Why I Love #OOTD

04/14/2014 11:25 am ET Updated Dec 06, 2017

I went to a private school where I wore a sailor-esque uniform for 15 years. No surprise -- I loved casual Friday's.

I remember wearing my wedding dress anyways and feeling empowered by the reaction I got.

I got cast as a Brooklyn hipster, Chinese delegate and upscale barhopper -- all in one season of "House of Cards."

I love looking at characters and their wardrobes on television because they're supposed to reflect the real world, stereotypically. Dressing up or down is like acting or putting on a show in real life. Fabric and the way it's stitched together tells a story and in the end, you embody the person you project. The point is -- clothes make part of who we are, want to become or seem to be. Human instinct allows for instant judgment and inferences based on material pieces and the way they and you are put together, effortlessly or not. After all, we are naturally visual people.

So if we own our clothes, why don't we more often own our looks?

Clothes are a form of expression and we could gain something by being less risk-averse. Finding your personal style is a matter of taking some risks and seeing what sticks outside your comfort zone.

On job interviews, at home or at work, we tend to be more conservative and try to fit in with the office culture. At times, you want to blend in with your peers. I recently spent a good fifteen minutes deciding between Chanel smoking slippers and ankle boots (flats won) because I was excited/anxious about eating at the Conde Nast cafeteria. I dreamt about meeting Anna Wintour. I didn't, but I remember what I wore, just in case. For me, I thought, it was about making my own mark in the environment of possibilities.

A few days later, I attended a mixer at an art gallery. I didn't know anyone, and I wore a Russian bomber hat. I decided to be inspired by the setting. No one else had anything on their heads. I stuck out like a thimble on a thumb. Men wanted to feel the fuzziness. One girl who said she could never pull it off. Not true. I am simply emboldened by my fashion choices.

(Photo courtesy: IvyConnect)

That's where "outfit of the day" comes in. There are more than 26 million posts tagged #ootd on Instagram. Whoever started it, was onto something.

Knowing how to work it on your own terms will help you work a room, if you want. Clothes can give you confidence to start conversations or cloak you with insecurities to transform you a backdrop. I mean, think about it -- you'd be naked otherwise so why don't we bare different sides of ourselves when we get a chance? Dress without fear and you'll leave the door, without self-judgment.

Here are some additional tips:

  • Be comfortably confident and vice versa.

  • Experiment -- just once, just a little and see what happens. Remember, you can always take the edge off. Maybe start with accessories.
  • When shopping, there's no shame in going straight to the sales rack or ask for a discount, like no sales tax.
  • Try to stay away from trends and invest in good clothes. Fashion is cyclical but if something speaks to you or is evocative of a positive feeling, get it. Osh kosh b'gosh, I wish I had kept my overalls from middle school.