Playdate 11 | Rachel Wolff In Oakland



Hello everyone! Welcome to another playdate!

This time, my friend Rachel Wolff, who is currently looking gorgeous at 36 weeks pregnant, and her 4.5 year old son, Otis, invited us over to their beautiful home in Oakland. Rachel is a merchandsing and brand strategy consultant for many independent and established retail and lifestyle brands. We’ve only met a couple months ago but we instantly connected! Perhaps it was our background in retail, or love for fashion and style, or being a second-time mother… probably all of the above! But whatever it was, it felt like I’ve known her forever!

We had so much fun watching our kids played together. Otis was so welcoming to Hayden and Hadley, and he made them feel like it was their home. What a sweet boy?! I can’t think of a better way to soak in all the sun than hanging out in a nice backyard (one that we envy very much living in our SF apartment!) 

Let’s meet my friend Rachel and her son, Otis, and see how she’s handling her second pregnancy, motherhood and running her own career.


Are you having a boy or a girl? Girl!

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Is the second pregnancy harder or easier? Harder! With Otis I felt amazing the entire pregnancy, this time around we are so excited to be having a little girl, but to be honest I am much more tired! Juggling a preschooler and career makes relaxing during pregnancy more challenging than the first time around! No more sleeping in.

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What drives you to own your own strategic consulting business? How do you keep yourself motivated? My clients and the brands I work with inspire me, they are so talented! I adore working with designers and founders, being able to take their vision and support them with strategy to grow and realize the potential of the brand and often in the process reinvigorate the original mission and voice of the brand. I am obsessed with the brands I work with and love increasing the business, it is super exciting to see sales trend!

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How are you balancing a career, second pregnancy, and a toddler? Do you have help? My mom is a huge help with my son. Having family close by was a huge factor in our move from NY to SF. I love my career; I am really passionate about my work and all of the brands and clients I have partnered with along the way. Otis was the catalyst for my shift into consulting from a career in corporate retail. Initially it was to find more balance and flexibility, but what I discovered is that I love working with smaller brands that I believe in! Consulting is so rewarding and I am able to balance being a mom, being creative, and driving a business.


On me: Colorblock Boyfriend Shirt, White Skimmer Jeans, Gap | Sunglasses in Black, Ray Ban | Purple Sneakers, H&M


You have lovely serveware pieces for entertaining. Where did you get them? The dishes and serving pieces we used are handmade by my mom, Cheryl Wolff. She is a ceramicist here in Northern California. Our home is filled with her dishes, vases and garden sculptures and I love having a piece of her beautiful work in our daily life at the table.

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Snack time involves a nice and healthy spread of fresh fruits, madeleine cookies, Quaker chewy granola bars, and icy-cold lemonade! This simple set-up made the kids so happy and gave them lots of energy to jump around afterwards.


What’s your advice on dressing for pregnancy? I am not the best person to ask, my advice, improvise! I am not big on maternity shopping. I work it out with a collection of oversized dresses mostly Isabel Marant, Organic by John Patrick oversized tanks (Mill Mercantile), A new pair of Birkenstocks to save my pregnancy feet in our recent heat wave. I have picked up a couple other great staples from: Topshop Maternity, Asos Maternity and Hatch Collection. Oh and you have to have at least 1 great pair of maternity jeans! Mine: Jbrand and Asos.


On Otis: Chambray Shirt, Gap | Pants, The Podots

Where do you shop for Otis & your new soon-to-be-born baby?
I really love SF for the focus on sustainability and shopping locally. In NY I always loved Dagmar Daley basics for boys and now that I am out here she keeps my son looking so cute. I love the Podots for kids and the Podolls for me, another amazing locally made in SF brand. Great SF stores? Tug Tug, the closest store I have found to NY, and also Cotton Sheep, they carry Fifth / and a great assortment Japanese kids brands. In NYC I loved Makie. For bigger brands I love Tea Collection, Crewcuts, Zara & lately Gap kids too!


On Hayden & Hadley: Strawberry Boxy TankBubble Shorts, Espadrille Shoes, Gap | White leggings, H&M | Sneakers, Zara

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On Rachel: Vintage Jumpsuit, Loeffler Randall | Back-Button Tank (worn reversed as vest), Ali Golden – Preggo mamas take note – this is so creative – making your current wardrobe work for your pregnancy! | Clogs, No. 6 | Bracelets, Marissa Haskell, SheRise, Julie Nolen

Has your personal style changed since you had Otis? My shoes! I am 5’2” and I used to be high heels 24/7, since having Otis I have embraced flats, clogs and mid-heels and sneakers and honestly don’t know how I wore the heels all day! I love finding shoes that are chic but wearable- like local designer Martha Davis (one of the local brands I work with, re-launching her collection in Spring 15). Her shoes are incredible. I need to be able to scoop him up and head into a meeting, so I try and focus on styles that are chic but not dangerous!

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What does a typical day look for you? Everyday is a little different; this is one of the things I love about consulting. I balance working from my home office and spending days with my clients. Most days are something like this: wake up, my husband always makes me a coffee (currently decaf latte), we try to always eat breakfast as a family before the day gets going. Drop Otis off at preschool. Head to SF for a client meetings, grab coffee or lunch with a friend in SF, finish up the day in my office at home (I get so much more done in my own office!). Pick up Otis, head to the pool or head home to play, dinner and hopefully a family walk if we can swing it. A few nights a week I carve out personal time with a date night with Tim or dinner with friends – I need it! It rejuvenates me! Fridays are my favorite, my day off with Otis.

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How are you prepping Otis for a younger sibling? He is pretty excited, he calls her “his baby” and he actually named her! More details when she is born. But he is also super sensitive and already sharing his feelings about no longer being the center of our universe. To tackle this subject together, we go to the library and check out stacks of books about being a big brother and changes in a growing family. He loves to read them and ask questions, especially about the funny stuff like wearing a diaper! We are also planning our special mom and Otis time, a weekly date night for the just two of us when the baby comes, right now he really wants to make this pizza and ice cream night. So many amazing new restaurants in Oakland so should be fun for both of us!


Brooklyn or Oakland? Both! Everyone is obsessed with the Brooklyn / Oakland parallels these days, for me, Brooklyn is the best but so is Oakland and our lifestyle here is unparalleled: great weather, amazing food, a big sunny backyard, family close by, crazy natural beauty, and creative people doing inspiring stuff everywhere. The one thing I really miss ? Walking everywhere and the shopping. SF/ Oakland is getting there, but we still don’t have NYC / Brooklyn options. I do love being in a place that is changing- Oakland is getting more awesome every day, we moved here at a great time!

Thank you so much to Rachel and Otis for inviting us to their beautiful home! And many thanks to Ashley Batz for another great Playdate shoot! 

This post is kindly sponsored by Quaker, serving up wholesome goodness in delicious ways. Quaker Chewy helps give kids the energy they need to play. That’s why Quaker and NERF are teaming up to fuel backyard fun, helping families get out and get active together, right in their own backyard. When you buy three specially-marked boxes of Quaker Chewy, you can enter the codes online to get a free Nerf sports item!

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All opinions shared here are my own. Many thanks for supporting my sponsor and my playdate series!

xo Jeanne