I like the chelsea style the best as well although I have been looking for a zip up pair preferable in some kind of rougher look or suede. My roomate has a pair of Saks labeled boots he got on clearance last year that are awesome but I can't find anywhere.
I just picked up a great pair of Alden's Cordovan Monkstraps. I love these as I can wear them with a suit for all but the most proper occasions but they work great with a blazer or just slacks as well. I also love the look of burgundy shoes with navy suits and I just got a new custome tailored navy pinstriped suit.
Also picked up several things from Gilt.com (hoping they fit): a pair of Ted Baker driving shoes, a great pair of Gant Cords and two pairs of John Varvatos cotton pants. I wanted a pair of drivers and had been looking for something on sale so that works great. Additionally have high hopes for the Varvatos pants as I already have one pair of microcords that are my most comfortable and best fitting pair of pants for casual wear.
Last thing I need is a new overcoat and raincoat. I am hoping to pick up a nice Khaki raincoat (probably from Brooks or J.Press) on sale and am trying to decide between the same for an overcoat or to get a custom one where I get my suits made.