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'That Nail Polish Looks Terrible:' Words Of Advice From My Jewish & Stylish Grandmother

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My relationship with fashion started really early on. The first lunch outing I ever went on was spent in a baby carrier atop the table of the cafe inside Saks Fifth Avenue. When it came to reading, the first word I recognized well enough to speak out loud was "Macy's."

The reason for this early intimacy with shopping? My super fashionable grandmother, or Nana as she requested to be called upon my birth ("grandmothers are OLD," she argued.) At 82-years-old (and still working full time!), my Nana continues to be the most stylish person I know... and I work in fashion.

Now, before we begin, let me be clear about something. I LOVE my Nana. She is caring, thoughtful and a fiercely strong woman who has served as a role model my entire life. Having said that, there are still a few things we disagree on. Things like whether writing is a "real job" or my extreme "interest in the Internet." What we do have in common, is our passion for good style. Shopping and sharing* clothing has been the glue that turned two people who can't see eye-to-eye on a whole lot into, well, best friends.

But, like any best friends, sometimes we disagree on what looks good and what doesn't, too. In honor of Mother's Day this weekend, I've decided to share a few of the most memorable fashion moments we've sparred over through the years.

You must always have a manicure... and color matters.

Once I showed up to Nana's apartment in what I thought was a great outfit, cute accessories and mint green nail polish. She opened the door, gave me a once over and said, "what kind of color is that on your nails? I hate it."

Your shoes should match your bag

This one I can actually get on board with. The first time Nana pointed out that I was wearing a blue bag and brown shoes, I laughed in her face. Now I can't leave my house without double checking that they go together.

Messy hair is not as cute as you think it is.

Sometimes I don't feel like showering. By sometimes I mean pretty much any Saturday morning. Conveniently, Saturdays are usually the days Nana and I get together. The last time I rolled out of bed, threw a trusty hat over a messy braid and showed up at her house, she said: "Is that in now? Not brushing you hair?"

Never wear heels -- if you're under 25.

Until I was about 24 (I'm 25 now), Nana yelled at me every time she saw me in a pair of heels. I'm not sure if she's just given up hope on me, but she hasn't said a thing since my birthday.

Earrings are a must.

It used to make her CRAZY that I never wore earrings. I don't know why I didn't wear them, after all, I DID have holes in my ears. I just didn't feel like wearing them. She got so fed up that after 22 years she gave me HER nicest pair just so I would wear them. Now that's dedication.

...Just nowhere besides your ears.

More specifically, no where except your earlobes. I used to have a nose ring that I'm pretty sure crushed her soul a little more every time she looked at it. Now I've ditched the nose ring but have a tragus piercing, and I can see her biting her tongue every time I tuck my hair behind my ears. Hey, at least I'm wearing earrings, right?

It's not just hair, and it doesn't just grow back.

I recently chopped all my hair off. Nana hasn't seen it yet, and the next time I'm seeing her is Mother's Day. The last time I cut all my hair off she had a panic attack right there in the salon. Happy holidays, Nana!

Of course, she's also imparted a whole bunch of wisdom on me over the years, like:

Cherish your brows.

Back in the day when Nana lived in Israel, she had her eyebrows threaded and they never grew back. So I don't do much else besides tweeze anymore.

Put a belt on it.

This one is pretty self explanatory. When in doubt, add a belt. It turns an outfit into a look.

Anything can look expensive... if you wear it the right way.

Nana wears something she bought for $10 and gets more compliments than I ever do on the things I wear. It's about the confidence, she says.

Being a total badass probably helps, too.

To see more photos of my Nana, who doesn't know quite how famous on Instagram she truly is, click here. Happy Mother's Day to you and all the awesome, stylish moms in your life.

*By sharing I mean I wear all of her clothes that she "doesn't want anymore." Seriously.