Fashion Lifestyle

The 30-Day Style Confidence Challenge

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On a recent episode of What Not to Wear, Stacy London said “Being afraid to do something, and then doing it anyway? That’s called courage.” This inspired me to create a little “program” to help me (and you!) become a little bit more courageous. The 30-Day Style Confidence Challenge is all about stepping out of your fashion comfort zone. I have gotten into the habit of wearing nearly the same thing every day: ballet flats, jeans, some type of sweater or shirt, hair in bun, plain makeup. There’s nothing wrong with these things, it’s just that I don’t feel as confident or empowered in these clothes as I would like to. Clothing/fashion should make you feel great about yourself. If it doesn’t, then maybe it is time for a change. That’s where I am. It’s time for me to break out of this rut forever.  Someone once told me that if you make a change and stick with it for one month, you’ll stick with it forever. So, the 30-day challenge goes like this: Pick some type of fashion/beauty trend or change that you’d like to make or are a little bit afraid to try. Do it every day for thirty days. I suspect that by the end of the month, we’ll experience a serious confidence boost, and who doesn’t love/want/need that? At the end of the month, if you are feeling ambitious, start another 30-day challenge. For example, this first month of the challenge for me is all about wearing high heels.

I usually wear heels in my outfit photos, and then switch into flats before I leave the house. It’s not that I’m afraid of wearing heels. I just don’t like to be uncomfortable. But, Stacy and Clinton say on WNTW that other people don’t look at you and think “Wow, she looks comfy.” They just think you look sloppy. Also, I’m really short, so I could use the height boost. Considering I live in the snow belt, wearing high heels every day in January may not be the safest idea…I can see the broken ankles now…but pain is beauty, right? For February, I’m thinking I may try one month of red lipstick. Other ideas for the year include 30 days of wearing my unruly hair down, 30 days of no jeans (gasp!), one month of no shopping (double gasp!), etc. If you would like to try out this challenge, send me an email ( or leave a comment with your idea for the 30-day challenge, and keep me updated with your progress. I hope that it really will serve as a way to help you (and me) feel more empowered, courageous, and confident.


  • Reply
    January 19, 2012 at 11:13 am

    Have you seen Kendi’s 30 for 30 challenge? You could do a version of this and just pick out your more adventurous items to remix.

    Kendi’s rules for the 30 for 30 challenge are here

    My more recent 30 for 30 outfits from my stint in the Summer are here


  • Reply
    January 17, 2012 at 10:13 pm

    I like the idea of “30 days challenge”! Love these pink beauties!!

  • Reply
    January 10, 2012 at 12:44 am

    I love your January style challenge! And your pretty pink shoes. I wear heels almost every day, so I agree it’s painful but I quite enjoy them anyway.

    You would totally rock a cooking blog and writing a cookbook. Can’t wait to read those.

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