Bonus Content: A Sunday Roast

From the person who knows me and how I shop best.

Last night, I had dinner with My Best Friend #Jess at Hart’s in Brooklyn, where we caught up over lamb burgers with anchovies. I told her about the launch of this newsletter, and how I kind of came out guns blazing. While I don’t have any regrets, hitting ‘send’ did set off something of an existential crisis for me. Who do I think I am?? Also, who do you think I am? I realized that what needed to happen next was a good old fashioned roast. And who better to take me down a notch than the person who knows me and how I shop best?

Jess and I lived together on-and-off for about seven years—first as roommates in college, and then as roommates in Brooklyn. She knows the contents of my closet better than I know the contents of my closet, and was there for every outfit change, every online purchase, and every return to the post office for the majority of my twenties. She was also, whether she liked it or not, the recipient of my unfiltered fashion criticism, day in and day out. The fact that she put up with me for so long—and still puts up with me—is truly a miracle, and one of the biggest blessings of my life. So when I asked her if she would roast me for this newsletter, it was a no-brainer. She’s been waiting for this moment since the day we met.

Emilia: Would you describe me as a critical person?

Jess: [Laughs.] I feel like that's like defining the word with the word.

I would say yes, definitely. As your roommate, it ran the gamut from a slight aversion of your eyes to: “….You look cute?” That was the most I got. But the real problem was when you would look at me, and there would be a prolonged silence, and then you would say nothing at all. That’s when I knew I needed to change immediately.

The silently critical up-down is, unfortunately, a terrible habit I picked up in the Condé Nast elevator.

The Condé Nast elevator is one thing, but imagine that in the safety of your own home!

Awful. I’m so sorry. But just to put my bad behavior into context… I don’t think I was doing this on like, a random Tuesday. It was more when we were getting ready to go somewhere and the outfit was a question-mark, perhaps?

Yes, it was even worse. It was when you knew that I was at my most vulnerable trying to look good!!! You would be your most, most ruthless.

Damn. Okay, I take responsibility for that. But also… Sometimes you asked!!!

Sometimes. But only sometimes.

Would you call my criticism judgmental or constructive?

I would say you find the gray area. If probed, you will always be constructive. And your suggestion would always improve the outfit. But God forbid I actually just liked my outfit, it was more the former.

[Sigh.] And what is it like shopping with me?

I would say the longest running theme is, “you don't need that,” which is true 99-percent of the time. But also, that’s not really why we go shopping, you know? The worst is when I venture to take a risk and pick something out for you. That’s usually met with a ‘no,’ and an accompanying facial expression.

Would you rather just shop alone?

I like shopping with you because I’m kind of an impulsive shopper and you are a good voice of reason. Except when it comes to your own shopping, when you employ my most favorite and oft-quoted justification for buying really expensive things, which is: “I will pass it down to my grandchildren.”

They are so lucky.

Sure, somebody's grandchild is getting your stuff when they buy it two months later from you on Depop. Or maybe an actual grandma is buying it from you when you list it on The RealReal. That’s a way more likely outcome than anything sticking around in your closet long enough for your actual grandchildren to receive it.

Since we don’t live together anymore, we now just text each other links back and forth all day long. Am I still just as critical?

You often say things like: “You can do better.”

That’s me trying to be constructive!

Well, I think you have a seriousness to your style. Even when things are playful, which they often are, they're like, seriously playful, or Prada playful, you know?

Go on…

You have a good editorial eye, in that sense. But I think I tend to be a little bit more eclectic in what I wear, and sometimes go for something a little bit more messy or funky. And I feel like that is sometimes not really seen by you.

You’re right, that is a blind spot of mine.

So when you say, “you can do better,” I feel like you actually mean: “you could buy the more classic-slash-serious-slash-expensive version of this, and it would be better.”

Mmm. I can’t argue with that.

Sometimes, I'm a little more, you know, gay.

I also can’t argue with that.

Oh gosh, I remember this one night for so many reasons: we were going to a house party, and you made me change, I think, like, four times.

Okay, I didn’t make—

And the outfit was perfect, I admit. But then we ended up at Nowadays with the youth, and I had a run-in with a really hot Gen-Z person in the bathroom. They were wearing like, a ripped napkin as a shirt. I don't know what Gen-Z wears, but it was very ‘90s, or whatever. And I'm there in my silk button-up, buttoned all the way up, and trouser pants that are also silk, but a different kind of silk, which you told me to wear. And I was just like, you know what? I look like a fucking narc.

Oh my god, my style is Prada Narc!!! This is a good roast.

I mean, you are the fashion police. Sometimes it looks great. But there's a time and a place, you know?

100-percent. Okay, a lot to process here. “Prada Narc” is going to haunt me for the rest of my life. But this was, by and large, the nicest roast, ever. So, thank you.

Dammit.

The Jedi becomes the Master.