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I go to a private high school in the Mid-West and girls wearing plaid shirts and Uggs populate the place (sounds dreadful, but I DO live in the Mid-West), but recently I`ve been noticing that boat shoes are becoming increasingly popular every year. In my opinion Sperrys do look better with plaid skirts than Ugg boots, so I`m not complaining. I bought my first pair last year, and the first thing I noticed was that they were extremely comfortable, which is a big factor for me when buying shoes. I personally find them aesthetically pleasing, but I can understand why some people do not. There is numerous designs and colors of Sperrys for everyone`s tastes, ranging from sequin covered to stripped ones. Also, the brand Milly teamed up with them to create several new designs. If boat shoes are not your thing, then check out their flats and cute wedges they now have. I would rate Sperrys and 8/10. They are a tad costly (the cost is about $80 a pair) and some of the designs are not as comfortable as the leather ones. If you do like them, ask Santa for a pair next Christmas.