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It’s not all plaid.

This week was a bit of a whirlwind. It’s not just the sudden drop in temperature; it’s also the upcoming eclipse on the 14th and the new moon in Libra that’s adding a touch of unease to the atmosphere. Changing seasons always bring a mix of nostalgia and anticipation. For me, it’s a trip to my time as a student. Back in school, the beginning of fall always filled me with excitement. I adored being a student, with my color-coordinated notes on my iPad, diving into class novels, sneaking in library lunches, and aimlessly wandering around campus. But now it’s also got me thinking about the future – will I look back next fall and remember writing this blog post in my cozy bedroom? Will I be nostalgic for this moment too?

Still, this week has been strange for me. First, I was in no mood to dress up. The weather has been all over the place, swinging from 40 to 60 degrees on a good day. My wardrobe is stuck in a weird, in-between phase, clinging onto summer while the leaves are turning. I found myself daydreaming of outfits that would rekindle my inspiration, imagining myself taking a leisure walk through the streets of Chicago. Starting from the far south side, past the steel mills, and navigating through the daily chaos of people going to and from work. I pictured myself rocking… something plaid. 

Plaid and autumn are like a match made in heaven. But more importantly for me, it takes me back to my earliest educational memories. My Catholic School days — where I had a complicated relationship with that classic pattern. Back then, I hated it. It felt like a symbol of conformity and restraint, the embodiment of the school’s strict code of conduct. 

Now, as an adult with no uniform restrictions, I find myself drawn to plaid and skirts paired with stockings. Something that used to be restricting for me now excites me. It reminds me of life’s possibilities and how far I’ve come.

And pulling on those stockings triggers sweet memories of my mom. I remember how she used to apply pink lotion to my legs before helping me slip them on. I’d often be half-asleep during this routine, wishing for just a few more minutes of sleep. This process now holds a special place in my heart. 

This week, I had plans with a friend on Tuesday and a content meeting on Wednesday.

Tuesday I was feeling a bit sluggish, but I prevailed and matched my blue plaid skirt with a black lace top. I wasn’t sure how cold it would get so I opted for a fluffy white coat in case the temperature dropped again. I wondered if I should wear the white coat or a black coat with white frills. This decision took a while and I kept switching coats until I walked out the door.  I finally put on a pair of Ugg boots and made my way to meet my friend. At around 4:00 I noticed the weather went up to the 60s so I took off the coat and used it as a headrest on the train ride home. I should’ve worn the black coat, it was lighter. 

Wednesday came around and I had a meeting downtown. I went for a plaid dress because I wasn’t feeling like putting together a whole outfit. I needed some creative juices for this meeting and I wanted to feel writerly so I added the brown coat as an extra layer. Wednesday’s outfit felt a bit better than Tuesday’s outfit, but maybe that’s just because I gave myself less time to contemplate and just went with my gut. 

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