09/06/2012 11:35 am ET Updated Nov 06, 2012

Angelina Jolie's Stylist Dressed Me For A Night Out (PHOTOS)

If left to my own devices, I would wear the same strapless printed maxi dress, long gold pendant necklace, flat woven sandals and leather cross-body bag every single time I go out. My typical outfit is perfect for brunch with friends or a day at the beach -- but for bar-hopping in New York City? Not so much. Although I love my low-key, 70s-inspired California style, I'll be the first to admit that dressing evening-appropriate is not a skill I possess. My look is anything but glam, which is what comes to mind when I think of going-out attire: shiny, sparkly, tight-fitting, uncomfortable -- and SO not me.

Before you dismiss me as a fashion dud, I swear I'm not totally clueless when it comes to style. I'm constantly reading and writing about fashion, and I'd like to think that I have a good aesthetic sense. But we all have our sartorial challenges, and mine has has been to find a going-out look that still fits my laid-back, earthy style.

So, after the third Saturday night in a row that I reached for the aforementioned printed maxi, I realized that it was time to amp up my going-out look. I enlisted the help of celebrity stylist and T.J.Maxx spokesperson Jen Rade, who's worked with the likes of Angelina Jolie and Katherine McPhee, to teach me how to dress up -- and how to do it my way.

Fortunately, the super-stylist came to my rescue and showed me how to create a great going-out look for fall. She picked a sage green BCBG dress that I initially pegged as being too office-friendly for evening. But adding a pair of suede lace-up Juicy Couture booties, wide leather belt, chunky gold jewelry and colorblock leather envelope clutch completely transformed the look. It was glamorous in sexy in a Bianca Jagger kind of way -- it was earthy and '70s-inspired, yet totally worthy of a rooftop party or night on the town. We topped off the outfit with a brown striped Cynthia Rowley cape. As a bonus, Jen showed me how to use the cape, paired with a rust-colored Vince tee, black Rag & Bone jeans and booties, as the focal piece for a comfortable but sexy daytime look.

Click through the gallery below to see my transformation, but don't expect any Angelegging from me any time soon.

Angelina Jolie's Stylist Dressed Me