In the best and most appropriate way, Rob often reminds me to choose quality and timelessness over trendy and/or inexpensive. I sometimes forget this and get caught up in wanting the newest style of shirt or cut of dress and I almost always regret it. The items I wear regularly (and on which I am complimented most) are those that never go out of style and are high quality. A few pieces come immediately to mind: the Maria Dress from M.M. LaFleur, the best flats for work from AGL, and my Barbour Beadnell jacket.
With quality in mind, I've had my eye on a pair of Quoddy shoes for years, which are handmade in Maine. As they say on their site, "We work at wooden benches with leather, needle, thread, and a few basic shoes." The result is absolutely beautiful leather shoes, custom fit to your feet, that will last a lifetime. Because all of the women's shoes (and most of the men's) are made to order, I've hesitated to order because I feared they wouldn't fit, but a close reading of the customer service information states that they'll always let you return a shoe to be refit for you (and there are detailed instructions for sizing so hopefully all problems can be avoided).
My favorite shoes for women are the Ringboots (pictured below) and the Pennyloafers (pictured above). I can't decide if I could pull off the ringboots, but I'd like to think I could. The fun part of designing Quoddy shoes is that you control the look of the shoe down to the color of the thread with which they are stitched, the sole (type and color), and the type of hardware. I've designed two pairs of Ringboots below - check out the sheepskin lining on the pair on the left (how cozy).
I'm also coveting the Campadrille flats pictured above. Oprah magazine named them to its "15 American-Made Items we Love List" and the trouble really would be trying to choose a color combination. Quoddy also sells classic shoes for men that I could see Rob sporting. The Blucher is my personal favorite and a Classic Boat Shoe is always in style, even in land-locked Colorado.