The Queen of Cheap doesn't have to look that way

I'm starting to seismically shift how I present myself to the world, and I'm not sure if I'm fully comfortable with it yet.

I've always thought of myself as the Queen of Cheap (move over Tyra Banks). My wardrobe has consisted of disposable clearance rack purchases and the most unique items I could find at mass market stores like H&M or New York and Company. News of the next Payless BoGo sale is music to my ears. I love the feeling of buying something/anything so cute and trendy and seemingly one-of-a-kind, even though I always see other people wearing my "unique" clothes.

The most perfect example of this is the Bitten Houndstooth coat I got at Steve & Barry's for $8.88. I've since seen at least 15 chicks walking around Manhattan in this coat, and even on one chick I sat next to on NJ Transit! "I like your coat, heh heh heh."

So I've always bought cute things with the intention of wearing them for a season and then purchasing 20 of the latest new additions a few months later. Maybe it's living in Manhattan, surrounded by beautiful people and beautiful fashion, maybe it's that I'm getting older, and/or maybe it's because Tim Gunn just sounds so smart when he says a woman's wardrobe needs only 10 essential items...but I want to invest in good quality, beautiful, classic items of clothing that I can wear for years to come (or at least until I have children and will never again have the body I have now). And I'm starting! Just bought my first Diane Von Furstenberg dress, thanks to the Depression-fueled sale at Barney's.

So when I mentioned above that I'm not quite sure I'm ready to make these changes yet, it all comes down to my other deep-rooted theory about my image: That I don't want to look like I'm trying to hard, or look too good. You will NEVER see me with a cute outfit, flawlessly applied makeup, and coiffed hair. 2 out of the three, yes, but never all three. It's probably an insecurity--that if I put a lot of effort into my appearance and no one notices or suddenly no one thinks I'm attractive, that would SUCK. So I might as well do just enough that I feel good about myself, without feeling fake.

In the past I've never wanted to look my best or like I'm trying too hard to look good at work, because I never want other people to think I've achieved the success I've achieved because of how I look. I know this is becoming a more far-fetched idea now that I'm getting older, but it's something I'm grappling with.

But the more I work with men (and women) who compliment me when I look good and think I'm smart when I say something smart regardless of how I look, and the more I read things about the importance of image and business (i.e. Sarah Palin's extensive wardrobe budget, or this awesome article by Penelope Trunk. Of course I've used her advice about spending money on image when the economy is bad quite literally--take today's DVF and Louboutin puchase...) the more I'm trying to be more comfortable looking put together.

I've stepped up my game lately--just a little bit, by adding a few Anne Taylor pieces to my wardrobe (a store that just a year ago I would have been caught dead shopping in because it's for "old people"). And I think people are taking me more seriously. I've even been told by a coworker that they "like the new me", and I'm thinking, "oh wow, how craptastic was the old me?"

So I'm taking baby steps to overcoming this insecurity---literally! My stride in my new 4 inch heels is a lot shorter and wobblier than in my usual Payless ballet flats, haha.

I bet my boyfriend had no idea he would be one of the factors that started this whole transformation when he uttered the simple words "Want me to get you those shoes you like for your birthday?", and that my friend Melissa really got me thinking when she said "You need to be careful what you wear with those--you don't want your outfit to make people think your shoes are fake."

Basically I think this utterly superficial fashion transformation I'm undertaking is really about moving towards a new level of confidence and maturity and comfort in being a successful chick in her *gasp* late twenties...

Eh, maybe that's not too superficial after all.