As the weather cools down, shoppers review their closets, looking to fill any gaps in their own wardrobes and preparing their children to go back to school. Direct-to-consumer apparel companies — which bypass traditional bricks-and-mortar stores — evaluate trends in shopping habits and find a way to make tasks easier on consumers.

Three startups are using technology and integrating customer feedback to do just that. One helps men buy unique, perfectly fitting shirts; another looks to easily fill what may be a guy’s most important (and most ignored) drawer; and a third assists parents in properly sizing their kids’ feet to make online shoe-shopping easier.

Every great outfit starts with what goes under it, but Laura and Michael Dweck (29 and 31, respectively) know that most men don’t want to spend a lot of time and effort shopping for socks and underwear. So in 2015, after a post-honeymoon fight over Michael’s overstuffed underwear drawer, they started Basic Outfitters, “an online destination for men to refresh their basics drawer in under two minutes,” says Laura, the creative director. For $60, customers can select a pack of socks, a pack of underwear, a pack of T-shirts and a “wildcard basic” — jogger-style pants or an extra set of socks, underwear, or tees. (The success of the company — it now has a team of 10 working out of its office at WeWork 135 Madison Avenue — landed the founders on the Forbes 30 under 30 list.)

“All couples have the same complaint about a significant other’s drawer,” says Laura Dweck of Basic Outfitters.

Basic Outfitters quickly learned customers couldn’t be grouped into “basic” or “fashion” categories, so the wares come in a variety of styles. Even if a guy initially chooses plain socks, Laura said, he’ll often go for a bonus pack of the popular “micro-conversational” prints for socks or boxers, which feature prints like motorcycles or palm trees. And sometimes male stereotypes do turn out to be correct: Basic Outfitters’ customers can’t get enough blue, but yellow regularly remains on their virtual shelves.

Laura has learned perhaps more than she ever expected to about men’s underwear preferences — Basic Outfitters followed early feedback requesting boxer briefs with a fly opening, and their popularity persuaded the company to develop more such styles.

Taking fashion risks

Woodies Clothing, which sells custom button-down shirts (starting at $85) and chinos (starting at $98) from its website, also discovered that men are willing to take fashion risks, even with  collared shirts. While Woodies’ bestsellers include straightforward no-iron blue and white button-downs, a flamingo-print shirt sold out in its first run. “That’s something we were not expecting,” says founder Jacob Wood, who works from 175 Varick Street in Lower Manhattan. Since moving into WeWork in 2014, Woodies has expanded to a staff of five.

Customers may be pleasantly surprised by how extensively Woodies has streamlined its process of ordering a custom shirt, which involves a dizzying number of options for collars, cuffs, and pockets. When Wood, a former buyer at Macy’s, founded his company in 2014, early iterations of the site suggested that customers use a tape measure and watch videos to take their measurements. Needless to say, that idea didn’t fly.

With height, weight, and average shirt size, we can extract all your measurements and send you perfect-fitting shirts,” says Jacob Wood of Woodies.

Now, the 31-year-old entrepreneur says, “we have an algorithm: With height, weight, and average shirt size, we can extract all your measurements and send you perfect-fitting shirts.” Pant sizes can similarly be determined when the customer provides his waist size.

Kicking around an idea

One startup is trying to make shopping for kids’ shoes easier for parents. Growing kids’ sizes are always changing, and it can be difficult to get those growing kids to cooperate in a brick-and-mortar store. So Jenzy‘s app directs customers to snap a picture of a child’s foot next to a credit-card-sized card (preferably one that doesn’t show financial information, like a library or store loyalty card). The app, which serves kids up to 6 years old (there are plans to extend the age range), then recommends the best sizes for the child in various brands and styles, including those from well-known manufacturers like Keen and Pediped.

“We’ve been live in the App Store for about two months and have about 1,500 downloads,” says Carolyn Horner, who co-founded the company with Eve Ackerley. The two are very pleased with their return rate.

It was not the most obvious path for the two child-free 20-somethings, but as they thought about starting their own clothing company, they kept hearing from friends who were frustrated with buying children’s shoes online. They realized that they could simplify the process.

