How many cocktail dresses does one "need"?


Dec 13, 2009
Thank you so much for all the advice, I really appreciate it. It's given me a bit to think about. I will look for 2-3 more dresses and go from there. DH has agreed to go to the opera with me, so I will do a small subscription, committing to three operas this fall.

I inherited some jewelry that is in old fashioned settings that I haven't been sure what to do with. Converting one of the diamonds to a pendant sounds like a great idea. I may have enough stones to make some drop earrings as well, or I can get a new pair if needed.

I work in a creative field and own my own (very small) company, so I have a lot of leeway in how I dress. DH is C-level at a much larger company that is not "arty" like mine but also nowhere near as conservative as law or finance. The core group that we see are fellow execs and one investor from his company and their spouses. While I am at "the top" of my company, I want to maximize networking opportunities and impress potential clients. It's also possible I will want to seek outside investment at some point.

I'm on the fence about black vs not black. The president's wife wears black exclusively, so it seems ok.


Apr 26, 2016
Ontario, Canada
A lot of the suggestions on here have been great. If I were in your position, I think the colours would boil down to what I actually have and can find in the stores online or off in my city, and what actually looks good on my body. Personally, I strive to buy colours and patterns, but sometimes black just looks better on my body. If my budget were low, I might consider asking people I know who trust me to borrow some jewelry or dress for the evening.

I'd say, given that you have two black dresses, it might be worthwhile to try to find more dresses that are not black or not all black. But definitely, only buy what looks good on your body and what fits with your taste.

Finally, I want to encourage you to think of this as an important opportunity to shape your image as someone who owns her own company. For these six events, think of yourself as crafting an image, as if you are like Anna Wintour. Dress in accordance to the principles that you think define your company/worldview/image. For example, my husband is a professor. For his first university interview, he wore a traditional suit and dress shoes. He got the job. When he went to his second job interview (three years later), the stakes were lower, even though the new university had a better reputation, better dept, etc. He decided to be himself (his research is in video games), and wore a button down, tie, blazer, cargo pants, and sneakers. For him, what was important was defining his image to his colleagues, and about showing that, not only is he professional, but he was up and coming, and his research was new, fresh, and engages young students in ways that the department at present didn't. He got the job. Since then, he dresses like himself for job interviews and work events.

I know women at work who only wear black and that is part of their image that they want to craft. Some aiming for a beatnik type charm. Some aiming for a gothic/dark aesthetic. What I am saying here is that I would try to think of the dress you wear as deliberate and as an opportunity to create an image you want projected and associated with your company.