Indochino is an online menswear store that makes shopping for stylish clothing as painless as possible. Men pick from a selection of suits, shirts, outerwear and accessories to choose their style, customize their choices with details like monograms and linings, and go through a quick step-by-step guide to create their measurement profile. The clothes are then made and delivered within 35 days of ordering.

“Most men need all the help they can get when shopping for their own wardrobe,” said Tom Stemberg, Managing General Partner of Highland Consumer Fund, in a statement. “By providing higher quality custom menswear at a lower cost, Indochino has revolutionized the direct-to-consumer business and become a global presence in custom menswear.”

Highland led this round and Stemberg will join the company’s board. Madrona Venture Group and Acton Capital Partners also participated in this round. Vertically-integrated e-commerce startups are taking off, as well as fashion startups geared towards men who appreciate the convenience of online shopping. Last April, online mens clothing retailer Bonobos raised $16.4 million and other startups like Frank & Oak and Trunk Club have garnered attention for making good style easy and accessible to the average Joe. By cutting out the middlemen, companies like these can offer higher quality goods at a lower cost and prove a greater layer of personalization.

This financing will be used to investment in marketing and product development. Indochina is also opening up a pop up ‘Traveling Tailor’ store in Boston, where men can be measured and styled in person. Indochino is headquartered in Vancouver, BC. It was founded in 2007 and has raised $17.25 million to date.

Photo Credit: Indochino

Google Glass got one step closer to reality yesterday with Google expanding its preorders. Now it also looks like the connected glasses are going to get more fashionable, with spectacles startup Warby Parker reportedly in talks to help style the device.

The New York Times reports that Google is currently negotiating with Warby Parker to make frames that will be a bit less geeky than what the device is currently peddling. Warby Parker is a hot e-commerce startup known for its stylish frames, so it could help make the product more palatable to people who aren’t tech enthusiasts.

Ideally, a Warby Parker line of Google Glass specs could be a popular device for the right price. Google Glass is sort of like having a smartphone on your face, with the ability to record and share what you are seeing and potentially display information over your eyes that you might want or need. Google showed off how versatile Glass can be last June, jumping out of an airplane and streaming the experience to a live audience.

Google reportedly plans to start selling Glass to the public some time later in 2013.

Check out the latest Google Glass video below to get a better feel for the experience it could provide.

Google Glass photo via Google

Zindigo announced today that it raised $4 million in angel funding.

Zindigo enables entrepreneurial fashionistas to open boutiques on Facebook and earn 40% of every sale. Users can either open a shop dedicated to an individual designer or a virtual store that carries multiple brands. Zindigo has over 80 apparel and accessories designers on the platform, and it is a compelling option for brands looking for greater exposure and distribution, users that would love to indulge their style obsession in a lucrative way, and consumers that prefer a more curated, intimate shopping experience.

It is also a compelling model for investors drawn to the innovative approach to social commerce. It is not uncommon for online retailers to offer commission to users or affiliate site for referral links, and there are other startups like StyleOwner where people can establish their own digital boutiques. Zindigo, in addition to offering a far greater portion of the sales, also has tracking and analytics tools, as well as perks like free-shipping, to optimize sales efforts.

No time are the desires for unique articles of clothing and extra cash more pronounced than the holiday season. Kareen Mallet, a former executive at luxury department store Neiman Marcus, has joined Zindigo as Fashion Director. In a statement, she emphasized the role Zindigo could play in helping small designers get their work seen.

“I have spent my career watching talented designers struggle through the challenges of building a business and developing their distribution,” said Mallet.  “Brands are looking for new customers and consumers are looking for unique brands, but distribution barriers limit the connection.”

The designers also get a cut of the sales, as does Zindigo. Partcipating brands include Be&D, Cluny, Dallin Chase, Geren Ford, Isabella Fiore, Jay Godfrey, Kara Ross, M.C.L., Nicole Romano, NoNoo, Phoebe Couture, Raoul, Orlando Santana, and Ruffian.

Zindigo is based in New York.

Rent the Runway is dressing up with $20 million in investment for its unique approach to making fashion affordable.

