30 Days of Dressing Intentionally
Returning to the office highlighted just how frumpy I had become. I would try on several variations of garment combinations and still, nothing would feel right. And even when I managed to put together an ensemble that looked polished, I wouldn’t feel like me.
I’m writing this in the past tense, but it is an ongoing problem.
In August, I shared my recent thrift inspiration, and really, these vloggers have helped me be more intentional in general. Following in Hannah’s footsteps, I decided to give myself a 30 day challenge and follow her planning tips. Every day in September I would give my full effort and intentionality to what I wore. And not just on the days I go into the office or meet up with friends, but on my errand days, on my lazy days, on my work from home days, I would give 100% into my outfit choices. Below, I detail my approach and the results.
start the night before
It can be hard to be intentional when the work-day countdown is on. So taking a little time before bed to pull out a few outfits that were on my mind was crucial to not making a rushed decision. I could think about the weather, my calendar (would I be walking anywhere?), any after hours social engagements, and all the other factors that go into choosing my fit thoroughly. I tried pairing different pieces and testing out belts, shoes, and jackets ahead of time without the pressure of being late. It was liberating. Most nights, I would have my outfit selected and set out before going to bed.
find visual inspiration
Using Pinterest to gather outfit ideas, especially ones that include pieces similar to items I already have, was incredibly helpful. I started a board for aspirational outfits and one that felt more realistic. I looked for combinations that used familiar articles of clothing that I knew I could replicate. This strategy helped me be excited about getting dressed and brought the play back into the process. And practically, it helped make my wardrobe feel fresh by pairing things that I may not have tried before.
Learn from flops
September 1 was the worst. I followed all the rules. I found an inspiration image that I liked, it matched my current wardrobe, I set it out the night before… I was starting strong. But throughout the day, something felt off. I wore a denim button down over a black maxi dress, nothing wild, but I just could not relax. A few hours in I felt too casual, so I buttoned the shirt all the way up. But by lunch, I felt stiff and tried tying it up at my waist. Then, I returned to the way I started and had it open but rolled up the sleeves. Nothing worked for me. I could not wait to get home and get the outfit off.
The next day went similarly. What worked in my head was not working on my body. So instead of just pulling the outfits out the night before, I started trying them on. Walking and sitting in them made a huge difference. I realized that some of my clothes had become worn over time or didn’t fit like they used to. So in my head I maintained an image of how they felt when they were new and it just didn’t reflect the current condition or fit. This process actually helped me prune parts of my wardrobe.
Identify Patterns
By the end of September, some patterns emerged. For dresses, I felt most comfortable toning them down with sneakers and a denim jacket. It was adaptable to climate, easy for a lunch-time walk, and still nice-looking enough for the office but not too nice I felt too stiff to meet with friends.
Though I’m still refining my approach to skirts and pants, after this 30 day effort, I feel much more comfortable reaching for certain pairings. But the journey continues.
Though work was my most frequent setting where this initiative mattered, I put intentionality into even the most casual of settings. From jogging on the beltline to the Shakey Knees music festival, I took time to find something that was comfortable and made me feel confident. As Hannah says, “you’re getting dressed either way.” Might as well make it something I look and feel good in.
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