Jenna Lyons On How To Be Truly Happy, RHONY, Career Advice, Dating, Sex, & How To Be Yourself

By | October 31, 2024

#630: Today, we’re sitting down with Jenna Lyons. You may know her from Real Housewives of New York City, but Lyons rose to fame in the early 2010s as the lead designer for J.Crew; her work at the time popularized the concept of ‘high-low dressing’ and earned her the title of the ‘Woman Who Dresses America’ due to the massive success of her campaign to reinvigorate the then-struggling brand. Today, we sit down with Jenna to discuss topics ranging from childhood and how to build resilience to her experience on RHONYC and how that’s shaped the way she sets boundaries. She also gets into career development, dating advice, and what men can do in their relationships to keep the spark alive. 

To connect with Jenna Lyons click HERE

To connect with Lauryn Evarts Bosstick click HERE

To connect with Michael Bosstick click HERE

Read More on The Skinny Confidential HERE

To subscribe to our YouTube Page click HERE

For Detailed Show Notes visit TSCPODCAST.COM

To Call the Him & Her Hotline call: 1-833-SKINNYS (754-6697)

This episode is brought to you by The Skinny Confidential. Click HERE to shop the last day of our Cyber Monday sale.

This episode is brought to you by Alo Moves

Alo Moves has always been inspired by a single goal: to empower people to live healthier, more fulfilled lives. Alo Moves is the streaming on-demand platform with yoga, fitness, and meditation classes. Go to Alomoves.com and get 1 year of Alo Moves for only $99 with code SKINNY99 at checkout.

This episode is brought to you by Quince

Get affordable luxury with Quince. Go to Quince.com/skinny to get free shipping and 365-day returns on your next order.

This episode is brought to you by Just Thrive

These days, stress seems to hit us from every possible angle in any environment at any time, day after day. Enter Just Calm – the breakthrough new stress and mood support formula from Just Thrive. Get 20% off a bottle of Just Thrive probiotic + Just Calm supplement at justthrivehealth.com or use code SKINNY90 at checkout.

This episode is brought to you by Canopy

Canopy just released a new filtered shower head that greatly reduces contaminants and odor in your water, leaving you with glowing hair and skin. Visit getcanopy.co and use code SKINNY for an additional 10% off your purchase.

This episode is brought to you by WeightWatchers

WeightWatchers is the #1 doctor recommended weight-management program and the trusted authority in evidence-based weight-health. Visit ww.com/tsc to see if you qualify, and if you do, use code TSC25 to get one free month plus $25 off your second month.

This episode is brought to you by L’Oreal

Discover the new Bright Reveal Dark Spot Duo! Visit Target online and in-store to buy yours today.

Produced by Dear Media

Editorial Stories
Why Is It So Quiet in the Taylor Swift and Travis Kelce Camp? Sources Say They’re at a ‘Turning Point’
Why Is It So Quiet in the Taylor Swift and Travis Kelce Camp? Sources Say They’re at a ‘Turning Point’
A Look Back at Sharon Osbourne’s Legendary Career As Ozzy Retires from Black Sabbath
A Look Back at Sharon Osbourne’s Legendary Career As Ozzy Retires from Black Sabbath
Beauty Influencer Golloria George Says She Won’t Compromise Her Commitment to Inclusion
Beauty Influencer Golloria George Says She Won’t Compromise Her Commitment to Inclusion
Trending Products
Feel Good Trucker – White Feel Good Trucker – White
NEW
Feel Good Trucker – White

$32.00
Feel Good Trucker – Navy Feel Good Trucker – Navy
NEW
Feel Good Trucker – Navy

$32.00
Related Articles
Our Shows
Over 50 & Flourishing
Welcome to Over 50 & Flourishing, the show for any woman who feels like she lost her compass in the sea of midlife. I’m here to tell you it’s never too late to change your course and awaken the healthy, wise, and wonderful woman within. My name is Dominique Sachse, and I love to ask questions, which was why I spent nearly three decades of my life in the TV news business. I also started a YouTube channel in 2014 to connect intimately with my community, and I took an even deeper dive in my book Life Makeover - Embrace The Bold, Beautiful and Blessed You. I’ll be the first to say, I’ve made mistakes, and I’m not afraid to be vulnerable and learn from them. I mean let’s face it, this stage of life can be complicated. Children are moving out, relationships are being examined, our parents are aging, and we’re having to manage all of this along with our menopause! It’s easy to lose sight of ourselves, but can I just say.. we matter. So, whether it’s finding ways to enhance and celebrate our own beauty, taking bold steps toward living our best life in the second half of life, finding ways to be healthier, happier, and more spiritually connected, I will bring you thinkers and innovators who share the same passion of flushing out these ideas. It’s my goal to leave us all feeling inspired, thought and intent-driven, and with a sense of purpose in whatever we pursue. Let’s celebrate growing older together and embrace our Prime. It’s our time!
Over 50 & Flourishing

Dominique Sachse
Give It To Me Straight
Follow along as this husband and wife duo give you unfiltered advice from two different perspectives. No topic goes unspoken, from sex, money, relationships, the good the bad, and the ugly. Alex and Jon will give it to you straight.
Give It To Me Straight

