2009 brought new style challenges my way — moving to Chicago was a fashion revelation. I get annoyed when those who don’t know better say that Chicago isn’t a fashionable city. Sure there are those who dress down 24/7 (Uggs and sweatpants. Why?) but striding around these downtown streets, there are many women and men who have encouraged me to step my game up. Chicago style doesn’t try too hard, it doesn’t scream “look at me, look at me!” It’s less shrill and more effortless. Thanks to items that I was lucky enough to review in 2009, I felt like I fit right in. These are my favorites from the areas of jewelry, clothing, accessories, and shoes.

1. Peace Images — what more can I say about Peace Images that I haven’t already said? I have never met Camille, but she is totally a friend in my head. Her jewelry is AMAZING. The quality, the look, the creativity – hats off to her, for real. I own a few “peaces” and plan to get more, and thankfully there’s a neverending flow of new items debuting on her Etsy page. Seriously – she is always working on something new, unique, and show stopping. Every time I wear her Coffey earrings, someone stops me to ask about them. Her work with chains is stunning — her shoe chains, body chains, ear chains, joined rings… super fly. And now, for my ladies with locs or twists — hair chains. HOW FLY is this hair accessory?? And how fly is Camille? She’s got a blog now, too! Check her out!

2. Cut It Out apparel. A teeshirt line with a message and a vision that any afrobella would be proud to rock — can you dig it? I sure can! Cut It Out is the brainchild of Brooklyn-based bellas Tirinda & Noricia. Their teeshirts are high impact, inspiring, affordable, and of good quality. I’m proud to rock my Grace Jones homage tee in the summer, and now in the fall layered over a long sleeved tee. I’m excited to see what’s next in store for Cut It Out. Wearable homages to some afrobella inspirations, perhaps?

3. MBT Goti boots. My first encounter with MBT shoes came this fall, as my husband and I were strolling down Michigan Avenue. We passed some kind of orthopedic medical supply store, and I saw a sign for shoes that promised to solve knee and back problems, relieve neck tension, and do all kinds of other marvelous things. I tried them on and walked around the store. These round-bottomed shoes feel crazy at first, but I was immediately intrigued and knew I had to wear them for a longer time to try them out. I got that opportunity this December, and I gotta say — the Goti boots are the coolest-looking MBT’s out there, in my opinion. My only complaint with these boots — they’re a little tight for bellas with large calves. And the zipper looks cool, but I totally got it stuck and couldn’t get my boot off for an hour recently. A bigger, more finger-friendly zipper would be awesome. But despite those minor flaws, I LOVE these boots. They’re funky and attractive in a unique way, and SO comfortable to walk in. When I wear them I feel aware of my posture becoming straighter, and my super-flat feet which sometimes get achy, feel amazing in these. I wear them all the time. It’s enough to make me almost overlook the hideousness of the other pairs, just to have a pair to wear in warmer weather. Almost.

19. Um, Coach. That is all. The biggest giveaway I’ve ever hosted. Coach included me in their Holiday Blog-a-Day, and gifted me with a purse. The prettiest purse ever. I just want to pet it and hug it and call it George. Instead I only take it out for the most special of occasions when I want to feel uberglam.

20. Not Your Daughter’s Jeans. These were my fashion staples all year long. I initially bought my usual size, but I noticed they stretched out. Then when I went to Chicago’s fabulous plus size boutique Viva La Femme, and they clued me in — get one size down. I got me a pair of fly bootcut gray jeans that streamline and enhance my curves in the best possible way. I wear them everywhere. And my next pair of jeans will probably be a pair of NYDJ’s. But I’ve got my eye on those Cookie Johnson’s!

So that’s the best in style. One more category and I can finally move into 2010! Did you make any amazing fashion discoveries this year?

My Caribbean people will recognize the above from Barbadian calypsonian Gabby’s hit song, but it’s taken on a whole new meaning for me as the weather gets colder.

For real, my cute little ballet flats aren’t gonna cut it anymore in this weather.

Currently I have two pairs of boots, and I’m definitely looking for more.

I’ve been stomping the streets of Chitown in my Knot-Tie Ankle Boots, courtesy of Silhouettes. They’re comfortable, stylish, flat (which is very important for me, with my flat-as-a-board feetsies) and be dressed up or down. I’ve worn these with a little black dress and tights, and I’ve worn em with jeans. They look chic with both! I’ve got my eye on those Double Buckle Sport Boots, too!

I was looking for a cold-weather knee high boot that could keep my feet dry and warm while still looking fly with jeans. Also, I have plus size calves (to support my fabulous plus size body, hello) and I need boots that fit comfortably. Most leather zip-up boots don’t do the job.

I found what I was looking for last week at Bloomingdales! But they’re not on their website for some reason… so here’s a link. My salesfriend at Bloomies (shout out to Danielle!) got a real vibe for what I needed, and clued me into Pajar. She says these boots are known for lasting a long time and withstanding the elements amazingly. They fit like a dream, are made of all man-made materials (no fur for me, thanks!) and cost less than $200! SOLD!

Because of my foot-related issues, I can’t afford to mess around with a pair of boots that are purely fashionable. I need boots that are flat, fly, and functional. Boots that I’ll want to wear regardless of season, that feel good and reflect my funky fashion sensibilities. So right now I’m seriously contemplating investing in a pair of iconic Dr. Martens 14-eye boots. My husband swears by his Dr. Martens, and I know they last forever. The other shoes I’m looking at prefer to be known as “anti shoes.”

The MBT Goti boots have a clunky, funky, retro-futuristic Tank Girl kind of pizzazz, and I’d work them with pride.

MBT stands for Masai Barefoot Technology — the shoes have a curved sole and “activate your muscles instead of undermining them.” Hmmm. I’ve read blog posts that sound a cautionary note, but my curiosity continues unabated. I tried on a pair of MBT’s recently and absolutely loved the sensation as I strolled around the store. But are they comfortable for like, a day of walking around the city and going up and down subway stairs? I wanna know. If you’ve worn a pair of these – leave me a comment and let me know if they’re worth the money!

Those are the boots currently on my radar. They’re not the all-the-rage stiletto heeled over-the-knee variety, but I gotta think of comfort first – because if I’m not comfortable, I don’t feel at my most attractive anyway.

I’ll work on another post for you footwear fiends — all about boots for gals with calves like mine! What kind of boots are you buying for the holidays?