Rent the Runway is a marketplace where women can rent luxury, high-end clothing at a fraction of the retail price. Many women (present company included) wish for a closet filled with designer clothing, but do not have the budget to support it. This desire is particularly pronounced during the holiday season’s parade of parties.

As a young woman with a busy social calendar, I want to wear something special without emptying my bank account. However, I do not want to wear the same outfit to every event, nor do I want to spend money on multiple, cheap outfits. Rent the Runway helps me access quality, style, and diversity within my price range.

“Given the economy and the prevalence of social media, women are savvy about investing in things like fashion,” said President Jennifer Fleiss in an interview. “Everyone wants to post photos of themselves wearing designer outfits to feel like their own celebrity, but don’t want to wear those dresses again. We offer democratic luxury, so every woman can have Cinderella moments and feel beautiful and self-confident.”

The company was founded by Jennifer Hyman and Jennifer Fleiss who met at Harvard Business School. Since launching in 2009, the platform has grown to over 3 million members who have access to a revolving selection of 170 designer brands, 35,000 dresses, and 7,000 accessories.

This is Rent the Runway’s third round of financing. It raised $15 million in 2010 and $15 again in 2011 to support its growth.

Fleiss said at first it was a challenge to make older, male venture capitalists understand the product, but clearly that has changed. All the previous investors contributed to this round, including Conde Nast parent company Advance, Bain Capital Ventures, Highland Capital Partners, and Kleiner Perkins Caufield & Byers. Rent the Runway is based in New York.

Read the press release. 

The entire world is eyeing San Francisco as we continue to crush it with standout technology. The financial bets are big, the innovation is intoxicating, and the city is buzzing with possibilities. But, as you can tell just by looking around, dapper dressing is still pretty low on the priority list for many digital-minded dudes.

However, in a scene filled with ill-fitting hoodies, we’ve had our eye on a few gentlemen who are bucking this trend. The nine coolest guys in tech are keeping style top of mind while making waves in the industry. We’ve asked them to get real with us about fashion disasters, their perspectives on S.F. style, and how they’re changing the world’s idea of what it looks like to work in tech. With not a flip-flop in sight, we promise — this is geek chic at its finest.

Name: J Sider
Gig: CEO and founder of BandPage

Tell us exactly what you do.
“We help musicians set up and manage their online presence. So, if you are a musician and need to set up a Facebook page, a website, or a blog — we can help. We have over 500,000 musicians around the world that use BandPage, from musicians that are just starting out to the largest artists in the world.”

How did you get started in tech?
“I slept on a couch in San Francisco for four months, going to tech meet-ups every day, talking to over 1,000 people. Then I found an amazing engineer, Chris Tholen. We would build products every day until 2 a.m. and then sleep for a few hours and wake up and start again. It’s true, ask his patient and awesome wife, Kate.”

What is the coolest part about your job?
“I get to build stuff I love for the people I care most about: musicians. We get to change an industry with an office full of amazing people. There is music playing all day at the office, great conversations, and tons of innovation.”

How would you describe your style?
“Virginia mountain man meets urban San Francisco.”
What are your go-to wardrobe staples?
“Levi’s, flannel, and a red cap.”

Photo: J Sider kicking it in Levi’s jeans, a thrifted shirt, and that infamous red beanie! 

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My Dad does not like to shop. Twice a year, he visits a personal shopper at a department store to round out his closet and will not enter a clothing store for the next six months unless under duress. He is not alone, which is why a number of online clothing services for men have cropped up over the past year or so.

Frank & Oak, which designs, manufactures, and distributes its line of men’s shirts and accessories, has raised $5 million to dress guys like my Dad, who would rather be kayaking.

Once granted free membership, men answer a series of questions about their style preferences. They can then shop through Frank & Oak’s inventory and receive personalized recommendations. Each month, they receive a feed with new collection items and curated suggestions of what to buy.

The founders know that some male shoppers find all the choice overwhelming and just want someone to pick for them. At the same time, they won’t wear things that don’t feel right. My father is not about to wear a pair of black skinny jeans just because they show up on his doorstep.

“Our mission is to make shopping incredibly easy for men,” said CEO Ethan Song. “Going into stores and being faced with endless options is not just inconvenient, it’s confusing. At Frank & Oak, we don’t overwhelm you with endless options; we show you a handful of carefully selected styles that we know you’re going to like.”