Alexandra Madison & Jon Bouffard
After Bedtime with Big Little Feelings
Real talk? Modern parenting is a doozy. There’s never been more pressure to be perfect with social media readily at our fingertips - mixed with total isolation and no help. Where the f*ck is that village everyone talks about? Consider After Bedtime your village. Led by Kristin and Deena - founders of the largest online parenting community, Big Little Feelings - After Bedtime is the place you can go at the end of a long hard day to find your “enough”-ness. We’ll laugh, we’ll cry, we’ll maybe pee our pants a little as we unpack things we’re ALL experiencing but too ashamed to talk about: imperfect marriages, miscarriages, managing toddler mania, apologizing to our kids and everything in between. You’ll leave with actionable, realistic tips to make this whole parenting thing smoother - small changes, big impact. In an age where parents need more *real* connection than ever, let’s talk honestly about the hard - and remind ourselves we are not alone, we are not failing. In fact, we’re f*cking crushing it.
After Bedtime with Big Little Feelings

Deena Margolin & Kristin Gallant
Everybody’s Crazy
If you’ve been outside recently, you know that Everybody’s Crazy. Whether you’ve got a story to share, or want guidance on how to navigate your crazy situation, hosts April McDaniel and Savannah James are here to answer your call-ins, lend their feedback, and share a little of their crazy too.
Everybody’s Crazy

Savannah James & April McDaniel
Better Half
From 9 to 5, one’s the boss; from 5 to 9, the other calls the shots. Together, Anastasia Karanikolaou – aka Stassiebaby – and Alexis Fisher create the perfect balance. Better Half is your backstage pass into the world of friendships, relationships, and the entertainment industry—where personal meets professional and chaos is part of the charm. They say opposites attract—these two are a beautifully unhinged recipe for something you won’t want to miss.
Better Half

Stassie Karanikolaou & Alexis Fisher
The Intersect
The Intersect is a new show about how technology, media, and culture are not just shaping our world—but more than ever, reconstructing our realities in real time. Join Cory Corrine, multiple Pulitzer Prize-winning journalist and media executive, in exploring the connections in the systems that are making us, in critical conversation with the people imagining what comes next.
The Intersect

Cory Corrine
No Guide For This
No Guide For This is a refreshing new podcast from Dear Media and The Bump that explores the uncharted territory between adulting and becoming a parent. Hosted by Jen Hayes Lee and Sasha Smith, this podcast taps into the heart of the transition from managing life as a grown-up to navigating the unpredictable world of parenting. Featuring insightful conversations with celebrity guests, the show blends humor, honesty, and relatable stories, giving listeners a sense of community during this pivotal life stage. Whether you're debating if you want kids at all or managing the juggle of multiple little ones, "No Guide For This" provides a candid look into how life, relationships, and identity shift when children enter the picture.
No Guide For This

Jen Hayes Lee and Sasha Smith
Live From Bed
Live From Bed is your official invitation to hide from the world with me — your permission slip to unravel out loud. Every Wednesday, I pull the covers over my head and drag my favorite people in with me — from internet sensations to experts — to celebrate our bad habits, worst traits, and the internal monologues that probably make both our therapists and the group chat nervous. We talk about the friendships that downgraded from ride-or-die to ‘hope you're well’, the plans we’re praying get canceled, the milestones we’re nowhere near — and the texts we wish we hadn’t sent. If your best friend’s ignoring your FaceTime… and you’ve already messed up one too many social interactions this week, this is your place. No unsolicited advice. No annoying success stories. Just the things we all think but wish someone else would say first — and a whole lot of commiserating.
Live From Bed

Jade Iovine
Come Together
Time to cut the cameras and turn ON the mic — Erin and Abe Lichy are pulling back the curtain on the wild ride of marriage, sex, business, and everything in between in Come Together. As a powerhouse couple who’ve built empires together—Erin as a serial entrepreneur, interior designer, and Real Housewives of New York star, and Abe as a sharp legal mind and founder of The Advisory—they’re the couple you want at your dinner party, the ones you want to grab a drink with, and the first ones you’ll turn to for advice. Each week, the duo will dive into the real, raw, and often unspoken realities of blending parenting, business, and love — all while keeping it real. With their signature honesty, wit, and easygoing vibe, they’re baring it all. Whether they’re talking business wins, how to keep the spark alive after nearly 15 years, or just the chaos of everyday life, no topic is off-limits. Tune in every Monday for the real secret behind what it really takes to Come Together.
Come Together

Erin and Abe Lichy
The Pre-Game with Kayla Nicole
Everyone knows the best part of any night out is the pre-game. You know the vibes – feels like a hype session in the bathroom mirror. From group chat debriefs to deep dives into the latest headlines (with a drink in hand, of course). The Pre-Game with Kayla Nicole is exactly that: the party before the party. Each week, we’re diving into all the things you and your homegirls actually talk about, from pop culture tea and beauty secrets to those ‘what would you do?’ scenarios that have you screaming at your phone. It’s unfiltered, hilarious, and has just the right amount of chaos, served with a splash of tequila and zero apologies. So grab your gloss, pour up, and let’s pre-game.
The Pre-Game with Kayla Nicole

Kayla Nicole
Audio thumbnail
How To Harness The Power Of Your Sexuality ft. GG Magree
00:00 / 49:29
Link copied to the clipboard!