Thanks everybody. This gives me some great ideas!
rachylou -- these are the ones for the look you suggest!
http://ecx.images-amazon.com/i.....UY695_.jpg
lisap -- I like the idea of doing the menswear thing. Closest fit in my closet now are Levis 501s jeans (women's version) , which I sized up on, so they do have a unisex slouchy look. Oh, and I just realized that my Lululemon Jet Crops might work for this too! I have lots of preppy cardigans, some even cashmere, so I can play with this. My two colored handbags are the smaller size I use on the weekends, but some would actually match my sneaks and I never thought of that.
Jewelry I struggle with. I wear the same subtle jewelry most days. But my MIL gifted me most of her lovely collection when she retired, and though it's different than my minimal jewelry style, I'd like to make use of it. Subject for another post I guess, whenever I have time to get some of those pieces out and start playing around.
Kari -- this is sort of I have done the two times I have worn the black and cream Sauconys to work, but with the other suggestions I could dress them up a bit more.
kellygirl -- A blazer was my first thought too, because 99% of my pants are jeans. I have black, dark teal, and cream blazers now. More Spring-like blazers are on my wishlist!