Let's Get Dressed

Getting dressed isn’t just about clothes, it’s emotional, it’s personal, and it’s one of the most powerful tools we have to step into who we want to be. So how do we actually use it?I’m joined by Erin Walsh, the stylist behind some of the most iconic women in Hollywood, Anne Hathaway, Selena Gomez, Mindy Kaling, and the mind behind Anne’s unforgettable Devil Wears Prada 2 press tour.Fresh off last night’s New York premiere, Erin walks us through what it actually takes to build a press tour of this scale, the Easter eggs, the Valentino Rockstud comeback, the meta moments, and why every look comes back to one question: how do you want to feel?We also get into Erin’s CREATE method from her upcoming book The Art of Intention, and how the same tools she uses on red carpets can transform how any of us get dressed every single day.In this episode, we get into:What “intentional dressing” really means and how to actually do itThe 3-word rule Erin uses with every clientHow to find your style “superpower” and lean into itWhy clothes are emotional, and what to do when your closet feels like a strangerHow to get out of a style rutInside the Devil Wears Prada 2 press tour: the references, the collaborations, the chaosThe Valentino Rockstud comeback and why it actually worksHow Erin handles real-time criticism on the biggest carpets in the worldWhy fashion is moving back toward joy, from Matthieu at Chanel to Selena at the Golden GlobesThe “supernova” mindset Michael Kors gave her 20 years agoWhat’s actually in a stylist’s toolkit and the brands she swears byHer go-to jeans, white tee, and blazer, and where to shop each oneThe fastest way to elevate any outfit instantlyPre Order The Art of Intentional Dressing: https://a.co/d/00MdJuwSTimestamps:00:00 Intro, intentional dressing and why clothes are emotional02:00 Three words: the rule Erin uses with every client04:00 The “good bag” moment and dressing from feeling06:00 Why aesthetic quizzes fall short without emotional connection08:30 Finding your style superpower10:30 Owning femininity as a power move12:00 Getting out of a style rut13:30 What to do when you hate your outfit halfway through the day15:00 Color analysis, trends, and what’s actually worth your attention16:30 Inside a first fitting with Erin Walsh18:00 Dressing through body changes with compassion20:00 “Breaking the shell”: vulnerability and style22:00 The CREATE method (Clarity, Ritual, Editing, Alignment, Truth, Expansion)25:00 Handling real-time criticism on the red carpet27:00 Why joy is the future of fashion (Matthieu at Chanel, Selena at the Globes)29:00 The “supernova” mindset from Michael Kors29:30 Inside the Devil Wears Prada 2 press tour31:30 Planning a global press tour at this scale33:30 The Easter eggs: the runway office, the blue Chanel sweater, the bangs35:00 Valentino in Japan, Balenciaga in Korea, Susan Fang in China37:00 The Valentino Rockstud comeback38:30 Toe cleavage, heels, and why flats don’t work for her40:00 Final stops: New York and London40:30 The stylist’s toolkit: what Erin travels with41:30 Her go-to jeans, tee, and blazer brands42:30 The fastest way to elevate an outfit43:00 Outro

