Interview Attire Dilemmas (Again)

A long time ago I blogged about what to wear since I was interviewing for non-corporate roles or companies. As of late, I’ve been headhunted a lot and am running across the same dilemma. All my interviews are at companies that either never existed until recently, aren’t traditional companies, or are cutting-edge leaders that are forging new paths they don’t “obey the rules,” and thus, corporate culture is highly specific to that industry. What throws me off more is when I interview for senior management at a very atypical company. Do I dress as the “gets stuff done” EA or cater to the company ideal of “we’re different because we start trends, we don’t follow them”? Decisions, decisions, decisions!

As you may know, my standard interview outfit for being a CEO’s assistant is an all black suit with pointy heels in black. Since all of my jobs have been pretty corporate and I dress fairly conservative at work anyway, this has worked well for me - until a few things made me start to think...

Because I’ve been meeting with all these companies, I started to notice differences I never had exposure to, coming from mostly a corporate, Fortune 500, all business all the time background. The companies I met with were legitimate, successful, and reputable, but they became that way for not following whatever was mainstream. And how they differed was evident from the first point of contact. The communication was breezy, very casual, peppered with slang, as if we had known each other for years. The meetings were in coffee houses or over meals. They didn’t want to see my resume. They just wanted to sit and chat. Through the grapevine I heard I was complimented for being cute because of my large dimples. I was advised not to wear the suit. It was also suggested to not have my hair up in a clip. I was advised to wear something very trendy and specifically a dress. Because fitting in with a company’s corporate culture is imperative, that also comes across in the way one dresses.

I had difficulty coming across young, hip, and trendy, without it becoming too cute, too green, and not business enough. And how does one wear a dress to an interview without it becoming too feminine and alluring? I finally settled on a speckled black, grey, and white long turtleneck sweater dress that came down to mid-calf, with long sleeves, a wide silver and black belt to give the dress an empire waist, and low red heels. I also wore an oversized ring on each hand to accessorize a bit.

When one is only 5ft tall and petite, it’s sometimes hard to be taken seriously. I’ve had colleagues see me out in LA and not recognize me at all in casual clothes, or mistake me for a junior high kid in jeans and a shirt. In the past, I would have rather erred on the side of being taken too seriously in a corporate suit rather than too lax in something a bit more casual. However, knowing that most people would rather work for someone they like that they have things in common with that is a pretty good employee versus someone stellar and they like less, I should probably tone down the corporate attire and let my resume (hopefully) speak for itself...

Have you had similar dilemmas? And what are your suggestions for dressing for various types of companies - technology, advertising, architecture, music, and other industries that are not typcial business, law, real estate, or finance companies? And do you wear different types of outfits for the head of HR, the assistant, and the CEO or other executives that you interview with? What have you found that works or doesn’t work?