What I Wear to Work (at Home): Olivia Landau, Founder and CEO of The Clear Cut

She tops off her WFH look with diamonds.

what i wear to work olivia landau of the clear cut
(Image credit: Courtesy)

In a bi-weekly series, we're interviewing female executives, founders, CEOs—basically, boss ladies—on their "power suit" a.k.a. the outfit they wear every day for easy dressing to conquer whatever the job throws at them.

Couples thinking about popping that question, will want Olivia Landau's insight. She's the founder and CEO of The Clear Cut, an engagement ring company she runs with her husband and co-founder Kyle Simon (also COO). The two launched The Clear Cut in 2017 after it was clear (pun intended) that not only were their friends interested in Landau's engagement ring advice but also strangers who were DM-ing her Instagram.

"I started The Clear Cut as an educational blog because I realized most people didn't know the first thing about buying an engagement ring," says Landau. "The blog never had a wide scale audience, but then I started posting some ring designs on Instagram and I started getting design requests. I was working [my full-time job] while running back and forth in the diamond district [in NYC] for this little side hustle."

the clear cut

"Tons of couples work together to pick out the diamond and design the ring. I've also seen that some women want to financially contribute to the ring."

(Image credit: Courtesy)

It wasn't long before this side hustle became a real business; Landau and Simon were primed to start their own thing. Landau comes from four generations of diamond cutters and dealers and is a Gemological Institute of America (GIA) graduate. Simon, meanwhile, started a diamond mining company in 2013 and is a graduate of both Columbia Business School and the GIA. (Fun fact: The couple first met while taking courses at GIA!)

For anyone thinking of following in Landau's footsteps, she reveals that breaking into the diamond industry without any connections is difficult. The community is tight knit and there is a lot of trust involved. "This field is mostly dominated by middle aged or older men, so it's quite challenging if you are a younger woman and one who maybe doesn't have ties in the industry," she says. "I think what really helped me was going to GIA and building a network and connections there. Also, working in so many different facets of the industry, from retail to wholesale, and meeting people along the way really gave me a good understanding of how the business worked before actually doing it myself."

the clear cut

Landau hosts weekly Q&As about engagement rings on Instagram.

(Image credit: Instagram user theclearcut)

Being a young woman in this sector can have its advantages, though. For one, Landau is social media savvy (she runs The Clear Cut's Instagram account). She has a friendly appearance to millennial ring shoppers. Her transparent Instagram posts have helped demystify the convoluted engagement ring process. In addition, about 80 percent of The Clear Cut's clients are remote, which means Landau has devised a strong and flexible system for reaching customers beyond New York City, where the jewelry is made.

"When I was at GIA, I remember one professor saying there's no way people would ever buy diamonds online without first seeing them in person, but we've seen a dramatic shift [on that thinking]. I think our generation and the next are comfortable buying online, so there's less friction when [virtually] ring shopping," she says. "The customers today are very interested in what they see online. Everyone wants exactly what they want. They don't want to buy something cookie cutter."

Landau and Simon lead a team of seven in NYC and work with a few hundred customers at a time, helping them source the perfect diamond to create their dream engagement ring. Inquiries dropped in the first month or so after the COVID-19 pandemic hit, but are now picking back up.

"A lot of our master jewelers aren't able to come into work and we had a bit of delay in production, but we were able to figure out how they can work from home," Landau says. "Also, since most of our our clients are remote, we've been really leaning into that and I'm doing a lot of things that I wasn't doing before, like going into the office and shipping out packages because I can't risk the safety of our staff." (Landau lives just a 15-minute walk away from the work place.)

Ahead, The Clear Cut founder shares how her day-to-day routine has changed since the health crisis and what she wears for work now that she's mainly WFH.

Her Morning Routine

"My morning routine has changed so much. It used to be that I would get ready the last second I possibly could and rush to brush my teeth, wash my face, put on makeup, drink coffee, and run out the door. Now, my mornings feel more leisurely. I wake up, make some eggs, and drink my lemon water/coffee—this is the first time I'm eating [a real] breakfast. Then I'll answer emails, hop on some phone calls, figure out my day, and maybe go into the office. We're really lucky that we work close to our office because I can easily pop in to pack some shipments, drop them off at the post office, then head back home."

the clear cut olivia landau

Lately, Landau often chooses athleisure wear.

(Image credit: Courtesy)

Her Getting Dressed Strategy

"I'm more of a wake-up-and-throw-on person, but I do [get dressed] based on what I'm doing that day. If I know it's a Q&A for our Instagram that day or I'm filming something, then I'll put on a cute top with my workout pants because I know people will see me. Most of the time, if I'm just going to walk outside, I'll wear my sneakers and athleisure attire. I have my pajamas that I sleep in and then my comfy day clothes because even dressing up slightly motivates me more."

Her Work Uniform

"Since I'm not meeting with clients one-on-one anymore, I have been more relaxed in my everyday dressing. I don't think I've worn real pants since this pandemic happened, so I'm living in loungewear and cute workout gear all day, every day. I've been wearing a lot of different types of leggings from labels such as Outdoor Voices, Athleta, and Terez, which has a bunch of really cute, fun printed leggings.

Also, I love comfy sweatshirts or tops that I can throw over a sports bra. There's this cute little sweat suit with stars I have from Terez, and I also wear my Alexander Wang hoodie all the time. I try to still dress kind of cute and match, but my work outfits definitely have more of a casual vibe to them now. For shoes, I like classic white Adidas, and if it's a nice day or I want to be a bit more funky, I'll wear Allbirds. I also have a few pairs of classic Nike sneakers, like the white Air Force 1, which makes any outfit look better.

the clear cut

The Clear Cut sells fine jewelry in addition to engagement rings.

(Image credit: Courtesy)

I've still been wearing a lot of jewelry—I love layering pendant necklaces with a piece like joggers. I just switched to stud earrings and I'm trying to wear jewelry that I can easily layer on and not take off when I'm working out or running errands. This makes me feel like I'm still accessorizing and really elevating my outfit."

The Three Words That Describe Her Power Outfit

"Comfy, cute, and something that I can feel like confident and comfortable in."

Her Motto

"Don't wish for it, work for it. I'm a firm believer in doing what I can to achieve whatever goals I have in mind."

Get Landau's athleisure-chic WFH look, below, by shopping her favorite brands:

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Marina Liao
Fashion Editor

Marina Liao is the former fashion news editor at MarieClaire.com, where she covered celebrity style (from Meghan Markle to Katie Holmes), fashion trends, and shopping advice, plus conducted original interviews with industry insiders. She's also had many opportunities to write content in other areas such as beauty, food, tech, and even home. Her previous fashion stints include POPSUGAR and Cosmopolitan.