YouTube Star Grace Helbig Manages to Make the Darkest Sides of Fashion Funny

Grace Helbig is funny, pretty, and relentlessly positive — and yet, she’s honest and unpolished enough that her millions of YouTube subscribers feel like she’s completely relatable. At 30, Helbig calls herself “the Internet’s awkward older sister,” but despite that low-key branding, she’s achieved successes most actors and comedians could only dream of: Her podcast, Not Too Deep, debuted at No. 1 in iTunes, and her first book, a tongue-in-cheek how-to about acting like a grownup called Grace’s Guide, was a New York Times bestseller.

Today, Helbig releases her second book, a humorous style guide called Grace & Style: The Art of Pretending You Have It. In it, she discusses a former eating disorder, details an inventive saga about a pair of sentient sweatpants’ collegiate adventures — the sweatpants matriculate to the prestigious Mall of America — and manages to dole out some practical and empowering advice.

She talked to us about choosing to open the book with the story of her eating disorder, and having a love/hate (well, more of a love/eye roll) relationship with fashion and beauty.

Yahoo Style: I thought it was cool that you started the book opening up about your eating disorder. You wrote that it was a tarot card reader who inspired you to do it?

Grace Helbig: Yeah, it was a tarot card reader that I’ve gone to a bunch and she’s really wonderful. And she didn’t necessarily say, “Hey, talk about your eating disorder.” I just talked to her about the book and she pulled this card, and she said, “This card says you’re going to have to open up a little bit more. You’re going to have to pull the curtain back and let people see a little bit more of yourself,” which really struck a chord because there was this little voice in the back of my head wondering if and when I would talk about that time in my life and when would it be most appropriate to.

It’s a little strange sometimes when you talk about your personal struggles because you don’t want it to come across as narcissistic, as weird as that sounds. You don’t want it to seem like, “Pity me! Look at me! Look at all the hardships I’ve been through.”

Instead I wanted to use it as a just kind of this pillar that says, “Hey, this might be relatable.” Because in my past I’ve found a lot of comfort in relating to people with similar struggles, and it also gives you a context for how I’ve learned to see body image and fashion and beauty.

So you hadn’t talked about it before the book, publicly?

No, I hadn’t and the book felt like the right place to. I’ve had every opportunity to mention it in a video over the past seven years, and it just never felt right. And the book felt like a very personal, intimate way to write down exactly what I wanted to say about it, and present it in a way that I thought would be most effective for people to read.

When did you think about your eating disorder and realize, “This is something that can be funny?”

It took such a long time to realize that it can be funny.

It helped me when I started getting into comedy and started performing, and being able to put into a creative space thoughts that I was living alone with in my brain.

I realized that that was really important: To take these dark moments and struggles, these moments of very deep depression and turn them on their head and realize how ridiculous I myself am voluntarily making myself.

It’s very liberating to think, “Oh, my brain is being ridiculous. My concept of myself is absolutely hilarious. And the fact that these fabrics and clothing and colors can define me or change me or cause someone to judge me differently is kind of hilariously absurd. So being able to carry that message through is important for me. Especially, there’s a whole lot of pressure on women from society from a very young age, so I just want to be some voice that’s there to say, “Hey, all those things that people are telling you you should do, and how you should look, you don’t have to. And you’ll still, like, be alive and thriving and a great human being.”

Do you really believe in tarot card readings and stuff like that?

I do. I’m a pretty gullible human being across the board. Ghosts terrify me because I think they’re real. Aliens exist in my universe. And tarot and astrology in general I find so fascinating because there have been moments that kind of moved my life forward in a positive way that have come out of tarot card readers.

I love that in the book, you were like, “I’m not necessarily an expert and I just have fun with style.” Do you feel like if you could just be a floating head and not worry about style or fashion or makeup, would you? If we were all just brains in jars?

Yeah! Even today, as I look down at myself, I’m wearing a sweatshirt with stains on it and my dog’s face ironed onto the front of it, and then sweatpants and a pair of socks that my friend got me from Norway. And so there are moments when you wish that you could just walk around wearing bed sheets all day, every day and that that was fine and passable. But then there’s moments where you really love getting dressed up, and you love hair and makeup and you love trying different things, and I think that’s what’s really cool about style — that you can have that spectrum. That you can have days where all you want to be is a head in a jar, and you don’t put any effort into it, and you have days where you really want to try and make something happen.

Do you feel like there’s an ethical responsibility to find out where your clothes came from?

I do. It’s really tough sometimes because if you’ve been used to shopping at a really cost-effective store and then you look into some of the more not attractive things about the company, then you’re kind of stuck in a hard place of, “Well, I can’t afford the stuff that maybe these more socially conscious stores are offering, but I don’t want to be aligned with any of these ideas that this company has,” so making your own clothing kind of eliminates all of that.

I recently — and there’s a small section in the book about it — have gotten huge into DIY. You can make really great-looking, expensive-looking shirts and accessories that you see in these Brandy Melville stores or Urban Outfitters, yourself, at home, just by buying a couple things at a craft store. One of my favorite things is to buy a package of small men’s white Hanes T-shirts and then get a bunch of iron-ons. I literally made a T-shirt last night that I’m bringing on tour.

They’re great because they’re really cost-effective, and if you don’t like them, you can replace them or change them for not a lot of money, and you can go online and find a lot of different designs and iron-on things. It really becomes overwhelming, the amount of choices and control you can have in that area. So I highly recommend putting a little time and effort into creating your own look.

What’s the shirt that you made last night that you’re bringing on tour?

I made a shirt that says, “Dibs on the piano player.” I saw a bunch of shirts online that said, “Dibs on the drummer and bassist” and things like that, and I was like, “Oh, I’m gonna make one of those.”

I just got myself a sewing machine, which I’m really excited about. I’m kind of regressing in technology, which I think is cool. I also think it’s great to give you a break from the Internet, which is really nice sometimes to have hobbies that are offline.

Have you sewed anything yet?

I made a hamburger fabric pillow, which I am very proud of. I used to sew when I was in high school. I remember I made one of my homecoming dresses and it was not well done, but I wore it because it felt responsible to, because I spent so long making it, and then that sort of faded away. So I’m really excited when I have more time after book tour to actually make stuff. I think it’s so cool when people actually make stuff that they use on a daily basis or have in their lives.

You sometimes use stylists for big events. Do you have one for your book tour?

For this tour, I’m trying to do a lot of it myself: Pick out my own clothes and do my own hair and makeup, and really kind of present myself as myself, which I’m really excited about. Because the other reason that I wrote this book — other than thinking that beauty is ridiculous — is that I love clothing and makeup and jewelry and accessories and all of that. As much as I think it’s hilarious, I love playing around with it because I feel like it’s this open-ended playground that you get to create things in, and there are no real rules. It’s just what you want and like and feel confident and comfortable in.

Are there any trends that may be good for somebody else, but you absolutely cannot?

This isn’t a trend, it’s a life staple I guess, but high heels I just haven’t mastered yet. I’m 5’9 in life, so wearing high heels feels a little like I’m unintentionally saying, “Hey everybody! Look at me! I’m even taller than I already was!” I also look like a baby deer on an ice rink when I wear heels. The struggle is very, very real. I want to master those at some point, and be one of those confident women that I always see walking around New York City effortlessly in 6-inch heels. But at the end of the day, they’re really painful, so I try to rationalize, “Do I really need that?”

This interview has been edited and condensed.

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