Preppy Footwear

Of course, no outfit is complete without proper footwear.  I've decided to provide a list of the best preppy shoes.  Different shoes go with different outfits and colors, but the best kinds are the ones that will go with most anything.

 The ultimate preppy shoe will always be the top-sider boat shoe, made famous by Sperry (pictured left).  There have been many cheap knock offs such as Island Surf, but Sperry's are the real top-siders.  Their classic brown color means they can go with just about any outfit, be it formal or casual, although too formal will warrant something more dressy, such as wingtips.  They were originally designed to be worn on boats.  It stands to reason that if your dad just spent half a million dollars on a boat, he's not going to want you marking up the deck with your shoes.  Thanks to the non-marking souls of top-siders though, that problem has ceased to exist.  They come in many colors, but with shoes like these, you really can't go wrong.  Sperry's can even be found at J Crew, a store that doesn't always carry products from different labels.

H.G. Bass also features a line of good boat shoes, but their most notable creation is the Weejun Penny Loafer (pictures right).  Although more formal than top-siders, Weejuns can also go with most outfits, although black may be too formal for casual occasions.  Brown weejuns tend to go better with most things.  These shoes come in many colors and patterns, from the classic solid colors such as brown and black to more daring patterns such as stripped, denim, or even plaid.  Plaid weejuns are great shoes (I own a pair myself) although they can be difficult to match with certain shirts and pants or shorts.  That said, If you want an eye catching shoes, there's no better model out there.  Anyone who ever watched "Mr. Rogers" may recall that the star of that shoe wore Penny Loafers.  These shoes were popular in the 1970's but thanks to Bass, their making a come back.  As a side note, if you walk around with an actual penny in the front compartment, it won't fall out.  I know from experience.  The ultimate formal shoe will always be the wingtop, though.

Of course, some occasions call for sneakers, and that's where Keds come in.  These shoes were popular in the 1940's and afterwards, but now their making, or have made a comeback, which is great.  Keds look good, and their comfortable, fine for most casual athletic activity.  Vans, which are similar to Keds and come in more colors, are also acceptable, and they are
even available at J Crew (pictured below).