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I love the classy denim on denim look. But I think maybe its best with shorts because then it isn't totally overwhelming.
Ever since I bought myself a sparkly cocktail ring at my sorority's charity jewelry show this December, I have become obsessed with cocktail rings. They dress up any outfit and add some unexpected "bling" besides the traditional necklace or bracelet. These are all from Kate Spade, and could work great with almost anything!

This adds a little bit of biker-chic to an outfit!

This one would look great with a vintage-inspired outfit!

You could use this to dress up an everyday outfit of maybe skinny jeans and a cute ruffled cardigan!
Horizontal stripes are one of those things you consistently hear about being a fashion "don't." But they can be very adorable and sailor-esque if you wear them with the right style!
JCrew is using lots of nautical stripes in their spring collection:
Tucked into a khaki skirt, cinched with a great belt.
I love how "Rêve" (French for Dream) helps to spice up this otherwise plain shirt. Speaking of French, this trend reminds me SO much of a French teacher I had who was très cute and would wear this shirt by St. James all the time!
If Jcrew isn't as on-the-verge as you want, you should check out their little sister store Madewell.
The striped shorts are an unexpected take on the trend, but the navy blue jacket keeps everything classic and nautical!
I love the mixture of a khaki, more industrial jacket with this dress. A little mix of toughness and sweetness is always a great idea!
Which version is your favorite?