Every few months I go through the arduous task of changing my clothing over to reflect the season we are in.

I go through my closet, pulling out stuff that is too summery for Fall and bring the longer sleeved shirts, dresses and tops to the front of my closet for more convenient access.  This process usually takes a few hours, mainly because I have tons of clothes. Way more clothing than any one person needs or could possibly wear in two lifetimes. Every season, I end up donating at least a 30-gallon garbage bag of clothing to a local woman-in-transition shelter but there are plenty of other garments that I have yet to part with. I have pants that I wear now and pants that I hope one day to fit into; dresses that have been in my closet since high school and shirts that I hold onto, hoping that they will come back in style – one day.   And don’t get me started on my shoe collection.  Imelda Marcos would be proud.

But even with my abundance of apparel, I have no clue how to put them together in a way that looks fashionable. I’m not totally fashion illiterate, like I don’t go out the house with missed matching colors – at least not all the time- or rocking 8-ball jackets and some stone washed jeans with the leather on the front, thinking I’m the Isht, or missed matching colors – at least not all the time. I do know how to wear a shirt, some slacks or a dress and look presentable. But that is as far as it goes. There are no extras like bangles and cute little headbands. Or funky colored and textured stockings or overcoats that just set the outfit off. When it comes to putting together fabulous, trend-setting ensembles like the cute girls in the Street Segment section of Essence magazine, I tend to look more like the blurry faces in the background.

There is fashion and then there is style. In my book, having style is more important. Style doesn’t require you to have lots of money or wearing expensive garments that you know on with your best paycheck, including the 10 hours of overtime, you just can’t afford – that is fashion. I mean, have you seen someone rocking a pair of Red Bottoms and the shoes are the only civilized part of their outfit? Style requires you know how to take that piece of fashion to look decent or smart. Some women I know can go to a thrift store and come out looking like a better dressed version of June Ambrose. Whereas I go to a thrift store and come out looking like I went to a damn thrift store.
I once asked one of my fashion forward friends how she does it. Giving me a sly grin she said, “I’ve spent most of my youth agonizing about the way I look. I was raised by my mom, who was very particular about how her children presented themselves. I’ve surrounded myself with books, magazines, television programs and friends, who have all help me to mature my style. For me, my style is the way that I express myself.” Cool, I asked her if she could mentor me so that I could discover my inner fashionista. She looked me up and down and said, with a sympathetic smile, “Honey, I think there is nothing wrong with the way you dress. Your style is a reflection of you. Some people are just plain.” To this day, I still take that as a back handed compliment.

But that doesn’t mean I don’t try. Three and a half years ago, I went to Europe, by way of Amsterdam. I noticed that all the residents and European tourist alike were walking around with some glamorized version of the parachute pants. You know, the extraneously baggy pants popularized by M.C. Hammer? Apparently they were all the rage in Europe and just a few days before my arrival, I had already started seeing glimpse of the return of the pants on a few celebrities. I thought this would be my shot. I snag a pair here and be among the first in my neighborhood to rock them. Those pants are still taking up space in my closet. I just never had the confidence to wear them. I guess my friend is right: some folks are just destined to be plain janes.

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• Is Ryan Gosling Singing Jodeci!? 9 White Celebrities And Their “Blackest” Moments

Dressed to the nines for the New York premiere of The Dark Knight Rises, Zoe Kravitz was looking very dark herself in this alluring black dress. With its sheer panels and ruched material, the dress covered her lady bits and stomach in a peek-a-boo manner, while the bottom of the dress showcased a black skirt that reached over the knee. On her feet were strapped heels with a sheer toe and strap over the foot, and in her hand was a small black leather clutch. This dress brought Kravitz a great opportunity to show off her new haircut (which I don’t think I’m feeling), but the dress itself is a no-no. It could have been a winner, but in certain places, the dress comes off looking cheap. The shoes are fly, the bag is cute, and she’s in great shape, but no thanks. Stop.

Know a celebrity whose style is so underwhelming it makes you upset? I’ve found myself looking at pictures of people I KNOW have good money but are dressed like they went on a shopping spree using the clearance rack in Rainbow. You don’t have to be dressed in the most expensive designer pieces, but hell, everyday people I catch on the subway dress nicer than some of these folks that parade in front of our televisions and computer screens daily.

But many celebrities start off on the tacky boat and somehow end up becoming young style mavericks. Practice makes perfect and everybody’s got to start somewhere, and that includes actress Kerry Washington. Homegirl was seen in leather pants and fur-collared turtlenecks when her acting career first started taking off, but now she’s killing the game with her sense of style. Our friends over at StyleBlazer compiled a photo gallery of some of her most interesting looks (yes, in a bad way) as well as her most recent A+ fits to showcase Kerry’s #winning and iconic style. Take notes folks!

To see the full picture gallery, click over to StyleBlazer.