I hosted a brunch this afternoon for my parent’s 60th birthday. A beautiful summer day in Laguna Beach, CA and sipping mimosa’s with middle-aged entrepreneurs and retired physicians seemed like the perfect occasion for me to wear my new beige linen blazer that my tailor made last week. The blazer has a two-button front, side vents, a notched lapel, flap pockets, tan contrasting handpicked stitching around the lapel and buttonholes, and fully-lined in a cream colored silk. I wore it with a burgundy polo and dark blue jeans.

To be quite honest, I wasn’t prepared for the amount of interest and admiration I received from family and friends over the quality of the cut and fit of my blazer. What followed was an onslaught of curious questions about DressMonkey and its business model: Are all of your products made in China? How long until I receive my order? Where do you buy your fabric? You’re saying I can login to your website and customize my clothing and see preferences in real time? Who is designing your website? Are you having trouble finding quota for your dress shirts? When can I start buying your clothes? The questions kept coming and coming, and after what I had felt had been an entire afternoon of sales pitches and interrogation, I was finally asked the question that matters most in any purchase, even to the older, baby boomer demographic:

“How much would a jacket like this cost me?”
“Less than $100…” I said.

I had a pen and paper pasted around the party.

Five minutes later, I had the names, emails and measurements of the first eight DressMonkey customers.