Development of the app involved a lot of trial and error for Horner and Ackerley, who met teaching in China after college and are now based at WeWork 1601 Market in Philadelphia. Well before they were ready to send it to mommy bloggers for review, they found a surefire way to entice fellow WeWork members to test-drive the app in the building’s common areas. “We’d bring doughnuts to the beta test,” says Horner. Not only did they meet parents who offered suggestions, they got acquainted with a graphic designer who ended up doing the UX for their site.

The founders of Basic Outfitters also picked up tips from the WeWork community. One particularly lucky break, Laura Dweck says, was meeting a video producer in the WeWork building who agreed to shoot a series for social media to build buzz. “He put together some incredible footage, taking influencers around the city to film people going through their life wearing our basics,” she says.

The experienced producer, who’s done work for brands such as Bravo and Chevrolet, simply believed in the product. Laura says she recalls him saying, “I’ll do this for you guys — let’s have some fun.”

Dweck says the producer gathered some social-media influencers and filmed them going about their days in Basic Outfitters attire. Soon the company was getting notes from people who loved the clothing, including some women who wanted it to expand its product line.

“All couples have the same complaint about a significant other’s drawer,” says Laura. “We started the company to help out men, but now the demand for a women’s drawer is off the charts.”

Black Twine, a New York-based “event-inspiration” website that’s on a mission to cure Pinterest fatigue, was just about a year old when its co-founder, Anne Hyun, a member in WeWork 222 Broadway in New York, sent a cold email to a woman she’d never met. Until then, Hyun’s fledgling business marketed to busy millennial moms, supplying them with party “blueprints”: gorgeous photos paired with lists of what to buy (many items in the inspiration photos are shoppable), menu ideas, and a suggested timeline for event prep and execution.

On a hunch, Hyun reached out to Eva Chen, Instagram’s director of fashion partnerships, who was about to release a children’s book, Juno Valentine and the Magical Shoes. Hyun wanted Black Twine to work on an event for the book’s launch. “We’ve been longtime fans of Eva,” Hyun says. “She’s such a role model for women, but she’s also a mom, and my two co-founders and I are all moms. [And then there’s all] she’s done for the Asian community.”

It was a risky move—Hyun had admired Chen only from afar—but it worked.

For the month of November 2018, the front windows of Books of Wonder, a children’s bookstore in Manhattan, featured a dramatic jewel-toned archway of balloons surrounding a cutout of Chen’s character, Juno, all designed by Black Twine. “We had never actually done a window before,” Hyun says of her company’s partnership with Chen, which also included styling her book-signing event at the store. “But for us, it was about being able to work with someone who was really inspiring.”

(Above) Anne Hyun, co-founder of Black Twine. (Top) Hyun and Eva Chen, Instagram’s director of fashion partnerships, in front of a window display at New York’s Books of Wonder.

She stays true to that entrepreneurial spirit while running Black Twine, which she says is a lot like planning one big party. “Managing a business and planning a party both come down to time management,” she says. With event planning, she explains, there are five different things you need to worry about: the decor, the guests, the food, the beverages, and getting all the vendors and different pieces in place. Similarly, she can break down her business into specific tasks—which she then has her team divide and conquer. “Like with event planning, if you try to do it all on your own, you’re going to be in a world of misery,” Hyun says.

Her team is also not afraid to hire others for certain to-dos. “It took us a long time before we were able to say, ‘Oh, we’re not going to be the ones who put every single product on our site,’” says Hyun. “We’ve gotten more comfortable outsourcing different pieces of work as we’ve grown.”

And when they want to invite someone new to their party (or, um, business), Hyun isn’t afraid to send a cold email. “The one thing that we’ve learned on this entrepreneurial journey is that you have to make your own destiny,” Hyun says. “A lot of the successes that we’ve had have come from that same story, just trying to see what might be out there and giving it a chance. A lot of times it doesn’t work out, but the one time it does, it’s someone like an Eva, which is amazing.”

Hyun’s holiday party survival plan

Keep decor simple. “Place a garland down the middle of a table. It really just makes the table pop.”

Tweak the traditional palette: “One of the color combinations we used this year was sage and wine, which was a play off of red and green. It’s a bit more subtle.”

Ask people to bring booze instead of dessert. “If it doesn’t get used, unlike dessert, it can be saved for your next party.”

