Day 1: In front of the LOFT store below the AOL offices, posing with a new friend. Photo: Damon Dahlen

If there's one thing you should know about me, it's that stripes are my weakness. There's something inherently classic and European about them -- perhaps Coco Chanel, Jean Seberg in "Breathless" and Gondoliers are to blame.

I did not believe in love at first sight until I saw this knitted boat neck sweater in the window at LOFT. I often wear the topper with cropped black pants and flats, but one day I was inspired to don the piece with a Talbot's sequined pencil skirt, edgy lace-up booties and feather-detailed felt hat. (Image at left)

A colleague noticed my new approach and proposed a five-day style challenge: wear the same sweater five different ways for the week. We've all seen it, we've all tried it, and somehow fashion magazines do it flawlessly every season: the one-garment-multiple-ways editorial.

So with no stylist in sight and Day One under my belt, I started to plan my week's ensembles. I even set my alarm clock for 15 minutes later, figuring my morning routine would be much shorter without the pressure of choosing a top. Boy was I wrong!

Day 2: All I'm missing is a guitar. Photo: Damon Dahlen

Day 2: For whatever reason, Pat Benatar was able to make preppy staples like striped tee-shirts and tweed jackets look tough. Paired with tight, black pants and edgy makeup Benatar was the ultimate "Heartbreaker." For Day Two of my style challenge I took a walk on the wild side with a studded blazer, equestrian leggings and leather Calvin Klein boots with chain details (They've been re-soled three times - talk about tough love!) To make sure my look was CBGB-approved, I added two studded, double-knuckle rings from Aldo and my recent lip color of choice: "Vesuvio," by Nars.

Day 3: Today's motto: be creative! Photo: Damon Dahlen

Day 3: With warmer weather approaching, I need to transition my winter wardrobe into spring. Layering -- an art form which I have yet to perfect -- is a sure-fire way to prepare for any weather Mother Nature may bring. I combed through the personal style diaries of our Blogger Network seeking boho inspiration for Day 3.

A lot of the girls have a more-is-more approach to dressing, so I got creative with proportions: I started with my "mullet-dress," a Suzanne Rae creation that is short in the front and long in the back. I layered my LOFT sweater over the dress and added a chunky Navajo-inspired wrap cardigan by Ralph Lauren. Those Frye boots are about eight years old, I used to wear them horseback riding! And like a true gypsy I put on as many rings as my fingers could handle: a large ornate number from blueberi in Brooklyn, a gifted pyrite ring, light blue enamel ring by La Petite Princesse and a Stanton-James wire "LOVE" ring. I opted for Earthy necklaces: a stone pendant number I made and a freewater pearl necklace given to me by my grandmother.

Day 4: Throw back. Photo: Damon Dahlen

Day 4: Like any high schooler, I went through many phases -- the most prominent being my preppy days. Even though I hadn't hit a forehand in a few years, I wore tennis skirts to class. I paired madras pants with collared shirts (collar almost always popped) and pearls were always worn. Always.

On Day 4 I took a little inspiration from my yearbook and styled a look that would be considered country club chic. I wore a Banana Republic chambray shirt under the LOFT sweater. And, no -- I did not pop the collar. I did, however, add a pearl necklace (gifted to me by my grandmother) and bracelet (J.Crew.) My cropped trousers from the Gap were paired with lace-up wedges (also Gap) and J.Crew wool blazer hung from my shoulders. Menswear accessories like a Timex watch and my father's old leather belt made the look a little "Annie Hall," one of my style icons.

The final touch was a bright ribbon tied at the top of my pony tail: on game days the field hockey team would wear our kilts to class and tie bows in our hair.

Day 5: My mother's daughter. Photo: Hannah St. Lifer

Day 5: I inherited my mother's love for fashion and deep appreciation for style. So you can only imagine the joy she found in styling me for my fifth and final outfit. After a handful of odd jobs, my mother opened her boutique Sadie in my hometown where she sells dresses, skirts and amazing vintage-inspired jewels. The final product was a bit Audrey Hepburn and a dash "Mad Men." The circle skirt comes from an amazing designer who owns a thrift shop in SoHo called Legacy, and the flats are Jack Rogers with wonderful stitching details.

My favorite part of the outfit has to be the Lulu Frost porcupine quill earrings from Lisa Salzer's Modern Pioneer collection. The edgy jewelry elevates the outfit from ho-hum to hardcore.

So without a stylist and plenty of inspiration, how do you think I did? Leave your thoughts in the comments section below and make sure to let me know the one piece of clothing you wear over and over again.