A Tip For Developing Personal Style: One Thing At A Time

*trying out pastel tights in 2008
While in New York I had the opportunity to chat with a lot of friends and bloggers with fantastic personal style. With our shared interest in fashion it was natural that conversation often turned to clothes, style influences and development and so on. Often I was struck by how smartly dressed girls were in high school--from vintage prom dresses to a general self-confident and careless chic I've always admired and rarely been able to emulate. I'm a bit envious of women who knew themselves and their style early on. I didn't. I still feel as if I don't know myself most days. Much of my style progress has been documented on this blog as I only started to grow in confidence in college.
I discussed before how a wardrobe isn't built overnight and that it takes time to fill your closet with pieces you love, but how do you figure out what you love and what you've just been too afraid to try? I knew I had a desire to wear skirts and dresses, but was self-conscious of my legs for many years. When I started wearing skirts I still had to figure out what styles worked for me--would I be comfortable in a pencil skirt on a daily basis, or was a-line more my style? Even figuring out how to style my hair was something new to tackle and when I compared myself in jeans and a tee shirt to a vintage style blogger I admired who looked head-to-toe as if she had stepped out of the 1950s I was overwhelmed with the gap between who I admired and what I looked like. How did I find the right skirt, shoes, lipstick, style my hair--and still get to class on time? Perhaps other people can naturally make a leap from one style (or no style) to another, but it seemed overwhelming for me.
In the process of figuring things out I developed a little system: one thing at a time. More specifically, I challenged myself to try one new thing a week. I only had to wear the style for a single day that week if the project went poorly, but at the end of the week I still had to figure out a new "thing" to do. This also means developing a list of styles you enjoy or creating mood boards for inspiration. For example, one week I bought a pencil skirt and wore it for a full day without switching back to my comfort zone of jeans. That went rather well and the next week I made myself a thick headband ala Bardot in Les Mepris and winged my eyeliner. That went less well as I made the headband too small and had a headache by the end of the day, but the winged eyeliner became a signature for my style. I still wear my eyeliner like this every day. A week later I had to try out a different style I was afraid of. Over time I experimented with red lipstick, high heels, milkmaid braids, and through trial and error figured out what was "me" and what I admired more on others but didn't like on myself.
Everyone has their own style to developing a style (haha). Some people get to skip the "developing" part entirely either from disinterest or a lack of self-consciousness that means they make intuitive and bold choices from day one. Additionally, this system might be too formal or formulaic for some people, but it helped me. I find a complete overnight change frightening and I like structure; limiting myself to one thing a week kept me from being overwhelmed and motivated me to actively try new things. Like with food: we don't know what we like until we try it.


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