway past I see a couple of the maintenance guys — guys I definitely know — out talking on the sidewalk. As I walk past, they definitely notice me — how could they not? I try not to make eye contact and while I’m guessing I was clocked, I’m rather confident they didn’t recognize me as a resident. 

On the train.

The train ride was uneventful, except for the fact that I had to pee really bad by the time I got off — made for a very hasty walk from the train station to the hotel. My original plan had me staying the night in the hotel, so I could get an early start in the morning and have a full Julie day in the city. Of course shopping was on the schedule, but also some live music in the early afternoon at a cool rooftop bar, again not too far from my building. But, that all got nixed when my daughter’s weekend plans fell through, which meant that I would need to head home so I could take her to gymnastics the next day. It wasn’t really that big of a deal, because my friend from Milwaukee who had intended to join me for the weekend also had to cancel at the last minute. So, at least I wasn’t leaving her hanging for most of the day. 

After dropping off my daughter, I made it to the nail salon across from the hotel around 1:30. My nails were pretty long so they were looking really great with the understated milky white color I had selected. It was nice to get to the hotel and already be unpacked. The problem is that I had left the room as a disaster and needed to clear up some space for Claudia, who would be arriving in a couple hours. She arrived as I was just finishing my makeup and immediately sensed my less than stellar mood. Just explaining to her my disappointment with the falling through of my original plans put me back on track, in good spirits and in the right mindset to enjoy the remainder of the day.

Stripes and cold shoulders.

The weekend before, I had gotten the rare opportunity to dress at home, which gave me a chance to figure out what I would wear this particular weekend. It was expected to be unseasonably warm and I had a new cotton skirt that would be perfect for the weather. It’s white with multicolor horizontal stripes, but I had no idea what top to wear with it. Then, I remembered that I have a green cold shoulder top, which is super lightweight and one of my go to tops for warm weather. I tried it on and immediately knew it was perfect as the color matched exactly with the green stripes on the skirt. Before heading out for a little pre-dinner shopping, while Claudia got ready, she snapped a few pics of my full outfit. She insisted on getting a closeup, which turned out to be really, really great. 

The dress from Old Navy.

So, I hopped back on the train and was in the Loop in no time. I had planned to go to the Block-37 mall — it’s across the street from the State Street Macy’s, which I also planned to stop at because I had a gift card that was burning a hole in my Julie wallet. On the way, I noticed an Old Navy and on a whim decide to check it out — I’m always on the hunt for the perfect jeans, which are basically impossible to buy in boy mode, cuz I need hips to see if they actually work. I tried on a couple pairs, but they were a bust. I, then, noticed a cute summer dress. It was exactly what I’ve been looking for in a summer dress — light cotton material, not at all form fitting and a black and white floral print that could be dressy or casual. Didn’t even look at the price and was pleasantly surprised at the checkout to find it was only $12 — the earrings I grabbed in the checkout line were more than the dress. At Block-37, I went to the Banana Republic Factory store, which I had been to in boy mode a few weeks earlier, but didn’t find anything all that interesting — I kinda had $12 dress on my brain, so it was hard for them to compete. My walk through at Macy’s was about the same.

As a final stop, I headed over to Sephora — I know, dangerous to my wallet. Actually, I had been there the week before in boy mode. I was looking for some eyeshadow primer and found some for $10. But then, I remembered a few other things I needed and some other things I didn’t really need. Long story short, I was lucky to get out of there for only $120. But, this Sephora visit was much more targeted. The white skirt and blonde hair suggested that I needed a lighter color lip, which is different than the deep dark reds that dominate my little lipstick bag. The lightest color I had was this hot pink you can see in the closeup pic. It kinda worked, but I wasn’t really happy with it. So, I wanted to get a nude colored lip stain. (I’ve completely given up on traditional waxy lipsticks and only buy liquid lip stains now — they look much better and stay on all night. Especially, important now that masks are required in so many places.) I quickly found a color I liked and didn’t forget to get the matching lipliner. 

Back at the room, Claudia was finishing up and my other BFF, Jessica, had just arrived — having gotten ready at home. Due to the repeated on and off of the mask while shopping, the foundation on my upper lip and chin was in need of some serious touching up/replacement. This also gave the opportunity to try out my new nude lip color, which far exceeded my expectations. On the walk over to the restaurant, Jes mentioned the uncharacteristic lip color and we both agreed that it gave me a more natural look — a further step away from the overdressed CD that is my usual M.O.

While the white skirt outfit was super cute and I was looking totally hot, I started thinking it might be a bit much for our dinner plans. It was also rather form fitting and while shopping I was feeling a bit self-conscious about how it accentuated my small but noticeable belly. That combined with the indescribable feeling of wearing something you had just bought an hour before, motivated me to quickly change into my new $12 dress. 

