Like Kim K. But with less butt.

I’ve become 1 of those women. Evidently, I now have a stylist.

My Guy and I attended a gala benefiting the local children’s hospital. It was a party! For the children! In a moment of generosity, I bid on 2 hours with a personal stylist. You know, to get the bidding started.

You know that chardonnay they serve at banquets? The free wine that after the first sip you think, “Oh, that’s not good?” But after the third glass, you think, “Damn, that’s a mighty fine wine?” Well, that same beverage helped me keep bidding on the services of the stylist even as the bids went up. After all, it was for the children!

So, I ended up winning 2 hours with a personal stylist. She can help me go through my closet or take me shopping.

“OMG. Your hangers don’t even match?”

Except now I’m somewhat paralyzed. What do I say to a stylist? Here are some options:

  • “I would describe my personal style as ‘OK?'”
  • “I work from home and don’t want to look like a frazzled mom because I don’t even have kids and actually have time to spend on my appearance even though I obviously don’t?”
  • “I wear jeans and t-shirts and Banana Republic stopped making my go-to t-shirt so can you please just recommend a new t-shirt brand? Thanks.”
  • “I used to be skinny and somewhat fashionable but now I’m 40 and I don’t care. Well, I care, but I don’t care? I just don’t want to look Amish? Does my hair make me look Amish?”
  • “I look dorky but I’m actually really cool. Like, mega-cool. Just take my word for it. Please?”
  • “I recently hurt my foot so all I can currently wear are sneakers, but that doesn’t mean I’m Generation: Easy Spirit. See also: I’m mega-cool. Just take my word for it?”
  • “Please don’t make me shop at Forever 21.”

I’m torn between 2 options. The first is that the stylist and I will become fast friends, and she’ll introduce me to all her stylish friends as “My FAB friend Becky – you know, the one with all the great accessories who’s always so pulled together and such an inspiration to me both creatively and as a human being?” The second option is that the stylist will berate me for being so completely unfashionable and will then describe me to all her stylist friends as “That HORRIBLE woman with the jeans that were hand-me-downs in 2004 and who must appear homeless 97 percent of the time and who basically looks Amish except less stylish?”

These seem like the only 2 options.

The truth of it is that we all want to look our best. And we all need a fresh set of eyes every once in a while. But also … I feel like I’m dressing for a part that I haven’t yet defined.

I’m not a mom. I’m not a corporate denizen. I’m a writer, but not a sweaty, hardboiled journalist or a flowery romance novelist. I’m 40. I’m 40 and I’m still trying to figure out what I want to be when I grow up.

There. I said it.

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  • Reply Becky February 25, 2016 at 12:58 pm

    I'm 46 and still not sure what I want to be when I grow up. And my go-to tee shirt is from Old Navy, only they stopped making that style at least 5 years ago, probably longer, so that my black tees are more like grey. My 14 year old daughter, who fancies herself my personal stylist, is rather disgusted with me and wonders pretty much daily why I insist on looking homeless all the time. I'm pretty sure anyone you pay to be a stylist will be much nicer about telling you you look homeless with far less eye rolls.

  • Reply Jen Anderson February 25, 2016 at 1:43 pm

    OK, so I wrote a blog post for a client about personal stylists for real people, so I'm kinda jealous that you're getting to do this. What's actually going to happen is that they'll go through your closet with you, show you ways to combine things you already have, teach you how to dress for your body shape and identify which pieces you should add. They should be able to tell you where you can get t-shirts from. They will have zero celebrity clients to compare you to. Their usual clients will be executives who need to learn to dress like the boss to get ahead, and people leaving corporate jobs who have a closet full of suits they don't need anymore.

    You may find it so helpful that you schedule time with your stylist a couple of times a year to update your wardrobe. Enjoy!

  • Reply Kari Wagner February 25, 2016 at 1:52 pm

    Tell her you like black and gray.
    Funeral chic as I like to call it.
    Oh sorry, that is me.
    Good luck and God speed.

  • Reply Cha Cha February 25, 2016 at 2:57 pm

    Becky, I think you look pretty. Also? 14-year-old girls are terrifying. And if I find a good replacement t-shirt, I'll let you know.

  • Reply Cha Cha February 25, 2016 at 2:58 pm

    Jen, thank you! This makes me feel less psychotic. I will report back!

  • Reply Cha Cha February 25, 2016 at 3:00 pm

    Funeral chic? Hahaha! Don't worry – I have two black dogs. A nude and white wardrobe would only highlight the dog hair and make it more obvious that I'm a crazy dog lady.

  • Reply Green Girl in Wisconsin February 25, 2016 at 10:31 pm

    You are FABULOUS. There. I said it. Typed it. Whatever. And you wore such cute rockin' scarves and cardigans and looked totes adorbs at Erma Bombeck, so you had to have been drunk to buy the stylist.
    That said (typed?), I can't wait to hear how it goes!

  • Reply Karen (formerly kcinnova) March 1, 2016 at 6:09 am

    It's always dangerous to bid on things while lubricated, but that's the only way my husband gets through those things, which is how I came to have 3 hours of a home decorator's time about 8 years ago. Our furniture doesn't match and we have no style, so I was a little concerned but the entire experience was awesome! She helped me choose new paint colors for the kitchen and dining room, observed our tastes and need for lighting and seating in the family room and brought in a few lamps and an ottoman. She rearranged the furniture and wouldn't let me see it until she was done. It looked great and we kept it that way until we moved.

    With the comfort and truth-telling of your friends who've posted above, I know it will be awesome when you tell us the rest of the story.

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