Podcast Summary: Laugh Lines with Kim & Penn Holderness
Episode: Wearing What You Want with Stacy London
Date: August 19, 2025
Host(s): Kim & Penn Holderness
Guest: Stacy London
Episode Overview
This lively and heartfelt episode of Laugh Lines dives into aging, identity, and style with the iconic Stacy London. Kim and Penn discuss how fashion and self-expression shift with age—particularly through perimenopause and the midlife era. Stacy London brings her signature humor, expertise, and candor to a conversation brimming with insight for Gen Xers, parents, and anyone who’s ever felt lost in a department store. The hosts and Stacy tackle cultural, generational, and personal shifts in style, all while emphasizing joy and self-acceptance.
Key Discussion Points & Insights
1. Changing Relationship with Fashion as We Age
- Body shifts and confidence: Kim opens up about her evolving body and confusion about what to wear in midlife.
- Kim: “Items have shifted during flight right now...I don’t know how much I care, but B, I will walk in the store and...I don’t know. What I don’t know.” (13:12)
- Fashion as self-care and joy: They reflect on how looking good can change how you feel, not for others’ approval but for self-esteem.
- Kim: “I’m not dressing for you…I’m dressing to feel good about myself.” (06:39)
- Gen X and the Uniform Phenomenon:
- Quarter-zip sweaters as the “Gen X dad thumbprint” and the yoga pants/athleisure trend for moms.
2. Stacy’s Perspective: Midlife, Menopause & Identity
- Rejecting ‘expiration dates’:
- Stacy: “You don’t have an expiration date for being powerful, capable, hot, any of the things you want to be. It’s the values you held in your youth that have an expiration date.” (10:12)
- The evolution from ‘rules’ to individuality in fashion:
- Stacy describes why she was reluctant to return to a makeover format and how her philosophy has shifted from giving rules (What Not to Wear era) to empowering self-expression and agency in her new show, “Wear Whatever the F You Want.”
- Stacy: “We originated the rules and now we’ve got to show people how to break them.” (11:15)
3. Generational Differences & The Store Experience
- Gen X vs. Gen Z and Millennials:
- Gen Xers and Boomers crave rules; younger people are more creative and body/gender-positive in fashion.
- Stacy: “Our generation, Generation X, we’re all about rules…young generations are so much more open. Open. There’s so much more body positivity, so much more gender positivity...” (13:22)
- Store overwhelm is real: Even Stacy notes the confusion of in-store shopping with body and cultural shifts.
4. COVID-19’s Impact on Style and Comfort
- Permanent changes post-pandemic:
- Athleisure, “pajamafication,” and the decline of high heels as style expectations relax.
- Stacy: “I don’t think anybody wants to wear hard pants again…we have a very different perspective on our work life, our personal life, our priorities.” (20:59)
- Kim: “I loved shoes and I loved my heels. I don’t think I put on a pair of heels to go to a wedding. ...I am in sneakers all the time. I am in the baggy jeans.” (23:32)
5. Practical Midlife Style Tips from Stacy
- Building a wearable, joyful wardrobe:
- Shop in outfits, not just one-off pieces.
- Use a “grocery list” for missing basics in your closet to avoid mindless shopping.
- Prioritize clothing that has “use, value, and joy.”
- Don’t fear tailoring—alter pieces so they fit and flatter.
- Stacy: “My two criteria for wearing anything are use, value and joy...and then I also recommend shopping in outfits instead of just a one-off piece because a lot of times we come back and we think we found something brilliant and we can’t figure out what to wear with it.” (25:44)
- On breaking out of color ruts:
- Kim admits to buying endless black and white—Stacy suggests editing down and being intentional about branching out.
- Stacy: “It’s about stretching yourself in your closet and figuring out what you can get rid of, because if you have that many of the same thing, you are not wearing all of them.” (43:53)
- Donate or swap excess clothes instead of throwing them away.
6. Fashion & Gender—The Male Perspective
- Penn’s “uniform” and male insecurity:
- Men tend to buy multiples of what works and are hesitant to try new styles/colors.
- Stacy notes straight men (especially Gen X and up) often hide their investment in appearance.
