Why Did You Wear That: High and Dry
Written by: WhyDid | Why Did You Wear That?

Since it’s a miserable rainy day in New York today, I thought I’d dedicate this one to celebs and their rain boots.  Perhaps you don’t feel your chicest when strapping on your wellies, but after seeing some seriously stylish ladies parading around in theirs maybe you’ll change your mind. Hey, better than destroying your new suede OTK boots.


I believe Kate Moss was the first to make rain boots chic. Because that’s what Kate Moss does.


Gwyneth Paltrow in some serious lace up rain boots.

EXCLUSIVE: Hilary Duff Loves Vancouver! (And her mom!)

Hilary Duff with mom in Burberry rain boots.


Sarah Michelle Gellar in Hunter boots.


Nicole Richie in Hunter boots.


Ashley Olsen in Jimmy Choo for Hunter rain boots. (Does she know it’s kind of an oxymoron to be wearing sunglasses at the same time as rainboots?)

Last spring I wrote a little ditty on the Do’s and Don’ts of rainboots. Please review and stay dry!



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  • If you want to look good and stand out from the crowd, you need our WedgeWelly boots!

    Our Wellies are guaranteed to give you a height advantage over those flat Wellie wearers, and…………………. the high fashion surface patterns will make you the envy of everyone!!!!

    And if that’s not enough………………. these Wellies will be the most comfortable you will ever put on your feet (so if you’re planning long walks, make sure your feet are well looked after in our slipper inspired WedgeWellys!!).

    Rain rain go away, come back on a WedgeWelly day.

    Sarah xx

    Comment | December 15, 2009
  • Anne

    I ADORE my boots. Here in New York everybody wears them no matter the season!!! They are very trendy,lots of new designs…i hate it because i want them ALL!!! and they are very confortable!!!

    Comment | December 20, 2010
  • Mariana

    I personally think Ashley Olsen rocks her outfit with her sunglasses n rain boots, she’s not the only one doing it look at Nicole Richie, stop hateing!

    Comment | December 7, 2011
  • Hi Marlana,

    No hate here… I think Ashley is adorable. Just pointing out the obvious… if it’s raining, it’s not sunny. xx

    Comment | December 7, 2011
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