Super Awesome Shopping Day 

(Click on the photos for a bigger image.)

If you’ve been following my posts, you’ll know that my last two outings were logistically challenged. So I was totally ready for something with much less stress — basically some light afternoon shopping followed by a low key dinner. Originally, I was planning for a solo day — again to minimize logistics — but a few days before I invited my Facebook friend Rubi to join for dinner. She’s from Chicago, but we had yet to meet in person. Turned out she had the entire day off, so I invited her to join for the shopping part as well. We were both excited “girls day” out shopping. 

I got a hotel room just a block from the Michigan Avenue shopping district and made dinner reservations at a restaurant across the street — no Ubers or long train rides on the agenda. I was able to get a nice early check in — 11:00 a.m. — although after dropping off my bags, I immediately went around the corner to the nail salon to get my 10 digits all prettied up. When Rubi arrived I was just finishing up my transformation and we were out the door by 3:00 p.m. My primary goal for the day was to be a Mag Mile fashionista and walk into those high class stores like I owned the place. 

Daytime attire.

Let’s take a step back and review my afternoon outfit. Started out with my long sleeve black bodysuit top from NY&Co, always a good starting point. Had a few skirt options, but went with the red/black plaid pencil skirt from Macy’s. Added some cute ankle boots ($20 from somewhere I can’t remember) — a very chic look I’ve been wanting to try for some time. Had planned on wearing black tights, but it was 55 degrees and sunny, so I figured I could go bare legged and be a little cooler in the stores — also more typical of what a fashionista would wear. Finished the outfit off with my long black coat (a great November look) along with my black Kate Spade purse. Oh yeah, did you notice the new wig? It’s a long bob (aka a lob) with dark roots — I think all my other wigs just got demoted.

Our first stop was Ann Taylor. I had bought the blush print dress online and scheduled for an in-store pickup — no shipping charge and the bonus of getting to try it on in Julie mode. At 75% off — $30 total — I think it’s definitely a winner. Now, I just gotta figure out where to wear it. Pro tip for a shopping day: bring a pair of pumps in your purse for trying on dresses. If you look closely over my shoulder, you’ll find Rubi in the mirror, along with my backside — I’d share a pic of the two of us, but it seems we didn’t get a good one of us together.

(L.) At Ann Taylor. (Middle) At Nordstrom. (R) The dress Julie was thinking of trading in.

After Ann Taylor we made a quick stop at Sephora — didn’t buy anything, but did seriously consider some new makeup brushes. We, then, went across the street to The Gap to see if I could figure out some jeans for next summer. After a conversation with the sales associate, I tried on the boyfriend and the girlfriend jeans. I’ve already got a couple pair of skinny jeans, so I was looking for a looser fit that wouldn’t be so hot in the summer. Settled on some girlfriend jeans, but I wasn’t sure given the price, so I asked if there was a sale going on. Turns out they were 40% off, so I took the plunge. A couple weeks later and after trying them on a couple more times, I decided I didn’t actually like them and was ready to take them back. On a lark, I figured I would offer them to my wife. This is a risk, because if they are too big, I feel fat, and if too small, I’m in big trouble. She tried them on — they fit perfectly — and she was like, sure I could use some new basic jeans. Actually, that was the first time she’s accepted anything I’ve offered, which was great cuz it saved me a trip back to the store. Okay, back to the story. 

On the short walk over to the North Bridge Mall, I got a call from my daughter about her going to Target with her friends. We talked about logistics (there’s that word again) and if all her HW was done. All was clear, so I sent her on her way. Kinda weird being in full Julie mode and having regular dad conversations — not the first time and probably not the last. At the mall, I directed Rubi to White House-Black Market on the second floor. About a year earlier, I did another one of my ‘buy online, pickup in store’ options at that same location, which is why I remembered it’s location so well. That time, it was a red velvet skirt. I liked it so much, I wore it out of the store. However, on this particular day, we didn’t see anything that caught our eye enough to try on, much less consider buying. They did have some really nice jewelry and super cute sweaters, but kinda out of our price range. Oh, if you’re curious about the pick up in store thing and the name I give with the order, I use my boy name in case they require an ID. The sales associates have never made reference to it and in fact, will go out of their way to ask my name knowing that I’ll likely respond with something different than what’s on the order. If you’re concerned about doing it yourself, it really is a non-issue. Okay, back to the story.

The primary objective of going to this particular Michigan Avenue mall was to go to the Nordstrom’s and try on party dresses. Took a little while to find the right section, but when we did the sales lady was super helpful and quickly set each of us up with a fitting room — putting each of our selections in the room to eventually try on. I really love it when the sales folks make you feel like you’re getting the royal treatment. I stopped at 3 dresses and in the fitting room I started with the one I thought had the least potential.

