It was time to put on my game face. Even though I hadn’t bothered to get ready for any sort of game in a decade.

Being a writer – more specifically a freelance journalist and blogger – had so many perks. No commute. No need for a car. No need to go down to the office. The office was just on the other side of the apartment – a desk in front of a window facing the street. My uniform was whatever I feel asleep in the night before. Clock-in time varied. Was I a rare “up-at-4-a.m.-every-morning” maniac or was I my normal “Don’t-call-Danielle-before-10-a.m.” Belton? None of it mattered because there was no boss to disappoint in my appearance or mannerisms.

It was glorious. But not all that great if you like A) people, B) to look nice and C) fresh air. But, hey, who wouldn’t give that up to avoid a subway ride or hours in gridlocked traffic?

The downside was that in my more than five years of office-less life I’d long stopped being any sort of fashionista. I was more of a “Comfortista.” For a while, this made sense, as I was so dedicated to getting my career jump started after leaving the newspaper industry. Who had time for clothes? But fast-forward to 2011 and suddenly my career was pushing me in a new, much more visible direction. I was working on a TV show that would eventually become BET’s new late night program with former CNN anchor T. J. Holmes. I was doing more press. And no longer was I living in my beloved Midwest where you can wear sweatpants and pajamas to the grocery store and no one blinks. (House shoes and a head scarf MIGHT get you a side-eye, but no one will actually say anything.) I was in the black bougie paradise of Washington, D.C. and now, working in Manhattan, N.Y.

Suddenly I felt really awkward in my outfit that said “this outfit is an afterthought.”

What’s weird is as a teen I was seriously into clothes. I had a look and everything. (It was the 90s. That look was a mix of Denise Huxtable, Mayim Balik’s Blossom, and Tia & Tamara Mowry’s Sista, Sista twin magic. Lots of kitschy vests and floral prints and floppy hats and combat boots.) And I was still pretty spiffy UP UNTIL about 2005-2006 when I hit the roughest patch of my Bipolar Disorder related-depression and spent a lot of time just trying to get up in the morning. Do my hair? Pick out an outfit? Who had time to think about that? I’m just trying not to give up on life.

So I was oddly starting at zero back in 2009 when I launched my big “Hey Everybody! I’m Stable Now And Ready To Rejoin Society” comeback. I had completely forgotten how to dress for my body type. I had no clue what was or wasn’t in style. The first outfit I purchased post-depression was a pair of skater punk multi-colored shoes from Target, black denim jeans, a long cable knit black cardigan sweater, and a black long-sleeved T-shirt. Of course, that was an outfit for the “uniform” I was required to wear when I was briefly a sweater folder at the Jamestown Mall Macy’s in Florissant, Mo. But, hey, the colored sneakers showed I had at least two-fashionable synapses firing … even if they were firing all in the wrong direction.

Did I like umpire waist dresses or A-line? Cargo shorts or pedal pushers? Baggy or fitted? Heels or flats? Like hell if I knew for about three years. I just tried everything. Failed about as much as I succeeded until finally, this summer, it all came together after I started a new workout and diet regime back in February this year. It’s funny what losing almost 30 lbs and watching a lot of AMC’s Mad Men will do for your fashion sense.

The main two things I had to do was:

  1. Embrace the shape I am and not what I wanted to be, and …
  2. Find a system and stick to it.

It drives me crazy when I think of the years I wasted as a teen and later an adult not dressing in the way that best suited my actual shape. I always loathed being curvy because I didn’t like all the gross attention I got from strange men, so I desired to be all elbows and knees like I’d been before puberty hit and turned me into a woman. And I tried to dress in that way, in that everything was two sizes too big or was sack-like in my attempts to cover up my big butt. But, as with anyone with a big butt, they’ve tried to minimize knows, covering it up only makes it look bigger.

So, I decided to take the good advice of my friend Toya in D.C. to embrace my giant butt and make it a featured guest star to my hair and face in my outfits. After all, what was worst? Having people think I was 30 lbs heavier than I was in trying to hide my ass, or wearing a form-fitting top that showed off that I had a small waist?

Finding a system was easier. That just involved accepting I had no desire to ever do my own hair and setting aside money in my monthly budget to get my hair done every two weeks. I’d already created a bunch of rules surrounding my hair (never cut it except to manage split ends, never put a perm in it again, etc.) Yet, I knew that as it grew and grew I had no desire to fight with it. That’s someone else’s job now.

Everything else was about “proper planning.”  I do TV a lot. So I needed to invest in decent make-up. Not just whatever came free with my one annual purchase at Clinique. I needed to relearn how to walk in heels. I needed to stand up straight. I needed to dedicate part of my brain to my appearance, even though there was a part of me that thought this was all a bit silly. But this wasn’t about what I thought was right or wrong as a person – this emphasis on looks over personality. I could be doubly invested in both. Especially when it was for the benefit of my self-esteem and professional career. I could lament on how much it blows that I keep moving to “lookist” places like New York and California, or I could take it on as a challenge and go for it.

Whatever discomfort is only for a little while. I’m still not quite where I want to be, but once I get there … I think we’ll all be able to tell.

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