When I first started selling wine, I was coming off of a stint at a very high-end, New York-based steakhouse. We wore suits every day- dark suits, white shirt, dark tie. Nothing too crazy or fancy. We were to look like we worked at an old-school, expensive, lots of dark wood and leather steakhouse (which we did). When I got my first wine job, the expectation was similar- it was owned by two older brothers that both wanted us in suits. However, this presented a small problem. You see, the Boston metroplex is essentially cut in half by the Charles River. On the south side of the river is Downtown, and most of the fancy joints. The sales people here wore suits and shiny shoes everyday. On the north side of the river was Cambridge and Somerville, where I worked. Now I can see how one might think "Oh, Cambridge- where Harvard, MIT, Tufts, etc. are- you should probably wear a suit there, too". Nope. This was a land where people dressed down to look smart. If I wore a suit everyday, I would probably be the only person in any room that I went into dressed like that. I very quickly, and in a clandestine manner, started wearing button up dress shirts and slacks. I learned that when a guy my size walks into a restaurant or retail shop in a suit, often times the owner doesn't trust me. They see me as a suit, not as someone that wants to help them make money. I literally had accounts ask me to take off my tie, so they could talk to me. The clandestine part came when I would keep a neutral-colored tie in my car, because my boss didn't seem to share my sentiment and he had a habit of surprising me by joining me in the middle of the day. In fact, he was pretty brutal the times he caught me without a tie. He also didn't have any friends.
Then a fresh, cool breeze started blowing in from California. This breeze came in the form of the "Tommy Bahama" style silk shirts that wine guys were suddenly wearing. This was a great thing, especially when I moved to St Louis, where the summers are ridiculous.
I have noticed around town what most of the wine guys wear. In the summer, a lot of them are in dress slacks and golf shirts, or silk shirts I just mentioned. I also know of a company that requires their men to wear a long sleeve shirt and tie, even in the summer. That's just mean.
For the new company, we have adopted a strategy of dressing as-good-as, or better than, anyone we meet with in that particular work day. Most days thats exactly what I described- Polo Shirt, Dress Slacks, dress shoes. I might don a nice pair of jeans on Fridays when I'm out running around. If I'm visiting a hotel, or a really nice restaurant, I'll put on a sport coat. I want to work as much as I can without ever wearing a tie.
Thank God a lot of my accounts wear jeans and t-shirts!
Okay, so that has nothing to do with "sippin". For those of you who want a wine-tip, get some Zestos Malvar- it's crisp, delicious, and sold by the glass at Farmhaus.