What to Wear (and Eat) This Week with Samantha Wasser of by Chloe

What do you ask yourself when getting dressed in the morning

In today’s edition of What to Wear This Week, Samantha Wasser, Creative Director & Partner of ESquared Hospitality and partner of by CHLOE, breaks down the mechanics of what she wears and why.

What’s the first thing you think about when you’re getting dressed in the morning? Explain the process of picking out an outfit in the morning.

Probably my schedule for that day. If I’m running around to meetings all day I’ll try to wear something more comfortable, if I have an interview or a photoshoot I’ll make sure to pay more attention to my outfit and accessories. I’m not such a morning person, so I try to think of a loose idea of what I want to wear the night before. That way I can be out the door as quickly as possible.

What’s the one garment that never lets you down?

A plain white t-shirt. I love Everlane shirts. You can dress it up or dress it down, and always feel comfortable.

Same question, but for food — what’s the one type of nourishment that never lets you down?

Smoothies. I start every day with a green smoothie. It goes with me everywhere!

How about the food that always lets you down?

As a kid I was the pickiest eater, but now I’m discovering that I love a lot of the foods that used to make me squirm. So, to answer your question– not a lot these days!

What do you think about first: clothes or breakfast?

Definitely clothes.

How do you see food and fashion intersecting?

They are both constantly evolving – and while trends come and go, there are always going to be classics you can rely on. Whether its your favorite pizza joint or your favorite pair of jeans.

Fail proof styling trick?

Lipstick can make any outfit look polished.

Best advice you’ve ever received in relation to running a business?

Never be afraid to fail, and most importantly trust your instincts.

How about for getting dressed?

Same advice! Trust your instincts. It’s all about personal style.

Hardest part about the restaurant business?

It’s a 24/7 job. I’m always thinking about the little details and what can be better. Your goal every day is to make the customer happy and have them come back – and that takes work every single day.

Best part?

Seeing how happy our customers are when they get their order and take their first bite and seeing repeat customers who sometimes come in 2-3 times a week! There’s nothing better than seeing people enjoy what we’ve worked so hard to create!

How important do you believe the Instagrammability of a dining space to be?

These days its absolutely imperative! When we were designing the space we thought of the table tops, the lighting, the colors, and then when we started testing the menu, we thought of everything from packaging to how the food was presented, all in relation to how it would photograph. Now, we see customers going all out, standing on chairs to get the right pic.

And the instagrammability of an outfit?

It’s important, but I like to stay IRL when I’m thinking about what I want to wear.

Follow Samantha @itsmesamwass and by CHLOE @bychefchloe on Instagram. Visit by CHLOE’s website and peek the menu (yummmmm). Photographed by Krista Anna Lewis.


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  • Alex

    Love this! You guys should be on Springpop, it’s my new favorite app!

  • Stephanie

    Love this post so much. It’s such an inspiring blog post


  • the SHIRT in 1-3

  • Amelia Diamond

    She makes me want those Trademark shoes in blue now AND THAT BY CHLOE COOKIE MY FAVORITE COOKIE IN THE WORLD

  • lily

    Honestly i am such a by Chloe fan girl. The guac burger is life.

  • svetlana

    instincts and no pizza is my devise

  • Harling Ross

    I want all the clothes and all the food. Still working on that whole “gluttony” sin thing but like CAN I LIVE???

  • kforkarli

    What a gorgeous outfit! Samantha you look so happy!

    • kforkarli

      Okay I’d only clicked through to the 3rd slide – I’m easily won over!