Issue 50. I re-created a stranger's outfit from beanie to boot

And challenged some style assumptions in the process

I’ve made a lot of progress over the years to pay attention to my style intuition. As in, this newsletter focuses entirely on shopping and dressing according to feeling! AND, while running errands recently, a stranger’s outfit stopped me in my tracks.

The outfit was equal parts relatable, practical, and stylish. I’m pretty sure my jaw actually dropped. I didn’t take a photo, but I did compliment her, inquire about her jacket, and try to burn the outfit into my memory.

Typically, this would be the end of it. I’d say “that’s nice for her, I’m gonna do me.” Instead, I became ensconced with the idea of replicating the outfit as an experiment.

I typically would accept the feeling and move on, if getting dressed in my own closet was easy. During my Project 333 last autumn, getting dressed was really easy, no lie!

Something about the transition from autumn to winter has been tricky though. Here’s what I’ve noticed:

• Only one of my “real” pants is working for this season: I accidentally put my favorite dark-denim gap jeans in the dryer and shrank them slightly, so getting them to stretch back out has been a process. The Everlane ecru pants I purchased in December stretch out multiple inches, such that they practically fall off by the end of the day (I’m not a belt-wearer). Lastly, my light-wash, lightweight Gap jeans are not the vibe in 40 degree or rainy weather. As a result, I’m wearing my flared Lululemon leggings on repeat. While I love these specific leggings, the lack of variety is draining.

• I only have one cozy pull-over sweater: I still haven’t found a replacement for the striped cashmere sweater I sold last fall (this striped sweater is my only regret declutter in recent memory). As a result, my & Other Stories sweater is worn waaay too often.

• None of my boots are well-suited for wet weather, so I’m wearing sneakers everywhere: I’ve prioritized style over practicality, what can I say?

So, when I saw this person looking so put-together on a cold, wet day, I felt an overwhelming desire to literally re-create her look. What do I have to lose?

Here’s what I remember:

• Slightly oversized charcoal gray turtleneck sweater (obviously high-quality, probably cashmere)

• Kelly green, ribbed cashmere beanie (so luxe!)

• Uniqlo off-white puffer coat done up to the top

• Mid-wash 90s straight leg jeans down to the ankle-bone

• Black wedge bootie, clearly waterproof and very low-profile (not typically my style, but with the rest of the fit, just worked)

• Black Baggu Nylon bag, which I decided to omit, because I think would have liked the outfit without the bag, too

I had already identified that getting dressed had gotten hard. Creating a new outfit formula that worked for my daily life seemed totally appropriate.

So, I decided to go for it.

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Now, the main thing I wasn’t sure about were the colors involved in the original outfit: I don’t include either Kelly green nor black in my wardrobe, and I didn’t want the color to skew my perspective on the outfit as a whole. But also, what if the outfit was only good because of the color?? So, I decided to try out two versions. Any good experiment has multiple trials!

• Trial A—Copy the outfit head-to-toe, including colors that I don’t typically wear (Kelly green, black)

• Trial B—Copy just the silhouette, and tweak the colors to my typical palette (brown, blue, white)

• Trial C—Reimagine with my own clothing