Be a good guest. “RSVP promptly. And if you think you can’t make it, a quick ‘No’ is better than a long ‘Maybe.’”

 

A few weekends ago, I was at my business partner’s birthday gathering, lightly facilitating some sharing of his impact—what we appreciated in Edmond, what we saw in him that he might not see in himself. A friend of his commented that most people don’t get this level of appreciation and celebration reflected back to them until they are dead. At funerals, people give themselves permission to bring their emotions, to reminisce about favorite memories, to share the life-changing impacts that person has had on them. It feels cathartic and connecting—but the person who has passed isn’t hearing a word of it.

Why we should skip ahead to the good stuff

Too often, we wait until there is an ending or closing to say kind words, or we don’t give appreciative feedback at all. The ending doesn’t have to be death—it might be when a beloved employee announces she’s leaving a job. Heartwarming emails pour in in response to the farewell email, or some words are said at the company all-hands, or people write emotional notes of appreciation.

When I left a recent job, I received brief but beautiful emails from people I had interacted with only once or twice, sharing that even in their different function, they were inspired by seeing me show up as a senior woman at the company. I hadn’t known that. One of my direct reports showed up a few minutes late to our last one-on-one because she was writing a letter—a handwritten letter! I was also presented with a foam board with more notes from the engineering team and other coworkers.

Take the first step in creating a culture in which sharing appreciation and gratitude in the moment is as natural as showing up for daily stand-ups or checking email.

I treasure those words. They reflect to me what I already know, which is that in an imperfect system, I have lived and acted true to my values and what long-term success means to me. At the same time, I wonder what might have been different for me if I had deeply known the appreciation throughout my time there.

The impact of appreciative feedback

A few months ago, Edmond and I conducted a few dozen interviews to find the patterns in frustrations, pains, hopes, and dreams of engineers, tech leads, engineering managers, CTOs, and VPs of engineering. What struck us is that so many people cared deeply about doing well and were trying to do their best, but we heard this over and over again:

“I don’t even know if I’m doing a good job.”

When I reflect on moments in my own career that I’ve received meaningful appreciative feedback, a few come to mind. In written feedback at Google, at a time when I struggled with a feeling of having “snuck” in through their internship program (rather than the normal full slate of rigorous interviews), my manager told me the work I was doing was on par with what was expected of more-senior engineers. That gave me a concrete calibration of how I was doing, so I was able to leave behind a lot of those feelings of uncertainty. A year or so after I left Google, I had lunch with a senior engineer who had been my mentor there. He mentioned in conversation that he felt like my career was a rocket ship and soon he would see me as a CTO of a large tech company. He showed me a glimpse of how he saw me as a leader before I saw myself that way.

There was also the time after I returned from my second maternity leave. I felt like I was doing all right, and as I transitioned from four days a week back to five, my manager told me, “It feels like after your maternity leave, you leveled up a huge step. I bet a lot of people didn’t even know you were working only four days a week.” The impact was that I had a better sense of the perception people had of me and my work—and that rather than just doing all right, I was kicking ass.

In each of these instances, something that was clear as day to the other person was obscured for me, and by sharing what they had seen or noticed in me, it shifted how I viewed myself.

Kicking off the gratitude loop

Companies are starting to catch on to the importance of expressing gratitude. Anil Dash, the CEO of software company Glitch, wrote on Medium about how Glitch fosters a culture of gratitude, and Camille Fournier shared how they did this at Rent The Runway. And Jen Dennard of Range Labs, a company that facilitates better communication and strengthens relationships among teams, wrote about building a culture of gratitude through high frequency and gratitude catered to each individual. Edmond and I try to express gratitude when we feel it and also reflect in our monthly debriefs with a prompt around what we’re grateful for.

When I started training to become a coach a year ago, the coaching skill of “acknowledgment”—noticing something positive about the other person and saying it to them out loud—was the most difficult for me. It felt awkward, inauthentic, contrived. Positive feedback in the form of “good job” felt like a pat on the head—condescending, almost. I imagine it feels that way for many people—and so we shy away from it, hoping that people already know what we appreciate about them.

