Hello,

I've been reading the forums/blog for a while and am slowly starting to figure out how to dress. My workplace is extremely casual and also male-dominated, for reference, imagine that I work with a bunch of programmers. I've been living in jeans/t-shirts since high school and now that I'm 30, I feel it makes me look less professional/mature/capable.

I don't know enough yet to categorize my style. While I'm mostly a casual dresser, I do throw in the occasional flamboyant outfit/color. I have brown skin/black hair/brown eyes so I mostly wear black and intense colors (dark, deep, rich or bright). I have very few clothes that could fall into the pastel/white/light color category since they don't suit my skintone.

Sorry for the long intro, but wanted to provide context. I have some sports-related shoes and dress shoes, but here's my shoe wardrobe so far. I'm deliberately trying to buy shoes that are high quality and resoleable but also a little funky.

Black heeled boots bought last winter. I love these because they are very stable and I can run in them, but they also look good. They have 3 inch heels and are 4 hour shoes.

http://www.fluevog.com/code/?w.....ourID=2577

Brown heeled "fun" boots. On their way to me so I don't have them yet. This is my flamboyant side coming out.

http://www.endless.com/Eject%2.....B0025KVW1O

Red heeled Mary Janes for everyday shoes. These took a while to break in but they have become much more comfortable. 4 hour shoes but I'm hoping they will become 8 hour shoes.

http://www.fluevog.com/code/?w.....ourID=1784

I want to add one more knee high boot with a flat sole to the collection. This will be my "feet hurt too much for heels" + "wear with skinny jeans" boot. I don't intend to wear them with skirts - the other boots have that angle covered. I've decided on the Franco Sarto Pacayas, but can't pick a color.

http://youlookfab.com/store/20.....igh-boots/

Should I go with the chestnut or the black? I wear so much black, that black is the most practical color choice, but I don't need two pairs of black boots. The chestnut boots should be a different color/style from the other brown boots, but my wardrobe doesn't require two pairs of brown boots either. I did look for alternative colored boots but couldn't find anything as comfortable. The Pacayas felt amazing on my feet, so I'm really sold on acquiring a pair during the Black Friday sales.

I'm also looking for a black closed toe pump for dressy occasions with a 2-3 inch heel. It needs to be comfortable for an evening of walking and very stable. It will never be worn to work.. There is no rush to find this shoe, but suggestions are definitely welcomed.

That's going to be my total shoe wardrobe till spring/summer. For my lifestyle, I think this covers all my needs. Thanks in advance for your opinions and for reading this far.