When I’m working with clients, I like to hear a little bit of their history with style. If they’re frustrated with their clothes now, was there ever a time when they enjoyed fashion? What were their feelings towards clothes in high school? In college? Why is this even important? By seeing where you’ve been, you can see where you need to go next, and it's good to recognize that our style is constantly evolving through different seasons of our life. 

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As you can probably guess, I’ve always loved fashion, clothes, and getting dressed. Shopping was always my favorite pastime. As I've mentioned, my grandmother was one of my earliest style icons. I find that a lot of women are seriously influenced by how their mothers dressed or how their mothers thought they should dress. Interestingly, the only influence I got from my family (other than my grandmother) was that it wasn’t important to worry about what you wore or how you looked, and in fact, it was a negative thing. 

As an adolescent and young teenager, my style was whatever was “in" at the time. Later in high school, I started feeling the need to assert my individuality and entered a grunge phase. My goal was to look as different as possible from everyone else. When I got to college at the Oberlin Conservatory, everyone there was so “alternative" that they all looked the same and I rebelled again by dressing more conservatively. A friend of a friend described me as “that girl who wears business-y clothes”. I was always aware of trends and attempted to follow them as much as budget would allow.

This is a pretty important point, because usually the budget was only slightly more than zero. After grad school, I moved to Manhattan and did my best to keep up with the fashionistas there while living on $25K and wearing shoes I could walk miles in. I often felt extremely insecure about what I was wearing and more than a couple of times, stopped in a store on the way to work to buy something new because I was so unhappy with what I had. There was a lot of pressure there.

Along the way, I started to notice that certain things make me more self-conscious and uncomfortable and I began to avoid those things. I remember specifically in college buying a red shirt because I thought I "should" wear red (I'm a brunette, after all) and just admitting to myself after wearing it once or twice that I just didn't feel good in it.  

After moving to St. Louis and discovering the wealth of cheap clothing available at thrift stores, I continued to experiment. I thrifted items just to try. This was at the time that fashion blogs were just starting to take off and I tried out many, many different bloggers’ styles. I ended up with two wardrobe racks full of clothes in our basement. 

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At a certain point, I started to realize that I the more experimental I was, the more I worried about what other people thought and the more time and effort and energy I had to put into getting dressed. I often changed multiple times before finding something that I was comfortable in. I started to think that maybe I could appreciate all these different looks in a different way and didn't have to copy them on my physical body. I could just read the blogs, appreciate the fashion editorials and then just wear what I actually felt myself in. Like looking at art in a museum, you can appreciate it, but you don’t have to take it home.

I also realized that by focusing on budget, I was wearing things that I didn't necessarily like or feel good in, but bought because they were a bargain. 

There was a relief in realizing I didn't have to always be trying new things. I also realized I didn’t need to stick to traditional rules of what I should wear. I didn’t have to wear red because of my coloring. I didn’t have to wear full skirts because my bottom half is larger than my top half. Just because something was a bargain, didn't mean I should wear it. I can wear what I want to wear, and if that’s mostly black and oversized things, so be it. 

I started thinking about all of this because of a podcast I was listening to, Garance Dore's "Pardon My French". She was speaking with two other French women, Caroline de Maigret and Isabel Marant, about style. They all agreed that the older they got, the more confident they were about knowing what was for them, and about deciding NOT to try things by saying (in a French accent, mais bien sur) "No, that's not for me, thanks”.

How has your style story affected what you wear? Do you have a hard time separating what you’ve been told you should wear from what you actually want to wear? Has your style evolved and changed as you’ve aged? 

Work through all of these questions as you determine your personal style in my new ecourse, Making Space. Sign up below for info when the course is released.