The Red Lipstick Chronicles

...or how I went from this:

June 2006

...to this:

May 2011

Needless to say it was a wee bit of a transition.  As a teen into my very early twenties I was obese, acne ridden, shy, wore no makeup and had a penchant for oversize black t-shirts and jeans.  I grew my blond hair out to the small of my back and wore bangs that made my overweight face look even rounder.  I loved lipstick but felt uncomfortable in it, almost always removing it as soon as I put it on.  I dyed my hair strawberry blond in high school but the red faded out almost immediately.  I just didn't have the resources to keep it up.  Makeup made me look a little better but it aggravated my acne so that I only wore it sporadically.  To this day I rarely wear more than eyebrow pencil, mascara and lipstick and when I do wear foundation its usually a tinted moisturizer.

Then I met Will and moved to Tucson.  The subsequent changes in my diet and exercise habits helped me drop 70 lbs gradually and kept them from coming back.  My acne went away.  My confidence increased and my naturally outgoing personality came out.  I ditched the bulky tees for retro inspired clothes, western shirts and began putting more care into my appearance.  I cut my hair off, too short, but I growing it out to my shoulders.  About a year ago the elements of my own personal style started coming together.

And the trigger was a Halloween costume!  Will had introduced me to the AMC show Mad Men earlier last year.  I went as Joan Holloway, he went as Don Draper.  I dyed my hair red, bought my first pair of clip on earrings and wore red lipstick and winged out black eyeliner.

 Will and I, Halloween 2010

Will and I, Halloween 2010

(Forgive the hair! It was too short for the style and the hairspray was starting to fail after too much bourbon and fresh air!)

I was hooked!

I felt sexy!  I felt strong!  I was compared to pinups and classic Hollywood starlets.  Quite a rush!  (Ironically, only two people recognized who I was supposed to be.  Oh well!)

While I don't dress as Joan on a daily basis (though I do show up at the coffee shop with a beehive from time to time, just for my regulars who are Mad Men fans!), some elements stuck.  The hair for instance.  I love being a redhead.  My blond hair was pretty, particularly when it went down my back, but my red feels more natural than my natural blond, for some reason.  People treat me differently too.  Instead of "Blondie" they call me "Red"; instead of being taken for a ditz, I am a fiery, sexy chick.  The earrings started a collection obsession that hasn't abated yet.  I've collected so many vintage earrings that I've had to start selling them.  And the red lips of course.  I now own a half dozen different shades of red lipstick and I wear it almost every day.  It makes me feel good about myself.  Happy.  Like I just had a bubble bath or treated myself to a bit of dark chocolate.

How did you discover your own personal sense of style?  Do you have a signature color or bit of makeup of clothing that makes you feel super special?