Preppy Hippie Mom on the Street: Tessa Duquette

Tessa Duquette of OBoy Creative has an eclectic taste when it comes to style best described as “preppy hippie“. She mixes in vintage pieces handed down to her from her grandmothers, skinny jeans, and ADIDAS sneakers so she can chase after her kids!

Here are some of her best preppy hippie style secrets:

Preppy Hippie Style

Which three words best describe your style?

What are your favorite places to shop for your preppy hippie look?
Give me an hour in TJ Maxx by myself and I’m golden! I like J Crew‘s button-up shirts – they fit fantastic. I found a bunch of cool blazers at a thrift shop in Norfolk a few months ago and cannot wait to wear them more often as the weather at the beach begins to cool down.

Helene Burton

Who’s your favorite style icon?
A famous style icon would definitely be Audrey Hepburn. But I had my very own style icon growing up: my grandmother, Helene Burton. She had the best style and taste and was always dressed to the nines, no matter the occasion big or small. My grandmother grew up in Philadelphia but spent most of her life on the Eastern Shore of Maryland, and in Rehoboth Beach, DE. In her early twenties, she designed her own clothes and had a seamstress create these stunning outfits for her. She passed along many of her collections which range from Lilly Pulitzer to vintage purses that I cherish, and wear or use.

What’s your best style advice? Make sure your clothes fit you correctly. I struggled with this especially after having three kids. Wearing clothes that fit your body type, make you feel good about yourself, and are comfortable is key! Also, invest in a few key pieces that never go out of style!

Which article of clothing/accessory would you not want to live without? Right now it’s my black jeans. I have a few pairs – and they go with everything! I also wear a “Cape Cod Bracelet” that I haven’t taken off my wrist in many years. I’ve also carried my trusty 76th Street Tote from North End Bag Co for over three years now. When I had my third son, I wanted a hip diaper bag and settled on this handmade bag. It goes everywhere with me! It’s well worn, and so loved. If you dump it over, a pound of sand will probably fall out of all the pockets.

What fashion/style did you love at the time, but now cringe when you see old photos?
Oh gosh – those early twenties outfits that I wore – tube tops and low rise jeans. I remember my mother would always be pulling up my pants or pulling my shirt down. So embarrassing! Yet I thought I looked so cool.

What’s your best preppy hippie style secret? I think I’ve just recently started feeling comfortable in my style. And I think it’s mainly due to the fact of having stylish friends who have great taste and are so encouraging in me finding my own. And once I realized that my clothes needed to actually FIT correctly, then things got a lot easier. Style Erin helped fine-tune my style this past winter, and we put together pieces from my closet, as well as a few staple items that never go out of style.

Stilettos or flats? Flats – I’ve been searching for just the right pair of loafers for the Fall, and just couldn’t commit to the perfect pair. I did, however, find a fantastic pair of slide-on-flats recently from Fabre in the ViBe Creative District, they’re comfortable, trendy, and I can look put together at preschool drop-off as well as in my meetings with clients throughout the day.

Preppy Hippie Family

What’s your favorite way to spend time with your family?
During the summer you can usually find me at the beach or on a bike ride along the boardwalk with my husband and boys. During fall you can find us cheering on my husband’s tennis team, as the kids play around the courts. And once a week, my in-laws host “Salmon Sundays”.

The kids look forward to it every week as well. My father-in-law is a grill master, and the menu is usually “surf and turf”, with a big salad full of Neighborhood Harvest greens. His famous sweet potatoes are always perfectly cooked. The dinner guests are usually a few close friends coaches/teachers from school, who the kids absolutely adore. We sit around their big kitchen counter and dig in, it’s a great time to reconnect with each other over a great meal.

What’s been your best family vacation? We travel up north during the summer to visit my parents in Vermont. Along the way this year, we stopped in the Hamptons for the first time, and stayed with our family friends in their historic house in East Hampton. It was such a magical place! We explored every inch of the Hamptons, and visited 7 different beaches. The visit happened to fall on my 36th birthday, and I spent that day wandering down Main Street drooling over all the fantastic shops and fashion. The Hamptons certainly have style! The Ralph Lauren shop was my absolute favorite, now I just need my own yacht so I have some place to wear their clothes!

Recently, we just returned from an amazing weekend visiting extended family on the Eastern Shore of Maryland. We spent hours on the farm catching up as the kids played. It’s so nice to be able to unplug and reconnect with those around you. R&R is much needed!

Best parenting advice: “You do what’s right for your family”. As a new mom, a friend said this quote to me – and it has resonated ever since. You’re probably never going to do what other people think you “should” be doing (especially regarding those hot parenting topics), so just do what is right for YOUR family.  I also repeat to myself “This too shall pass” on a daily basis. Knowing that whatever you’re dealing with kid-wise at that moment, that it won’t last forever.

Family Meals

What’s your go-to family dinner?I love to cook – and am a big fan of a huge tray of roasted veggies, every color of the rainbow. Fresh pesto noodles, and pork loin cooked in a cast iron with fried onions. I make a mean lasagna as well. About 95% of the time my meals turn out well – I once over seasoned chili and my family hasn’t forgiven me since or eaten my chili either!

What’s your favorite family restaurant?
I like going to restaurants where my kids will eat! Top 5 currently are Moe’s, The Beach Bully, Zero’s Subs, Pelon’s & Whole Foods. If it’s a date night, you can find my husband and me at Esoteric’s bar, sharing a cocktail and eating their delicious chicken sandwiches.

Preppy Hippie Life

What’s your favorite show to binge-watch? I grew up on a farm in Vermont, with no tv (thanks mom & dad!). So I must admit that watching tv is a guilty pleasure for me – and I probably won’t ever grow tired of it. I love crime shows to cheesy romantic comedies. Since there isn’t a whole lot of time to watch tv these days (because well, sleep is important), I tend to fast forward through a bunch of shows to get caught up… Sounds a little nuts but it works.

Watching the show Coach never gets old, my grandmother used to record the episodes on VHS and mail them to us (as well as Bewitched and I Dream of Jeannie). I’ve been a fan of NCIS from the very beginning. Currently waiting for The Marvelous Mrs. Maizel Season 2 to come onto Amazon Prime so I can binge watch that.

What’s your favorite beach read?
I’ll let you know in about 10 years when I’m able to start reading on the beach again.

What’s the best song to dance to when nobody’s watching?
Anything with a beat! I love to dance, having spent my childhood in tap, jazz and ballet classes, and taught Zumba & Barre Fitness classes in recent years. You can often find us dancing in the kitchen. One of my favorite songs is “Good Day” by Nappy Roots.

Preppy Hippie Travel and Shopping

If you could go shopping with anyone from history, living or deceased, who would it be?
My Grandma Betty would take us shopping whenever she’d visit. This is where I get my love of shopping from (especially at TJ Maxx, her favorite store). She would be so patient as we picked out various items, and always so encouraging. I can’t imagine what she thought of my choices in my awkward teenage years! I would want to have one more time shopping with her.

What’s at the top of your travel bucket list?
Europe, Greece, Peru, a rainforest someplace. I own a very heavy book about all the art in the world you need to see before you die… so basically all the places in the book are on my list too. I want to drive cross country one day with my family – I haven’t visited many of the State/National Parks in the United States, so this is a must-do one day!

What’s your favorite way to unwind at the end of a long day?
I like the silence in the house after everyone is asleep. Having the time to reflect on the day, do a bit of work or painting in my home office, and fast-forwarded through a few tv shows. I often catch myself staying up too late just to have that time to myself before it all starts again tomorrow. 

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