We catch up with creative connoisseur Bryn Newman of in today's Style File.

You're on a first date, what shoe do you wear? Chunky Heel Black booties. No embarrassing trips please.

What's one fashion rule you always break? Wear the opposite of what everyone else is wearing.

When it comes to shoes, how much is too much to pay? The most I have spent is $250 on a pair of shoes on sale from $625

Who is your favorite shoe designer? Freda Salvador. Always.

If you were a shoe, what shoe would you be? Clogs because I am truly a hippie deep down.