Confession: I don’t know how to wear sneakers

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True life: I’m not that great at casual wear.

I fully realized this a few months ago when two associates were shocked at how nice I look cleaned up. Apparently we’d only ever met in casual settings and when they saw me in my regular clothes it made a world of a difference. Of course I was mortified they’d developed a less than fashionable image of me but I can’t say I was completely shocked.

 

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Somewhere between high school and now I transformed from a t-shirt and jeans kind of girl to the woman who wears heels at a dive bar.  I can pick an outfit for a wedding in a flash, but it takes much longer to find a look for a relaxed outing. Are my open-toed Fendi stilettos too much for a street festival? Am I  doing the most in a leather skirt ? How can I manage to look simultaneously cute and comfortable like those girls in all the Coachella pics?

I’ve decided I can start to step my casual style up by investing in new kicks; more specifically  “J’s” as the sneakerheads would call them.

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As my first pair of fashionable sneakers in a while I’m playing it safe with a neutral grey. I figure starting with something neutral will help me ease into “relaxed weekend” look and assure that I’m still on trend.

 

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I’ll admit when it comes to fly casual looks I’m lost.  My current plan is to ease in by pairing these neutral kicks with jeans and graphic tees before I work my way into more complex pairings and eventually – GASP! – another pair of sneakers!

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Shirt ~ Express (try this) | Pants ~ Express (I’d try these)| Shoes ~ Jordan | Jacket ~ H&M

Esta Fiesta is a Brooklyn based blogger with a love of music and finding new shoes. When she's not watching a movie or testing out new hair products she can be found doing Pilates - but only so she can eat from the waffle truck of course! Follow her Tweets at @ItsEstaFiesta