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5 Startups Bringing Personal Styling to the Masses

Styling services aren't just for fancy ladies anymore.

When you think of personal stylists, you tend to think of the fashion geniuses available for hire to a very small subset of the population — i.e. the very famous and/or the very wealthy. But a new generation of startups are making personal shopping advice more accessible than ever before, and significantly more affordable. These companies combine tech smarts and that indispensable human intuition factor, equipping their personal shoppers with algorithm-driven tools that act as shortcuts in helping them find the clothing their clients will like best and free them up to work with more customers at once. 

Meet the five personal styling startups you need to get on your radar — and maybe in your shopping arsenal — ASAP.

Keaton Row

Founded: 2011
Headquarters: New York
Funding: $3.5 million in seed funding from Menlo Ventures and Rho Ventures​​.
The lowdown: Founded by Harvard Business School grads Cheryl Han and Elenor Mak, Keaton Row connects customers with personal shoppers – everyday fashionistas who apply to work on commission for the startup, often as a way to make some extra cash. First-time shoppers take an onboarding quiz, giving Keaton Row data on their taste, fit preferences and body type, and they're matched with a stylist to work with one-on-one through personalized lookbooks and live chat. Since this is an entrepreneurial endeavor for many of the stylists, the site has been working on developing its dashboard and outfitting it with business management tools to help stylists grow their own businesses.

Stitch Fix

Founded: 2011
Headquarters: San Francisco
Funding: $16.75 million in Series A and Series B funding from Bill Gurley of Benchmark, Steve Anderson at Baseline, Lightspeed and Western Technology Investments.
The lowdown: As with Keaton Row, customers entering Stitch Fix for the first time are asked to complete a 10-minute style profile, which the company's stylists use to create a box of five items costing around $55 apiece. Shoppers then schedule a delivery, keep what they like and send back what they don't with a comment card — that helps the stylists figure out what to send in their next shipment. Customers also get to schedule new "fixes" for as often as they'd like, either manually or automatically, so that they can get a wardrobe refresh every 2-3 weeks, month, or every other month.

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Trunk Club

Founded: 2009
Headquarters: Chicago
Funding: $12.4 million, acquired by Nordstrom in July 2014.
The lowdown: Like Stitch Fix for men, Trunk Club was founded by Brian Spaly, one of the co-founders of the men's clothing startup Bonobos. Shoppers work with personal stylists who help them figure out what to buy and ship the clothing to them; from there, guys try it all on at home and send back what they don't want to keep. Clearly the idea was a pretty compelling one: Just last week, Nordstrom announced that it had acquired Trunk Club for an undisclosed sum, representing an investment in new models for selling menswear.


Founded: 2012
Headquarters: Tel Aviv
Funding: $400,000 raised from founder Gil Hirsch and Tal Simantov, founder of 5MIN.
The lowdown: A participant in the 2014 New York Fashion Tech Lab, Stylit operates on a similar model to Stitch Fix and Keaton Row but emphasizes a higher level of market knowledge when it comes to their roster of personal stylists, who earn cash on a per outfit basis rather than on commission. Unlike Keaton Row's more amateur shopper base, Stylit focuses on hiring bloggers and stylists who already work in fashion.  

Share Some Style

Founded: 2013
Headquarters: San Francisco
Funding: $100,000 in seed funding raised from 500 Startups.
The lowdown: One of the many startups framing its product as an "Uber for [name of industry here]," Share Some Style is all about matching customers with freelance stylists in their local area. One of the services that focuses heavily on editing a customer's closet before getting to the shopping phase, the stylist will come over (or video chat in) to take a look through their client's existing wardrobe, dividing it into piles for donating, keeping and maybe keeping. From there, the personal shopper will help figure out what the client needs and stays in touch for monthly check-ins. Frankly, this service might even be helpful for those of us who have trouble cleaning out our closets every season. 

Top photo: Trunk Club