Right now is the time of year when overhauling feels like the norm. We’ve just gotten accustomed to summer officially ending, we’ve broken out a jacket or two (even if we have to shove them back in the closet on a rogue 80-degree day), and it feels like a time to get serious—whether that means laser-focusing on the goals we want to achieve before the end of the year or getting better informed to cast our vote in the midterm elections next month. No matter how you define it, reflecting and reevaluating can be an incredibly powerful—as well as challenging—task, and this inspired us to turn to real stories within our own Who What Wear community.
We asked you about undergoing a major style overhaul. For some, this might mean a loss of personal style, but for others, changing how we dress is more about taking a big step into a new chapter in our lives. Below, here’s what four women—including a very recognizable fashion insider—have to say about their journeys, in their own words.
“I have lived and worked in London, Hong Kong, Tokyo, and New York [as the former vice president of global buying at Net-a-Porter], and now, since 2017, I’m in Los Angeles, where I’m the chief brand officer of The Collected Group. It’s a totally different way of life here and not a traditional city as the others are. Angelenos have a casual and relaxed lifestyle, so with that, I am in jeans every day, as opposed to once or maybe twice a week as it was before I got here.
“I still choose to wear a button-down shirt with everything as I did before, and when the weather is cooler, I throw on a tailored jacket. That part hasn’t changed and remains part of my style identity, as I still love structure and form when I dress. As someone who coined the phrase for Net-a-Porter #dressfromthefeetup, all my shoes are now flat every day. It never feels quite right or natural in L.A. to wear a heel, somehow, for the life I lead day-to-day, and I’m okay with that.”
“It certainly makes me buy less, as the POV in L.A. doesn’t make you feel that you don’t need a huge amount of style options week to week. I tend to only review what I buy now based on where I am going to be traveling. And as soon as I’m back in Paris, London, or elsewhere, I’m back to the familiar routine of heels and dressing it up.”
“Living with sickle cell anemia has prepared me with the best self-confidence while battling with the complications of an invisible illness.
“My style slowly evolved as I began to recognize that I am bigger, better, and stronger than my illness. As a child, I started out wearing baggy pants and oversize shirts and hoodies to complement my depression and anxiety. But, as I’ve become older, I’ve been given opportunities to spread awareness and publicly speak about my battle with sickle cell. In addition to the positive transformation within my life, I have been able to donate my clothes to charitable causes and sell them, ultimately leading to an overhaul in my style.”
“My wardrobe consists of business attire with a mix of athleisure and minimalism. I get a lot of my style from the environment around me as well as inspiration from Hannah Bronfman, Eva Chen, and Briana Wilson of Matte Brand.
“Our clothes are a vital part of how we carry ourselves. I want people to acknowledge that I can still look radiant in my favorite booties, dressed head-to-toe in my most luxurious blazer and trousers, and still be a powerful woman beating sickle cell anemia.”
“I was born in Morocco, but I moved to Montréal almost 10 years ago. I always struggled with my style. I felt like I never knew what looked good on me and what didn’t. I still do sometimes, and I think everybody feels this way at one point (I hope). But for a long time, I didn’t mind. I went for cute clothes or outfits without paying much attention to how practical or comfortable the clothing was/is.
“I experimented a little, dying half of my hair turquoise and starting wearing different kinds of clothes, mostly bobo/grunge/rock. Then, during my first year as a master’s student, I cut my hair short and went to spend a month and a half in Paris during the summer. At that point, I still didn’t care about the way I dressed that much. I mostly spend my summer visiting museums and going to summer school. At the end of summer, I came back to Montréal to finish my master’s and cut my hair even shorter (thank you, Paris).
“And then, I turned 25. I graduated. It was winter. I couldn’t find a steady job, and mainly worked as a research assistant and tutor. I had no big plans, but I felt like I needed change. At the same time, I started thinking about my reflection in the mirror. I looked like a teenager. Have you ever watched the movie Never Been Kissed with Drew Barrymore? Well, I was Josie—at least, it felt like it. The problem was, with no money, traveling and buying new clothes were out of my budget. But I didn’t care. I went to thrift shops, and I started buying clothes from people on Facebook—eco-friendly style.”
“Six months later, I got accepted to do a ‘training in a workplace’ program in New York for a few months. I packed a big backpack containing 15 kilos [33 pounds] of new clothes recently acquired, my passport, my entire savings (plus some help from my family), and I left for the Big Apple.
“I live in Harlem now. I have a very casual style, kind of boho, but I go for practical and comfortable pieces of clothing now. I like to keep it simple. I still don’t know if this is the perfect style for me, but I sure feel more like myself, not in terms of looking like my age, because I still feel like a teenager, but more in terms of looking like the woman I am becoming. The woman I aspire to be.”
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“You see the shirt in that picture? If I was given that shirt four or five years ago, I would have refused to let it even come near my wardrobe. But now it is a completely different story. The last four years, basically much of senior year in high school and the four years of college, I dressed in a way that was expected of me, to impress someone who I cared deeply about, rather than dressing to make myself feel good.
“But somewhere around June, there was a spark of change that ignited a fire in me to completely change how I dressed. That spark was a buildup of many things. In my college life or career life, I realized I was sick of my major and had only done it because I was expected to be a lawyer. I dressed how an Indian student would dress: I did not wear anything too short or tight. There were times, such as family gathering, that I had to wear traditional wear, which consists of thigh-length tunics called kurta with jeans or leggings. I was not confident wearing shorts or tank tops; I thought I would not look good in them. The second reason for the spark of change was maybe more of my confident booster: I stopped waiting around for the guy I cared deeply about.”
“It is funny to me now, that for all this time, I was subconsciously dressing to impress people rather than making sure I myself was happy with what I was wearing. After all these realizations, I now have the confidence to wear bold patterns or find the body-positive love toward wearing shorts in the summer. I now love styling band T-shirts or concert merchandise as statement pieces when I wear suits or a simple leather jacket–and-jeans outfit. I also found the inner confidence to wear Indian traditional attire as well, that I had tucked away for the four years of college. I, of course, do not wear it every day, but whenever I do dress up in Indian wear, there is a certain jolt of energy that comes from within when donning the red lehenga skirt.
“Since my style overhaul, I have become much more confident in what I want to with my life; I became more consistent on my blog and Instagram because I want to show the me who is in love with each of her outfits.”
Up next, shop 27 little black dresses that are anything but basic.