I’ve found that more-specific prompts guide me and make it feel more structured and less awkward to share appreciation and gratitude.

  • What quality do you see in this person that they might not see in themselves?
  • What is the most noticeable change you’ve seen since you started working with this person?
  • What qualities do you most appreciate about this person? What do you see as possible for them if they lean into these qualities more fully?
  • What is your favorite memory of this person?

If you want this type of feedback, ask for it. Before your next one-one-one, take a moment to consider these prompts and share a piece of appreciative feedback. And then, in whatever way feels comfortable for you—perhaps in the same meeting, or in a Slack thread or email request—tell people that you’re looking to better understand your strengths and the impact you have on the those around you, and would love if they could answer one of these prompts. Take the first step in creating a culture in which sharing appreciation and gratitude in the moment is as natural as showing up for daily stand-ups or checking email.

Jean Hsu is a cofounder of Co Leadership and a member at Berkeley’s WeWork 2120 University Ave.

Celebrity stylist Karla Welch knows the importance of having a style uniform—and what happens when you try to fight it.  

Welch, dubbed the No. 1 power stylist by The Hollywood Reporter—with clients including Amy Poehler, Ruth Negga, Karlie Kloss, and Zooey Deschanel—recently booked a crack-of-dawn flight from Los Angeles to New York for an event at WeWork 205 Hudson. Bleary-eyed at 3:30 a.m. and prepping for her flight, Welch packed exactly one outfit: a dress. At the last minute, she threw in a favorite pair of jeans. Just in case.

When she landed in New York, she slipped on the dress to wear to the panel discussion about WISHI, the on-demand personal-styling platform she co-founded with stylist Cleo O’Hana. But the dress was all wrong, she says. Backup jeans it was.

Celebrity stylist Karla Welch’s own style uniform consists of three items: jeans, a blazer, and a white T-shirt.

That’s the power of a personal style uniform. “It’s a security blanket,” says Welch, who wears a white shirt, jeans, boots, and blazer during most of her nonstop days spent styling clients, consulting on advertising campaigns, and designing custom pieces for Justin Bieber’s world tours.

There’s a reason uniform dressing is catching on: When you streamline one aspect of your life, it frees up your brain to focus elsewhere. When you’re busy or building a company from the ground up, says Welch, “your mind is needed for other things.”  

At WeWork, Karla Welch shared the stage with fashion names like WISHI cofounder Clea O’Hana (left) and B Sides Jeans cofounder Stacy Daily (right).

Famously, Mark Zuckerberg, Steve Jobs, and Barack Obama have all admitted to wearing nearly the same outfits every day; now entrepreneurs and ambitious workers are following suit (while ditching the suit). How to begin? First, take a deep breath. “The thing is, it’s just clothes,” Welch says. “You don’t need to stress out.”

Keep it supersimple. Ask yourself, What are you looking for? advises Welch, who says it’s the first question she poses to clients. For example: “clean lines, not too fussy, something to move around the city in.” Creating a style target helps narrow your options. Welch’s own uniform consists of three items: jeans, blazer, white T-shirt. Yours could be a slight variation: stylish trousers, say, or sweaters during the winter.

Consider your days. Are you in and out of meetings? Does your commute feel like it’s 100 degrees, even in the winter—except when it’s not? Your uniform should be adaptable and feel comfortable in a variety of situations. “A uniform is a time-saver so you can do better things,” Welch says. It should never be a source of worry.

Start with what you have. Uniform dressing seems like a minimalist endeavor, yet it’s easy to think you need to buy a new wardrobe. Don’t, says Welch, who advocates wearing pieces for years. Start by shopping your own closet. It’s less expensive and more sustainable—plus, creating a style identity from familiar pieces you already own makes it more likely you’ll stick with it.

Ask one crucial question. Pick items that make you feel powerful and build from there. Ask yourself, “Do I feel good in this item?” If the answer is yes, add it to your rotation. If the answer’s no, consider donating it.

Look to the greats. Channel inspiration from artists, cinema, and celebrities. Rei Kawakubo of Commes des Garçons dresses almost exclusively in black, save for the occasional white shirt. And the artist Georgia O’Keeffe was notoriously rigid with her self-created wardrobe—so much so that her iconic androgynous silk, cotton, and wool outfits have been showcased in museum exhibits.

