Amy Fairchild is a singer-songwriter and real estate maven who lives, works and plays in and around the Boston area. When I met her many moons ago (late 1990s), Amy was winning awards, turning down record deals, playing gigs at CBGB, Bitter End, Rockwood, and many other NYC venues, as well as across the country and on the gold coast. Over the years, she has shared a stage with Sheryl Crow, Sarah McLachlan, The Bacon Brothers and other rockers. As a cross-genre singer-songwriter, Amy gets buzz in rock, folk and pop worlds, which hints at the depth and diversity of her writing style.

Amy continues to write, sing and play guitar (and piano when I beg), while balancing her creative talents with work in real estate. When I was packing for a recent trip with Amy to Old San Juan and neatly folding my Denim Iconic Jeans, a gift from Yael, I thought, “She would LOVE these, especially in a fancier fabric she can wear to work—then, with a quick change of heels, hop on stage in ridiculously comfy yet totally chic jeans that shimmer in the lights.” I know, welcome to my brain.

Success! She loves them and, as suspected, they fit her like a dream. Amy’s wearing our FLORAL ICONIC STRETCH JEANS that are available in Black (here) and Chocolate, both beautiful.

We went out in Old San Juan to visit El Convento, a luxury hotel that was built as a convent hundreds of years ago, and took some photos of each other in our Iconic Jeans. The backdrop was so dramatic in this landmark hotel. And I love how her crop top looks and shows off the sleek flat front of these mid-rise stretch jeans.

Now that Amy is an Alembika Jeans devotee, we asked her our fab five #AlembikaWomen questions.

What do you do for work?

I’ve been a performing and recording singer-songwriter for 30+ years. At one point I did work as a musician exclusively, but now I also work in real estate in the Boston area. I answered an ad after moving to Boston from NYC in 2002 for what I thought would be part-time work while I continued to build my music career, and found that I quite enjoyed it as a full-on, second career!

What do you do when you don’t know what to do?

Go for a long walk in nature. Clean the house.

What would you do if you had the whole day to yourself?

Well, I actually DO have the whole day or part of the day to myself fairly often, as both of my career paths are self-motivated, self-employment situations. At times, I find myself free of both jobs for the day or a few days. I play guitar and write songs or sort my sock drawer and closet… again. I also love thrift stores, second-hand furniture and vintage/consignment stores. I seek them out wherever I go when I travel and at home.

Note: It’s true. Amy scoped out a bar Anthony Bourdain had visited, off the beaten path, and around the corner from a well-curated vintage store (not a coincidence) that we both walked away from with fabulous “scores.”

What is the best thing about being a woman?

I used to really like being a woman… Not that I don’t now but, when I was younger, I think I sometimes used it as a defense weapon, perhaps self-defined mostly by my outer, womanly surface-y self to gain attention. I don’t do that much anymore because with age comes more confidence from within. But it’s nice to know that I still could.

What is the one piece of clothing you cannot live without?

Black, stretchy cotton pants that can double as “around the house” or “out and about.” And recently, a cashmere shawl that doubles as a poncho, throw and scarf—and Black Iconic Jeans.

To hear Amy’s music, you can visit her website. If you’re in the Boston area, stay posted about shows @therealamyfairchild on Instagram.