Over-Sized Flare Jeans: Road Test (PHOTOS)

10/19/2011 11:42 am ET | Updated Oct 11, 2012

Let me tell you a secret: I have three pairs of the same pants. They're black, cropped trousers from the Gap. Heck, while I'm airing my dirty laundry - one pair is a size larger than the other two, reserved for those days I feel bloated.

These black pants have become a part of my uniform - comfortable and loyal wardrobe staples.

But each time I browse the racks of Barneys NY or scroll through Net-a-Porter for fall purchases, my gaze wanders towards the high-waisted denim with exaggerated flares, a foreign and mysterious garment I fantasize about wearing, but never act upon.

I have tried many outrageous trends - rose gold hair, turbans and nude underwear, to name a few - but nothing prepared me for the morning I dared to wear flared denim.

I'll save you the details - but as I left for work (a full half an hour late, mind you) the contents of my closet laid in piles on my floor. Before, when I put on my black Gap pants I had an entire stock of ensembles to choose from, but standing there in my new J Brand Jeans, I suddenly felt as though I had nothing to wear.

Even in NYC, people took notice - my bus stop BFF told me I looked nice (typically, we just nod at one another) and coworkers applauded my styling. (I looked up photos of Rachel Zoe for inspiration, natch!) I even spoke to Wayne Shulick, President of Denim Habit, and he revealed (after taking notice of my flares) that, "wide-legs are definitely coming back," listing J Brand, Hudson and Rag & Bone as brands that are getting it right.

While I loved the overall slimming effect of the flared jeans, every time I looked down I felt like a clydesdale horse. And with Halloween around the corner, I feared others would mistake me for wearing a '70s-era costume. The trick with this trend is to know how to wear it - sure it looked amazing on the models at Chloe, Derek Lam and Pucci, but I am a size 6 and hippy. These J Brand Jeans are perfect for those days when I want to show off my curves - I'm always proud to have them - but sometimes I just want to keep it simple in my black slacks.

Meanwhile, check out trendsetters who have rocked the look.

All photos by Bobby Doherty

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