StyleUp is Saving My Life Right Now By Telling Me What To Wear Every Day

My brain hurts -- so let's just let the cool co-founder (an ex-Jane magazine intern!) talk.
Publish date:
May 23, 2013
fashion, tech

I’ve been feeling pretty stupid lately. Not merely feeling forgetful, or making a slew of dumb mistakes. But when I sit down to write, there’s a whoosh in my skull, like a blowing wind. I search my brain for a few words, or a complete thought. Then I stare at my hand for five minutes, and usually end up watching Hulu or something.

My friends reassure me it’s due to stress from my impending move -- like my brain’s shutting off for a bit, as my mind can’t handle anymore now, thanks. I, on the other hand, blame my medication. (That’s just a new favorite hobby of mine, though.)

“Look at that weird commercial!” I laughed as I pointed to an ad on a bus shelter in the East Village last night. The two friends I was walking with were deep in conversation about things I couldn’t even comprehend. They didn’t look up. I still felt the need to correct myself. “I meant -- poster.”

One of the most difficult parts of the day when I’m feeling brain-dead, typically, is in the morning, before work, when I’m trying to get dressed. “I don’t understand this WEATHER!” I’ll yell to my roommate across my apartment (and maybe at myself.) “What does 70 degrees MEAN?”

Old me would’ve yelled at my clothing rack -- and maybe taken a bong rip -- until I gave up, threw on a maxi skirt, and rolled into work, stoned, 45 minutes late.

New me is finding solutions to eliminate stress. And, for at least one of my many issues this week, that's StyleUp.

Sick of hearing me bitch about not knowing what to wear, as climate confuses me, my roommate told me to sign up for StyleUp: Enter your email address, where you live, what your work style's like (mine's corporate casual I think?) and the site sends you an email everyday with a weather-appropriate outfit.

There’s an option to check exactly when you’ll get the email (I get mine at 6 a.m., my roommate gets hers at midnight so she can plan her outfit for the morning). And rating looks helps the “recommendation engine” (tech stuff, neat) learn your personal style.

Though there’s an option to purchase pieces from certain looks, I’ve just been literally copying the looks I get each day with pieces from my own wardrobe. Stress and time = eliminated. (In the morning. And during the day when it's rainy and cold and I'm like, "Oh, well StyleUp told me to wear a trench so...")

I reached out to Kendall Herbst, one of the two co-founders of StyleUp (along with engineer Ryan Choi) to get more info. Before heading to MIT Sloan to get her MBA -- and starting the site -- Kendall was a fashion editor.

AND GET THIS: Her first fashion internship was for Jane magazine in 2005! Small world! (Except fashion, publishing, and tech are very teeny, tiny worlds, actually.)

Let's just let Kendall talk so my brain can take a break. Go Kendall!:

"I spent five years working as a fashion editor at NYmag, Lucky, and InStyle. Around this time, Gilt was exploding, and Rent the Runway was starting too. I was inspired by all the awesome women starting their own companies, so I decided to go to business school.

"Once classes started in fall 2011, my life got a lot busier -- accounting homework, scheduling group meetings and trips, running the Retail Club... I didn't have time to read 600-page magazines every month, or flip through tons of blogs for fashion ideas. Plus, when I did have the time, the kind of fashion imagery I was seeing wasn't very helpful: Models in gowns riding horses -- not so helpful in the Boston winter!

"I started StyleUp because I wanted to give women actionable fashion advice that was personal to them. I want to help busy women enjoy fashion without having to spend a ton of time thinking about it. [Ed. note: YES THANK YOU. Now I don't have to think at all MUWAHA!]

"The kind of advice we give in our daily emails is like, it's going to snow tomorrow, here's a cute way to layer two sweaters. Or here's a chic way to infuse some style into a corporate look for the woman who works in a bank. It's advice that's really relevant and inspiring to each woman -- and you get just one look per day, so it takes like 30 seconds.

"I am really proud of the product we've built so far, but like any early stage startup, there's a lot to improve. I want StyleUp to reflect modern beauty. Aren't we all pretty bored of news sources needing to count the number of non-blondies on the catwalk?

"The first StyleUp member is one of my best friends, and her family is from Haiti. I always have her in the back of my mind when I have to spend 3x as long finding a chic look on a woman that's not Karlie Kloss-ish. So race, age, body shape, etc -- all of that needs to open up more on StyleUp. And we'll get there.

"Price too! I want to personalize shopping to each woman's budget. It sucks to see an amazing bag -- and find out it's $4K. I'd love to personalize the e-commerce to be meaningful to each person.

"Internal to the company, I want to build a solid enough startup where we can pay interns a reasonable amount of money. I hate how a lot of fashion companies expect 18-year-olds to live in NYC for the summer on either no salary or a really low salary. It weeds out amazing talent. I want to help other girls and women see business school or entrepreneurship as a viable option. Let's all lean in together because life is crazy, and we should propel each other forward.

"'Overall, I have all kinds of grand plans for why StyleUp as a company and as a product MEANS something to the world. It means everything to me. I've got to put in years and years (and years) more work to get there, and I couldn't be more excited to do it."

Follow me on Twitter: @caitlinthornton. HA, I mean, you should probably follow on Kendall on Twitter since she practically wrote this for me: @kendall_to_go. Or StyleUp: @thestyleup. Or you should just sign up for StyleUp.