Sperry Topsiders

Okay, I LOVE my Sperry’s. They’re perfect for trips to the library, running errands, and– obviously– regattas and practices.
A little Henley throwback
Well, I’m disappointed, and honestly a little horrified, at some of the shoes on the Sperry website right now.

Seriously, EW. Sperry’s are what they are today because they’re CLASSIC. Soccer Dad wore the same style of Sperry’s that I have when HE was in college. The current shoes…. shouldn’t be worn at all, especially not next season, let alone 30 years from now.
I get the whole “let’s expand the product line” marketing concept, but College Prepster is NOT a fan.

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This is terrifying. It was weird enough when girls on campus would wear the sneaker hybrid versions with sweats and socks, but ughhhh.


I totally agree. I've been wearing the same style of sperry's that my dad has had as well. They're classic! And go with absolutely anything.
But their purpose is to be CLASSIC, and timeless. I don't get it!! All I know is I'm perfectly content with my plain brown leather ones! 🙂


Agreeeeed. My dad wears the same ones he has worn (new pairs through the years) for like 25 years at least!!! They are the same style as the ones I wear, I have a tan pair and a blue pair.

The Preppy Princess

Ditto on the seriously awful. Have you seen the sequin ones? Hideous, simply awful. Those two words should never be used together: Sperry & sequins.

Sending you a smile,


I completely agree with you. Unfortunately, sometimes when preppy hidden treasures become too mainstream, they lose their extra glamour.

Also, I'm a fan of your blog! I just started my own, so please spread the would be much appreciated!!

class act


I was in the mall last weekend and saw a pair of HIGH TOP Sperrys. My jaw literally dropped and people had to walk around me due to my state of shock. Unbelievable!


I agree with the comments, bur do want a pair of the platinum color- they are not completey off the mark like the ones you showed!