Zac Posen has always understood that fashion is about more than just clothes—it’s about creating moments.This week on Let’s Get Dressed, I sit down with Zac to talk about what it means to reinvent American fashion today. Now as Creative Director of Gap Inc., overseeing Gap, Old Navy, Banana Republic, and Athleta, Zac shares how he’s bringing his signature sense of “fashiontainment” to a global scale.From viral cultural moments to designer collaborations like Old Navy x Christopher John Rogers, we discuss how fashion is shifting—from exclusivity to accessibility—and what it takes to build a brand that resonates in today’s world.Plus, Zac shares his go-to styling tips, from the one piece that instantly elevates your jeans to why every woman needs her own version of the perfect little black dress. We also get into the future of fashion, the role of AI, and why instinct and taste still matter more than ever.In this episode, we get into:What reinvention actually looks like in fashion (personally and professionally)The shift from couture to designing at scale—and what changes creativelyWhy fashion is moving into entertainment and pop cultureHow collaborations (like Old Navy x Anna Sui + CJR) actually come togetherThe “cultural receiver” mindset and how to spot what’s nextWhy some fashion moments go viral—and others don’tWhat it takes to execute big ideas inside a corporate structureThe role of failure, resilience, and timing in building a careerHow AI is already shaping fashion—and where it still falls shortWhy direct-to-consumer and social media changed everythingThe difference between product that looks good vs. product that actually sellsZac’s philosophy on creativity, risk-taking, and staying relevantEasy styling advice: how to elevate jeans, wardrobe staples, and everyday dressingThe Old Navy x Christopher John Rogers collection is live now: https://oldnavy.gap.com/Timestamps: 00:00  Intro, Zac Posen in LA and setting up fashion as storytelling01:08  First Oscar weekend and Hollywood influence02:00  Disney, imagination, and fashion as magic04:00  Fashion as entertainment and cultural relevance05:00  Reinvention, joining Gap, and creative evolution08:40  Gap Inc. as a “country” and leading at scale10:45  Old Navy, first impressions, and bringing in designers13:00  Process over persona, being hands-on creatively15:00  Executing ideas step-by-step and creative instinct16:20  Collaborations and creating cultural moments18:40  Failure, risk, and resilience in career growth19:00  Do fashion brands need to entertain today?22:00  Fashion vs entertainment and the shift in culture23:20  The viral dress moment and why product wins25:00  Gap Studio and building cultural fashion moments27:00  Anna Sui collaboration and AI in fashion30:45  Christopher John Rogers x Old Navy exclusive35:00  The state of American fashion today37:00  Design evolution: construction over trend39:00  What success looks like now (seeing it on the street)41:00  Creativity as a daily practice42:00  Styling tip: how to elevate jeans43:00  Closet staple: the little black dress43:50  Menswear tip: just wear a button-down44:20  Outro

We’re in an era of endless options, constant drops, and algorithm-driven trends…but what are people actually buying?I sit down with retail expert and Puck writer Sarah Shapiro to do a real-time “channel check” on the fashion industry. From what’s selling in stores right now to the pieces quietly dominating across data, and the brands actually getting it right, we break down what’s working, what’s not, how to actually make sense of it all, and where you should be shopping.In this conversation, we get into:What a “channel check” is and why it reveals what people are really buyingThe shift away from leggings and what’s replacing themThe rise of the “easy pant” and why it’s everywhere right nowThe stores and brands that are actually getting it rightWhy curated retail experiences matter more than everWhat’s not working in retail right now (and why overproduction is a problem)The brands quietly winning vs. the ones struggling to keep upWhat the data actually says people are buying (and the pieces that keep selling out)The “airplane outfit” effect and why it’s one of the most powerful drivers in fashionThe price point people are really shopping right nowWhy resale is changing how we think about buying clothesHow AI is starting to shape the future of shopping (and where it still falls short)Why personal style still matters more than trends or algorithmsHow to filter the noise and figure out what actually works for youShop the episode here: https://substack.com/home/post/p-192896437Timestamps 00:00  Intro, “retail whisperer” and setting up the spring channel check02:00  What a channel check actually is and how to read a store04:00  The rise of “easy pants” spotted IRL (channel check in the wild)05:30  Why people are moving away from leggings (but not fully)07:00  Girlfriend Collective leggings, High Sport pants, and the “cookie theory”08:30  What stores are actually doing well right now (Mohawk, curated retail)10:30  Discovery in stores vs overwhelming assortments11:30  The problem with endless scroll and too many options13:00  What defines a “mall brand” today and how retail categories have changed15:00  What people are actually buying right now (ShopMy + Puck data)17:00  Seasonal shift: what spring shopping will look like18:30  The “airplane pant” and why product framing sells20:00  Brands to watch right now (Still Here denim and expansion beyond hero pieces)21:30  The $300–$800 “middle market” and how people are shopping it22:30  Why resale is changing how we think about buying clothes24:00  The RealReal mindset: depreciation, longevity, and wearing your clothes25:00  Her background: from retail to Substack to Puck27:00  AI in retail: where it works (logistics, tagging) vs where it doesn’t (taste)29:00  Why AI styling still misses nuance and personal language31:00  The future of retail: tech vs human experience in stores32:00  How to filter the noise and actually figure out your personal style33:00  “Let’s Get You Dressed” — what to wear to a big business meeting35:00  Investment pieces, blazers, and how to shop strategically (RealReal, vintage)