Every month, the team presents a new collection to its members. It has direct contact with its consumers and can alter its shopping experience accordingly. This structure also cuts out the middlemen, making the clothing affordable without sacrificing quality. Items average at $50.

Frank & Oak launched in February 2012 and currently has 35 employees based in Montreal Canada. This first round of investment was led by Lightbank, with participation from BDMI and Rho Canada Ventures. It will go toward expanding the range of clothing and products offered, as well as producing more clothing to widen the membership capacity.

An array of other services out there seek to make men’s shopping as painless as possible. Trunkclub offers a personal stylist service that sources high-end clothing especially for the user. It can be pricey and does not manufacture its own line. OutfitEZ is a monthly subscription service that sends precurated boxes based on a selected profile, such as ‘Tomorrow’s Boss’ which is described as “Business Casual with confidence” or ‘Rugged Urban.’ Bombfell sends one item every month, at a regular price of $69.

Frank & Oak is part of a shift toward vertically integrated e-commerce companies that can react quickly to what their customers want. Although I am not sure how they would respond to my Dad’s love of souvenir sweatshirts.

New York fashion and beauty media company StyleCaster has acquired Daily Makeover, another New York-based digital property focused on combining beauty and technology.

As we’ve written previously, StyleCaster manages several web destinations, including StyleCaster News, Beauty High, and recently launched luxury site The Vivant. Now StyleCaster will add Daily Makeoever to its stable of sites and licence out its technology to generate more revenue. Daily Makeover’s tech allows people to try out cosmetic makeovers virtually, and it currently powers more than 30 million makeovers per month.

StyleCaster CEO Ari Goldberg said his company’s march to success hasn’t been easy and that he will keep fighting to make his business bigger. He noted that he sees a lot of similiarities in Daily Makeover, which has fought to keep expanding and licencing its makeover technology.

“Both StyleCaster and Daily Makeover are still here,” Goldberg told us via email. “Through ups and downs, booms, and recessions, these two businesses never gave up. Both of these businesses are fighters, and that’s why we will win. When you bring together two teams that have a track record with that kind of dedication, desire, and willpower — amazing things can happen.”

StyleCaster expects the addition of Daily Makeover to its sites will triple its traffic and double its revenue by the end of 2012. The StyleCaster team will expand from 25 to 40 employees, and it also plans to hire new executives and salespeople.

While the exact terms of the StyleCaster-Daily Makeover deal weren’t revealed, StyleCaster did raise $2 million in new funding led by Bo Peabody, partner at Greycroft Partners. Goldberg says the round is still open. Previously, StyleCaster raised $5.75 million in funding.

Beautiful twins photo via Shutterstock

Like floral prints, leather, and the color white, ‘democratization’ is a hot trend in the fashion world — and the internet is a strong force driving that evolution.

For this year’s series of Fashion Week events (in New York, Milan, and Paris), big name designers are holding digital fashion shows accessible to the public, not just the fashion elite. There is real time video footage of models walking down the runway. Google+ hangouts backstage with designers also provided a rare glimpse into the behind-the-scenes action. Even fashion doyenne Diane Von Furstenberg wore Google Glass spectacles to produce a first-person video of her adventures.

Democratization goes further than merely broadcasting fashion shows in new ways. Now, instead of a core group of tastemakers, social media activity reveals which collections are hits and which fall flat. Similarly, content from bloggers and Instagram is just as prevalent as content created by magazine editors and professional photographers, and can be just as influential.

Furthermore, fashion companies are using big data analytics and forecasting technology to predict trends, rather than relying solely on words from industry leaders.

This embrace of technology has been a long time coming. There are several reasons why the fashion industry has been slow to jump on the cutting edge of tech. Many designers want to maintain the prestige of their brand and tight control over how it is presented. Every detail, from the shade of lipstick to the order of the models to the lighting, is meticulously chosen, as are the members of the audience.

But that’s finally starting to change.

“Fashion Week was once only accessible to the elite,” said Eventup CEO Tony Adams. “I think the fashion industry has been slow to adopt new forms of media because initially, most designers felt that fashion is an experience that is hard to replicate online, but the abundance of online fashion portals, live streaming, and social media are making fashion more accessible than it has ever been.”

