So, by now everyone has seen the new Barbies. They’ve released a curvy Barbie, a tall Barbie, a petite Barbie and a a few others that I will look up later. The point is that Barbie is trying to be a little bit more realistic with the body measurements of real women. It seems as good a time as any to talk about Barbie’ wardrobe and what she chooses to wear to work.

Women have a lot more freedom and creativity in their style than men do when it comes to workplace clothes. In the tech-bro friendly Bay Area, women can literally get away with wearing anything at all.

When I was asked to mentor someone at our big company a few years ago, let’s call her Barbie, there was a wardrobe and body issue that was at hand. Me, as mentor, friendly colleague who cares about you, had to deal with. Boobage. Barbie doesn’t really have this problem because her boobs don’t move but my friend Barbie had been wearing a very loose and old bra that didn’t do it’s job of holding the girls together and in. This friend of mine was dressing rather sloppily, like she was still in college…wearing t-shirts that would reveal her entire shoulder and the thin, aging and frail little bra strap beneath it.

To make matters more delicate, I had at least 2 other folks that worked with this person who I was mentoring that came to me about the bra and boobage issue, wondering what should be done. Someone needed to tell her that her boobs were making other people uncomfortable. They were so loose and uncontrolled! She seems to sling them all over the table and around so casually!

I was really at a loss for what to do. I am not a mother and if I did have daughters I vow to tell them to use their boobage strategically, they can get you a lot of what you want, if used correctly. But this Barbie I am supposed to be mentoring, she is my age, she must know what she is doing with her boobs, who am I to tell her to strap them in!?

I decided since others approached me about it the least I could do was share the info. We went for a walk over to the Ferry Building, strolling through like girlfriends. I sprung it on her with a I have something to tell you that is very hard to say: You need a new bra. Several people have mentioned to me that you don’t seem like you’re dressed for the workplace. I’m sorry I felt like I had to pass that on. Then I handed her a gift card to Victoria’s Secret. She was embarrassed but didn’t miss a beat and she thanked me.

To this day, I still feel like a heel having told her how to dress. It didn’t make a difference in her career at the company we were at together. If anything, it put a wedge between us – Me as the follower of the rules, her as the rule breaker. I did my best. (did she use the gift card and could you notice the difference?)

So when Barbie comes on the market with new styles of her body, I worry if the clothes will fit. Barbie doesn’t really wear a bra and so we can only draw these imaginary parallels anyway but really, what would Barbie do?