Solicit a second opinion. If you’re at a loss, hire an expert. It might be a better use of your time than opening 47 shopping tabs in your browser and searching for the right piece. On WISHI, each user is matched with a professional stylist. You send photographs of your wardrobe, and the stylist sends back suggestions from your own closet and from online stores.

Beat back boredom. Growing up, Welch wore a school uniform, but instead of resenting the predictability and sameness, she says, “it pushed me to be creative.” The same goes for an adult uniform. “The goal is to feel confident, not bored,” she says. “It takes a remarkable amount of confidence to wear something over and over again.” And if repetition can breed success, then a uniform could be your strongest style move yet.

Photos by Lori Gutman

Looking for one-stop shopping for everyone on your list? We’ve gathered together a few dozen of our favorite gifts from WeWork members that will satisfy your fitness-obsessed mother, coffee-loving spouse, bookish nephew, world-traveling friend, or workaholic boss without putting a dent in your wallet.

For the dreamer

Blox party: The GoldieBlox Craft-Struction Box is as much for big kids as little ones. The 275-piece kit, created by the member company at WeWork 1111 Broadway in Oakland, California, was designed to disrupt gender norms by introducing girls to STEM concepts like prototyping and problem-solving. Don’t bother looking for instructions—the only rule is to follow your imagination. $35

Totes amazing: Each of the memorable quotes on Time Travel Mart’s Student Quote Totes was written by a young author in 826LA, a nonprofit writing and tutoring organization in Los Angeles based at Pasadena’s WeWork 177 E Colorado Blvd. Gift the bright red bag to the budding writer for their manuscripts and books. $12

Best bud: Think too hard about the magic behind WinkyLux Flower Balm, made by a member based at London’s WeWork North West House, and you might go insane wondering how exactly they get that tiny chrysanthemum in the center—or how a clear balm can transform into the most flattering shade of pink ever once it hits your lips. Sometimes a little mystery is a good thing. $14

Written in the stars: Each set of Whiskey River Soap astrology pencils is filled with fun reminders of an astrological sign’s personality traits, from Pisces’ spot-on assessment as a “stray animal collector” to Capricorn’s simple and true description, “bossy AF.” $11

Color story: Help a friend fight blank-wall boredom with this limited-edition Mike Natter “Crayons” print from Art Sugar, an art collective based at New York’s WeWork 205 Hudson that gives a platform to underrepresented artists with large social-media followings. Feel-good bonus: At checkout, choose which charity will receive 5 percent of your buy’s proceeds. Starting at $20 without frame

For the adventurer  

Travel buddies: Ditch your long-held assumptions: Compression socks aren’t just for ultramarathoners and grannies. The tight fit can actually improve your blood and lymph flow if you sit a lot at work or are taking a superlong flight. These stylish versions from Comrad are the kind of socks that anyone would be happy to unwrap. $48 for three pairs

Quick-change agent: This nifty five-in-one universal travel adapter, which includes a USB port, is a lifesaver no matter where in the world you find yourself. The Flight 001 team, which works out of WeWork 109 S 5th St in Brooklyn, color-coded each adapter so that getting connected in your hotel room or WiFi café is easier than finding your connecting flight. $35

Light show: The lightweight Solar Puff is a waterproof, pop-up, solar-powered lantern that illuminates everything from camping trips to outdoor soirees. The product is brilliant in more ways than one: The brand behind the magic, Solight—a member at WeWork 123 E 23rd St in New York—is on a mission to provide sustainable light and power to areas of the world that need it most. $30

Sweet dreams: Any jet-setter worth their roller bag knows that the real key to enjoying a vacation is getting some solid shut-eye. The Good Night Sleep Tight Kit from new WeWork member Izola has all the tools to help you drift off: an eye mask, earplugs, bath oil with calming lavender, and a face oil to keep skin dewy, even on long-haul red-eye flights. $35

New flame: The soy-wax candles—based on U.S. states—from Homesick are fragrant reminders of a specific favorite vacation spot, childhood stomping grounds, or college hometown. (The Colorado candle, for instance, smells like spruce needles and spice.) Each uniquely-scented blend is hand-poured in the U.S. $30