OMG! I almost forgot to tell you about Kate Spade. About a week before, a random Facebook ad caught my attention — discounted Kate Spade purses. On a lark, I texted my friend Juliana and she was like, “the black one seems like the most practical, but the pink one is super cute”, which was exactly what I was thinking. Now, the discounted price was $90, which is about 3x what I would normally pay for a purse — usually I shop for purses at T.J. Maxx. She added that I should save my money and spend the difference on shoes. At that moment it hit me and I knew exactly what I needed to do. To capture the moment I’ll need to quote Col Kurtz: “It was like I was shot with a diamond . . . a diamond bullet right through my forehead. And I thought, my God . . . the genius of that! The genius! The will to do that!” I’ll start by saying that I’ve wanted a Kate Spade for a couple years, but was always afraid of the price — they usually run about $300+. Juliana’s comment reminded me that I’ve spent $80 on shoes before and didn’t think much of it along with the fact that I really don’t need any more shoes. So, I was very excited to text her back and report that I had just ordered both — the pink AND the black — and with 2-day shipping (for $15), they would arrive in time for this particular outing. You cannot imagine how pleased I am with these purses. I used the black one at the jazz club and the pink on the second day. My old black purse has no pockets and I’m constantly searching to find stuff. My old pink purse is better with pockets, but I still end up searching for things more often than not. The Kate Spades have exactly the pockets I need in exactly the right places, so I am never searching for the essentials, phone, wallet and cigarettes. In addition to function, the form is just to die for — super cute and oh so sophisticated. As an illustration of my love for these purses, just today, I worked out a new way of storing my purses, specifically so that those two are not sitting in a crumpled pile in the back of my closet. They’re standing up in a box so they don’t lose their original “perfectly cute” shape.

Okay, back to the story. Rather than hit up Boystown — our usual haunt — we decided to spend the evening in the West Loop/Fulton Market District. This is one of the more trendy areas of the city and pretty much dominated by cishet folks. Despite that, we were completely welcomed the entire night and I didn’t see a single person give us even a second look. Dinner was at this place called La Josie, which smack in the epicenter of the neighborhood. Our outdoor seating made it perfect for people watching — with all the trendy young people milling past, I got more than a few outfit ideas. Of course, the food and conversation was expectedly fabulous. After dinner we went to this bar called Recess, which has a massive patio surrounded by shipping containers — very sheik in an industrial kinda way. The crowd was again quite young and if the three of us (all 50+) were in boy mode, we would have been very much out of place. This is one of the things I like best about Julie mode — she is always more welcomed than the old, balding creepy dude that usually walks the streets of Chicago. After the bar closed (again at 11p.m., by city ordinance) we made our way back to the hotel for some late night conversation in the room before we all headed home. 

Epilogue: Saturday afternoon, I realized that I had lost my black cardigan the night before. I figured it must have fallen out of my purse the night before while I rushing up to the room, cuz as you remember I had to pee really bad. I was a little drunk, so it seemed very much plausible. Checking with the front desk, they couldn’t find it and I figured I must have dropped it between the train and the hotel. I was really bummed because it’s such a perfect sweater and goes with just about everything. On Sunday morning, it occurred to me that I probably left it at the jazz club — maybe left it hanging in restroom stall or on the back of my chair. So, that afternoon I went back in boy mode, found the girl who took my ticket the night before and she had it waiting for me behind the desk. As she gave it to me I could see a twinkle in her eye and I’m guessing she was thinking, “I would have never guessed you’re the same person.”

Epilogue 2: Danielle is the 4th of our little group, but couldn’t make it that weekend. However, the next Friday she was available, so her and Claudia decided to get together and ended up going to the same jazz club. That night I was home with the kids, so there was no possibility for Julie that night. But, once my wife got home from work, I walked up the block to join them for the end of the show and a few drinks at a bar across the street (by this time the mayor had relaxed the rules and bars are now allowed to stay open until 1 a.m.). I hadn’t seen Danielle since before the pandemic, so it was really great to catch up with her. While at the jazz club I had a chance to talk with the bartender that I had talked with the week before. Of course, he didn’t recognize me until I reminded him of the polka dot skirt. He was totally cool and we talked about bringing my son for one of the Sunday matinee shows — my son plays trombone and I’ve been wanting to get him to see some professional jazz musicians. That first Friday was my first time at this place, despite living a few blocks from it for over a decade. After these two visits, I’m planning to be back, and it might turn out to be the first place where I’m a regular in both Julie and boy mode — definitely would be new territory for me.

Tags: crossdressing, featured, Out & About

Category: Out & About