Eventup is a startup that matches events to venues. This year at New York fashion week, the company helped multiple designers plan their runway shows and published an infographic on the evolution of fashion week.

Media companies like IMG and KCD are producing digital shows that sends the glitter and drama of haute couture into living rooms, while media outlets like the New York Times and Wall Street Journal provided live stream coverage of events. Now those of us who don’t have closets full of Dior dresses and Jimmy Choo shoes can watch an event at the same time as the A-List celebrities doe. But this does not necessarily undermine a collection’s status.

“Ten years ago, the idea of someone in South Dakota watching a live stream of a runway show was outlandish,” said John Jannuzzi, a digital editor at Conde Nast’s Lucky Magazine. “Now, everyone is watching it at the same time, but accessibility does not make it less exclusive. Nothing compares to being at the actual show.”

Big data and internet broadcasting

Broadcasting event footage to the masses opens collections up to tremendous amounts of discussion across social networks. People of all backgrounds and ages can offer their opinions, but the power of social media means these opinions actually have an impact. Viewer reactions to runway outfits can indicate what themes were the most well-received and popular with potential consumers.

Editd is a big data company that provides actionable information for fashion brands. It not only analyzes the amount of traffic surrounding designers or trends, but also looks at the sentiment surrounding data points. According to its reports, New York consumers like feminine and retro aesthetics, while Londoners dislike the presence of dip-dye.

Another fashion big data company, The Whispr Group, provides a “social media intelligence service” to help designers assess the effectiveness of their social media efforts. The team created an infographic about which designers “stole the social show”, with Victoria Beckham, Marc Jacobs, and Diane Von Furstenberg rising to the top.

“Brands can see which hash tags drive the most engagement,” said Whispr exec Linda Harleman. “They see the top themes and looks people were most excited about, and maybe use that to develop new strategies and inform their content calendar.”

Reinventing fashion shopping

For some of the most luxe, avant-garde design houses, paying attention to social media may not be a top priority. However, brands marketing their clothes to customers outside of a wealthy minority have to adapt to a new paradigm for exposure.

“An advantage of social media is it exposes a more widespread audience to brands at fashion week,” said Adams. “Twitter and Facebook are key platforms for customer sales and engagement, as well as driving traffic to brands sites. Also, Instagram has been a great platform for designers to test their new designs by posting a picture and tracking how often it’s “liked” by the brand’s followers. Social media should be a personal and authentic experience.”

Startups have also revolutionized the way shopping happens at fashion week. Before, standard practice was to sit in the audience, frantically take notes as models flit past on the runway, and then scramble to place orders and be put on wait lists for items. This year, there are apps for show attendees dedicated to documenting looks, as well as for live blogging and managing hectic schedules.

Social commerce site Lyst lets users browse through the inventories of thousands of brands and add desired items to their “list.” Users can also subscribe to feeds centered around designers, bloggers, stores, magazines, and their friends. The company offers a runway tracking feature where fashionistas can add make a list of their favorite looks and receive alerts when they become available. This year, Lyst offered “Live Lysting” with style mavens Nina Garcia and Olivia Palermo, as well as the Google Plus hangouts with big names like Rebecca Minkoff.

“Lyst is all about empowering the consumers,” said head of business development Hilary Peterson. “The hangouts gave them unprecedented access and a glimpse of the backstage atmosphere, while also allowing them to ask the designers anything they wanted live before the show. So we really felt like we were giving consumers, who aren’t normally at fashion week, access to something special.”

Fashion’s tech invasion

Technology infiltrated fashion week in other ways. Digital prints were a popular trend, as were retro aesthetics reminiscent of Instagram. The internet also provides a useful tool for fledgling designers to cheaply produce and publicize their own fashion shows and potentially rise to stardom. Microsoft even partnered with Bloomingdales to create a high-fashion, high-concept, high-tech dress, complete with circuit boards, and style startups were able to get off the ground amidst all the noise.

For this grown up little girl who loves both fashion and technology, this is a trend I am thrilled about.

Fashion and beauty-focused media company StyleCaster has launched a new web destination called The Vivant, a site dedicated to young people obsessed with travel, luxury, and “the good life.”