- Stacy: “We all care about the way that we look. Men, women, whatever gender you are…because that’s how we get accepted. That’s just sociobiology.” (32:32)
- Encouragement to experiment:
- Stacy: “If you want to do something different, then the first place I would start with a man is color.” (33:48)
7. Is “Age Appropriate” Fashion a Thing?
- Stacy’s take:
- Not really—dress so you feel powerful and happy, not to appease others or age standards.
- Give (and graciously receive) compliments; kindness is powerful.
8. The Inside Story: Body Image in Fashion Media
- Stacy opens up about her time at Vogue:
- She felt out of place and responded by being the “class clown” and working thrice as hard.
- Stacy: “The fashion industry is built on insecurity. It doesn’t run on money. It runs on insecurity...what if we came at fashion from the opposite perspective? See, fashion is an industry, but style is for the individual.” (49:15)
- Empathy and kindness to self:
- Stacy: “If I can do that, then I can walk through the world with a certain amount of self assurance. Doesn’t mean I don’t have insecurities, but I’m not going to let insecurity run my life.” (51:04)
9. Social Media & Self Esteem
- Guardrails and compassion:
- The unintended negative consequences of social media are discussed. Confidence, not consumerism, should be fostered.
- Stacy: “…a lot of the outcomes of social media were possible, but we didn’t think they were probable…all the other things (isolation, comparison, envy) have not been great…Any great stylist will never impose their style on you. They will find the style that lives in you.” (51:14)
Notable Quotes & Memorable Moments
- Stacy on midlife power:
- “It’s not that you have an expiration date…It’s the values that you held in your youth that have an expiration date.” (10:12)
- Stacy on fashion rules:
- “We originated the rules and now we’ve got to show people how to break them.” (11:15)
- Stacy on the power of clothing:
- “It gives you the power to get people to think what you want them to think about you.” (38:06)
- On male fashion vulnerability:
- Penn: “I believe that men are more vulnerable than they let on when it comes to fashion and aren’t really wanting to stem out on anything new.”
- Stacy: “I agree with that…and certainly for our generation, there is some kind of weird…you don’t want anybody to know that you care. Right? But we all care.”
- On body image in the industry:
- “I was knocked. I had gone through a college eating disorder…I got sick…And my way of dealing with that was by being the class clown, by working three times harder…The fashion industry is built on insecurity.” (48:08)
- Ode to Stacy (Penn’s Song):
- “She used to be a makeover juggernaut. Now she says wear whatever the F you want.” (64:54)
Timestamps for Key Segments
- Intro banter & trend talk: 02:55–08:03
- Stacy London joins the show: 08:35
- Role of menopause & midlife in fashion: 09:20–11:15
- Evolution from “What Not to Wear” to “Wear Whatever the F You Want”: 11:15
- How to shop at midlife, practical tips: 24:21–31:40
- Cluttered closets & color ruts: 43:21–45:21
- Body image, fashion magazines, and industry secrets: 47:43–51:04
- Compliments, confidence, and age-appropriateness: 46:18–47:43
- Social media and confidence: 51:14
- “Ode to Stacy” original song: 64:04–65:41
Stacy’s Projects & Final Thoughts
- Wear Whatever the F You Want on Amazon Prime—a show about breaking fashion rules and embracing midlife style.
- QVC clothing line by Stacy London—designed for comfort and relevance, especially for the 40–60+ age group.
- Amazon storefront with Stacy’s personally curated favorite items.
- On thriving in middle age:
- “I think that middle age…is really an amount of time where you go from a real reckoning to a renaissance. And… the most important thing is identity. ...There is a light at the end of the tunnel.” (59:00)
Episode Tone & Takeaways
Uplifting, frank, and genuinely funny, this episode blends real talk about body image, aging, and cultural change with practical, actionable tips and plenty of comic relief. Stacy’s presence is empowering, and Kim and Penn bring warmth and vulnerability. If you’ve ever felt confused by changing trends, lost in your own closet, or unsure how to dress your ever-evolving self, this episode offers camaraderie, affirmation, and a healthy dose of “wear whatever the F you want.”