(photo) Now, I wasn’t really intending on buy anything, cuz the prices there are crazy. But, I nearly fell in love with that first dress, the red spaghetti strap number. The other 2 were not even worth mentioning, but after those 2 I went back to the first, cuz I was mesmerized and wanted Rubi to get some additional pics with her good phone camera. I started scheming in my head about how I was gonna afford this dress. Back in May, I had bought a Nordstrom’s dress online (it was 70% off) and thought, “Maybe I could return that one and just pay the difference.” The last time I tried it on I remember thinking, “This is a ‘Mother of the Bride’ style. Is that what I really want to look like.” I actually had that dress back in the hotel room — just a block away — and it would have been feasible get it and close the deal that very night. I even had the sales associate look it up to see how much I paid for it. However, she suggested I wait and watch it online, cuz she was thinking it was gonna be going on sale pretty soon and they have plenty of inventory in my size. Plus, Black Friday was just around the corner. 

By that time, it was just about 6 o’clock giving us plenty of time to freshen up in the room before our 7:00 p.m. dinner reservation. Got back to the room and gave Rubi a warning that I was about to take off my wig and expose a quickly balding head. She was in the process of taking off her shoes and giving a long ahhhhh of relief. 3 full hours of nonstop shopping was more exhausting than we had expected. Took off my booties and after my own ahhhh moment, went to the bathroom to check my makeup — not too bad, setting spray was really holding up under all the mask wearing. All I needed was a little lipstick reapplication.

Then I remembered the Nordstrom’s dress and immediately wanted to see how it compared to the red spaghetti number. So, I pulled it out — the beaded navy number — and asked Rubi to snap a few more pics. Wowzzers! [Pictured above.] It was so much better looking than I remembered — way, way better than I remembered. Definitely not gonna be bringing back that dress. Gonna have to hope that the red dress goes on a sale. . .a super sale.

Day outfit upgraded to dinner attire.

It was getting close to seven, so I got re-dressed in the red plaid skirt, adding jet black hose and black suede knee boots — to be warmer for outdoor seating at dinner as well as glam things up a bit. The hostess and wait staff were super friendly and didn’t even bat an eye at either of us, even though my guy voice made my assigned gender at birth pretty clear. I had the salmon and asparagus while Rubi had pasta. We shared a tiramisu for dessert and gave a pandemic sized tip. Before heading out I made a visit to the little girl’s room and as usual found an opportunity to take a bunch of mirror selfies — the distressed mirror didn’t give much clarity, but it did give a cool vintage style vibe. 

We left the restaurant about 9:30. Pretty much everything was closed because of the recently imposed pandemic rules, which required all alcohol sales to end at 9:00 p.m. and restaurants to close by ten. So, we decided to just take a walk and found our way to the riverwalk. The Trump building is right there and I asked Rubi to get a picture of me giving it the finger. Probably not my finest moment and I don’t share the pic, because I’m in the process of trying to purge that *** from my existence — way too much energy has already been given to that black hole.

With the Wrigley Building.

We eventually ended up in front of the bright lights illuminating the Wrigley Building — Michigan Avenue and the river — a great place for some more pics. At one point, I was bending down, almost kneeling, to get a good picture angle of Rubi and I hear a cat call from a woman in a passing car. Not sure she was calling out to us, but I’ll take it, cuz it sure felt good.

The notorious mini.

Once back in the the room and after some more late night conversation, I remembered the super short sparkly skirt I had gotten at AKIRA, just before the pandemic — $5. The same day I bought it, I wore pretty much the same outfit, but with chestnut hair, to a swanky jazz club in Rodgers Park. Unfortunately, that night I didn’t get a proper picture, so I figured I should take advantage of Rubi’s good camera and the reasonable hotel room light. Actually, the skirt should be a little shorter than in that pic, because I think I was wearing it a little bit lower than it was intended to sit. 

The night finally came to an end and I volunteered to walk Rubi to her car — yes in that super short skirt, but with the long black coat — definitely a super sexy look, especially with those boots. After that, I deconstructed, took the train home (a fairly short trip) and finally got to bed about 3:00 a.m. 

Epilogue: Just today — about 3 weeks after that shopping day — that red dress from Nordstrom’s went on sale — 50% off. Needless to say, I’ve already scooped it up and am awaiting its arrival.

Tags: crossdressing, fashion, featured, shopping

Category: Out & About