1) Strappy Sandals // Don't let the brisk temperatures stop you from wearing these babies.  When wearing a cocktail gown, you're going to want something other than pumps and these sandals fill that ticket. They come in a variety of colors and their simplicity lets all the attention go to the gown.

2) Pumps // These are the enormously popular MICHAEL Michael Kors Flex pumps. They're under $100 and come in a variety of colors, sizes, and widths. Yes, that's correct, you can get these in wide widths. 

3) Booties // I chose these booties because I'm in love with the bow on the back of them. I can wear them with a dress or pants and they come in a lovely brown shade.

4) Leopard print flats // I chose leopard print because it goes with a wide assortment of outfits, but a pair of printed shoes can help liven up your "blah day" outfit. 

5)  Basic flats // I loved the scallop details on this pair of flats, but having flats in at least a nude and a black can help cover a range of outfits. They're also handy for keeping in the car or bag in case of heel breakage or if you feet go on strike. If you wear flats almost every day like I do,  it's worth looking into buying a better pair than the cheapest special. I've developed tendinitis from wearing flats so now I have to spend more money on them which feels somewhat criminal to me but my feet don't holler at me like they used to.

6) Duck (Bean) boots // If you don't already have these in your mudroom, can you even call yourself a prep?

7) Loafers // Be it Weejun, tasseled, or with a riding bit, a loafer is hardly ever the wrong choice of shoe. Cordovan or burgundy is the preferred color choice but browns, navys, etc. aren't too far off the mark.  

8) Tall boots // These are best kept without much adornment. The boots pictured have wide-width calves, if want more information of boots, see my post on boot shafts of all sizes.

9) Sporty Sneaks // Hardly anyone dresses up for anything, anymore.

10) Driving Mocs // Driving mocs can be switched easily with loafers, just all-in-all a good casual shoe. They come in many bright colors so don't feel beholden to just stick with a neutral. Some people could also get away with the Minnetonka Kilty moccasin.