The Vivant becomes the third property in the StyleCaster family after StyleCaster News and Beauty High. StyleCaster News focuses on fashion while Beauty High covers makeup and hair. The Vivant tells all those fashionable StyleCaster readers places to go, tips to get in to the best parties, and ways to live big even if you’re not a millionaire.

“Departures is great if you’re 50,” StyleCaster CEO and cofounder Ari Goldberg told me. “Condé Nast Traveler is great if you have a third house in Italy. What about people who younger and still want to enjoy luxury?”

Goldberg said the target demographic of The Vivant is young urban professionals “between the ages of 24 and 34,” with some folks outside that range. “We want to fulfill the needs of the StyleCaster girl,” Goldberg said.

The Vivant’s site, which went live today, features content including an article about New York Fashion Week party crashing tips, a list of luxury hybrid cars, and a profile of Graydon Carter’s new Beatrice Inn restaurant in New York’s West Village. Ideally, the site will be updated every day with more content like this.

New York City-based StyleCaster was founded in 2009 and redesigned its site recently with heavy influence from Pinterest and Tumblr. The company has raised a total of $5.5 million in funding to date. Its last funding round in November 2011 came from folks including Zynga chief mobile officer David Ko and former MySpace CEO and Zynga exec Owen Van Natta.

Top photo: The Vivant
Homepage photo: Holly Owens/Instagram

Fashion startup The Cools publicly launched today and announced $2.5 million in funding led by media mogul and MTV founder Bob Pittman. Described as a mashup of a social network, blog, and e-commerce, the site is a curated marketplace that allows users to buy, sell, and share whatever defines cool for them.

For those who have dreamed of being an editor at Vogue or are trying to gain brand recognition, The Cools serves as an easy outlet. Users can do anything from showcasing their personal designs to creating a style blog to buying “cool” items on the spot.

Rather than waiting for recognition from mainstream fashion magazines, individuals, designers, brands, and boutiques of any size can use the platform to express their editorial vision and build an audience for their products. On the other end, The Cools presents consumers with suggested products, based on the idea that an individual’s style, taste, and personality should influence what they see while shopping.

The Cools is advised by major names from across the fashion industry, including LVMH’s Antoine Arnault, Fab.com’s Beth Ferreira, Italian icon Lapo Elkann, and designer Erin Fetherston. It was started in NYC in 2011 by Parisian entrepreneur Olivier van Themsche.

Fashion and style media company StyleCaster is just a few days away from launching a redesigned site that’s heavily influenced by  social media darling Pinterest and blogging service Tumblr.

StyleCaster’s main website, Stylecaster.com, and its social channels offer news and features related to style, fashion and celebrities, and the company focuses intently on fostering conversations around those topics. Stylecaster.com and sister site Beautyhigh.com attract more than 2.5 million uniques visitors per month, and the company sells ads through other blogs as well. The company also offers proprietary ad platform called Style as a Service that helps offer ad placement advice.

“When I wake up in the morning, I go to ESPN; that’s my homepage for sports,” StyleCaster CEO and co-founder Ari Goldberg told VentureBeat. “There really isn’t anything like that for style. I want StyleCaster to be the homepage for style.”

Now the site will take its next logical step to offer access to curated fashion news stories and products. It’s doing that with a homepage that mimics the design of Pinterest. There will also be a brand-new news page that delivers fresh editorial content daily on beauty, fashion, and pop culture.

Every piece of content on the new StyleCaster site will feature an easy-to-click “Love” button, a feature that already appears on StyleCaster but now will be much more prominent. The Love button will also be available to other publishers and e-commerce services for installing on their own sites in the very near future.

“This is the product we’ve envisioned for the three and a half years we’ve been working on the site,” Goldberg said.

New York-based StyleCaster was founded in 2009 and has raised a total of $5.5 million in funding to date. Its last funding round in November came from the likes of Zynga chief mobile officer David Ko and former MySpace CEO Owen Van Natta.

Finally, let’s compare the looks of the current homepage to the upcoming news page, which share the most similarities. Take a glance below at the current homepage, which does its best to blend news, features, and shopping together:

And now take a look at the new StyleCaster news page, which is essentially a well-designed news blog inspired by the look and features of Tumblr:

What do you think of the upcoming redesign?