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Wayfaring in the Windy City - Part One
A black jumpsuit with a cropped grey sweater and black heeled ankle boots is what I wore when flying to Chicago. The security was a breeze and the padded bra I wore didn't trigger alerts. This was the first time Prazia traveled with a dedicated checked in luggage of her own. The carry on fit all of my drab stuff while the personal item was a women's tote which sat nicely on the carry-on rollerboard. While walking to the gate which was far and seemed farther, thanks to 3 inch heeled boots, a woman walking behind me complimented on the tote purse. She was trying to figure the brand but didn't have reading glasses on so I told her and she asked if she could photograph the bag because she was looking for a new one. The crew member at the boarding gate was addressing everyone with the usual Mr or Miss followed by their last name, so just as she started saying "Thank you, M", I took happened to say "Thank you!" cheerfully and no Mr or Miss followed.
I could have taken a cab from O'Hare to downtown, but the train ride was only $5. The only inconvenience was dragging my luggage with one hand and 'his' carry-on with the tote on top with another. After about an hour, I made it to the station downtown which did not have an elevator. Imagine the sight of me carrying over a hundred pounds of luggage all at once upstairs two to three floors to the ground level. If you love your back, please do not attempt lifting heavy weights wearing heels. Fortunately, I didn't throw my back but the exhaustion was palpable.
Hotel check-in went smoothly. After catching my breath, I changed into a long sleeve fit & flare mini dress, touched up my makeup, put on some jewelry and my regular forms (I prefer smaller ones while flying and carried them in my tote through airport security), carried my tote on my elbow and a cross-body bag across and took a cab to the northern neighborhoods of Chicago. I had planned to visit two specific stores and a friendly bar and I hit all three before returning to the hotel room in three hours. On my bucket list was to have a proper sit-down restaurant dressed enfemme.
I wanted classy, so I went with an all black merino turtleneck and a charcoal pleated skirt, pairing them with a statement necklace piece and new sandals with mid height heels, a cloche hat and bracelet. The experience was priceless, right from the person who greeted and seated me, the server and the staff that refilled the glass with water. I ordered a salad with a filling side dish. The meal was satisfying and the lipstick stained the cloth napkin. The server took a few photos on my request. Two groups of women dining at adjacent tables left early, the men at the bar were classy and professional too and didn't stare but only looked for a brief second as they looked around, not all at once of course. I felt comfortable and I felt great the entire time. I tipped very well, it even caught the server my surprise.
I walked back to the hotel. A lot of you would know how it feels walking in new heels. It was painful, but the rewards were exponentially higher so I bore the pain with smile. A woman standing next to the Chicago Theater, likely theater staff, excitedly agreed to take a few pictures of me. As I set down my tote on the ground and was just taking off my coat to 'prepare' for the 'photoshoot', she took this photo.