For the foodie

Small fry: The 8-inch Chatham ceramic frypan from GreenPan, based at 1460 Broadway in New York, makes even simple morning eggs that much easier thanks to its nontoxic, nonstick finish. It’s dishwasher-safe and can be safely used with metal utensils. Insert prayer-hands emoji here. $40

Buzz feed: Take someone’s morning brew to the next level with Al Mokha Reserve’s Al Wudiyan coffee, which comes ground or in full beans. The medium roast has citrus and cherry notes, but it’s not just a tasty cup of joe; the company, which works out of WeWork Universal North in Washington, D.C., has a sweet mission: to promote economic stability and security in Yemen by creating jobs there. $32

Sugar rush: The Sabiya Gift Box from Elements Truffles is a chocoholic’s nirvana: It includes three chocolate bars, eight assorted truffles, and a bag of turmeric-infused drinking chocolate. Plus, all are Ayurvedainspired—which means they’re technically good for you (right?). $35

Authentic eats: The Classic box from Bokksu, a member at WeWork 205 Hudson, is chock-full of straight-from-Japan treats, such as hand-ground matcha and Hokkaido milk cookies. It’s basically like gifting someone a direct flight to Tokyo, minus the TSA lines and jet lag. $39

Joe on the go: Three busy dads, all members at WeWork 81 Prospect St in Brooklyn, came up with the idea for Stojo, a collapsible silicone coffee cup that’s commuter friendly—and keeps disposable cups from hitting landfills. Drink up. $25

For the fitness enthusiast

Save our strands: Pop the Hair-O-Scopes Brightest Stars set from Brigeo, a member at WeWork 27 E 28 St in New York, in a friend’s gym bag to save them from generic-gym-shampoo disappointment. The kit contains shampoo, conditioning spray, blow-dry cream, and a conditioning mask to help hydrate dry winter hair. $39

Write on: All it takes is five minutes a day for someone to write their way to a more positive outlook, whether that drives them to accomplish new goals in the weight room or finally commit to a half-marathon. The Five Minute Journal from Intelligent Change uses psychology research to help the author focus on gratitude. $23

Clear winner: The sleek A6 bottle from Memobottle, a certified B-Corp company, is designed to be the same size and shape as an A6 memo pad—meaning it slips easily into a pocket or gym bag—making it a stylish reminder to hydrate before and after a workout.  $28

Fitness fixer-upper: You know your cycling-class buddy who always forgets their socks? The Pinch Provisions gym kit is for them. The pocket-size kit also contains earbuds, deodorant towelettes, electrolyte tablets, and more—so they’ll never be caught unprepared again. $24

Toe tappers: After a sock-soaking workout, it’s a joy to change into these Conscious Step Socks That Fight Poverty. The sustainably run company, which works out of WeWork 109 S 5th St in New York, donates to various charities around the globe. Each style benefits a different cause; this particular pair aids Global Citizens, a social-action platform to end poverty. $15

For the Workaholic

Save face: Help your favorite type A unwind with a little self-care. Oars and Alps, a brand started by two members at Chicago’s WeWork 220 N Green St, offers a starter kit of their favorite all-natural picks: face and eye cream, a rollerball eye stick, and mint lip balm. $48

Tag, you’re it: Show your favorite supervisor who’s boss with a keychain and tag that says it all. The hand-stamped brass tag from Art Ayaloka is a constant reminder of their confidence and success. $20

It’s lit: Lighting the Balsam Fir candle from Ranger Station, a member at WeWork 901 Woodland St in Nashville, is like setting yourself down in the middle of a balsam-lined forest and breathing deep. And the calm keeps coming: The candle’s burn time is 40 hours. $44

Fresh start: Help a coworker beat burnout with a Bergamot Bath Bar from Commodity, a member at WeWork 401 Park Ave S in New York. The scent was devised by a scientist with a Ph.D. in chemical engineering, and the blend of citrus and bright green notes is an invigorating way to begin every day. $24,

A good sign: The phrase “What Good Shall I Do This Day?” was a mantra of Founding Father Benjamin Franklin—a man who knew a thing or two about innovation. This enamel steel sign from Best Made is a brain-boosting addition to any workstation. $32