Spring is officially here, which means it’s time for a wardrobe reset. I’m breaking down the 10 pieces you actually need for spring whether you’re shopping your closet or investing in a few key pieces.I’ve always found spring to be the hardest season to get dressed for. It’s that in-between moment where your winter pieces feel too heavy, but it’s not quite summer either, so figuring out what actually works can be hard. From the perfect work pant to the return of the barn jacket, pencil skirts, and cropped denim, these are the staples, trends, and styling shifts that will make getting dressed this season so much easier. We’re also talking about how to transition your wardrobe from winter to spring, why fabric matters more than you think, and how to bring more personality into your everyday outfits.This episode is your guide to refreshing your closet without overconsuming, focusing on pieces you’ll actually wear and style on repeat.Shop all items mentioned in the episode: https://shopmy.us/shop/collections/4234938In this conversation, we get into:The 10 spring wardrobe essentials you actually needHow to transition your wardrobe from winter to springWhy switching fabrics is the key to seasonal dressingThe best “work pant” styles for spring (and why they’re so versatile)The return of the barn jacket and how to style itWhy pencil skirts are trending again and how to wear themThe layered tee trend and easy ways to elevate basicsHow to incorporate texture (fringe, feathers, movement) into your wardrobeWhy baby blue is the standout color for springHow to use accessories like belts and shoes to elevate any outfitThe return of lace and how to style it beyond “going out”Why cropped jeans are back and how they change your proportionsThe shift toward sleek, minimal shoes (and the best loafers for spring)How to refresh your closet without buying everything newTimestamps:02:00  Life update + getting back into routine after being sick05:00  Why spring is the perfect time for a wardrobe reset07:00  The importance of fabric when transitioning seasons09:00  The perfect work pant: what to look for + best styles12:00  The barn jacket: why it’s a spring staple15:00  Pencil skirts are back: how to style them for real life18:00  The layered tee trend and elevated basics20:00  Texture in fashion: fringe, feathers, and movement23:00  How to wear statement pieces in an everyday way25:00  The color of the season: why baby blue works as a neutral27:00  Bright accessories and the power of a statement belt29:00  Lace for spring: how to style it beyond the obvious31:00  Cropped jeans and why showing your shoes matters34:00  Affordable vs. investment denim options36:00  The return of the sleek loafer (and why chunky is out)38:00  How to shop your closet and avoid overconsumption40:00  Final thoughts: building a wardrobe you actually wear

Carolyn Bessette-Kennedy is everywhere again but the conversation around her style often misses what actually made it so compelling in the first place.I sit down with writer and repeat guest Larissa Mills to talk about the frenzy surrounding CBK right now, from the new Love Story series on FX and Hulu to the endless stream of content promising you can dress like her if you just buy the right boots, coat, or sunglasses. Together, we unpack what people are getting wrong about Carolyn’s style, and why it was never really just about the clothes.In this conversation, we get into:The Carolyn Bessette-Kennedy style revival happening right nowWhat people are getting wrong when they try to copy CBK’s lookWhat it was actually like to live in New York during the Carolyn eraWhether Carolyn was seen as a style icon in real time — or became one laterWhy her style felt powerful because of her aura, confidence, and restraintHow social media and overconsumption have changed the way we approach personal styleThe difference between being inspired by someone’s wardrobe and replicating itWhy repetition, discernment, and editing are the real keys to great personal styleHow to take inspiration from Carolyn’s wardrobe without losing your own point of viewThe brands, silhouettes, and styling tools we’d use to channel the spirit of CBK in a more personal wayTimestamps 05:00  CBK resurgence, Love Story and the social media frenzy07:00  Why “dressing like Carolyn” misses the point of her style09:00  Larissa Mills on personal style and impenetrable taste10:00  What women were actually wearing in NYC during the CBK era12:00  90s minimalism, Calvin Klein, and the “uniform” of the time14:00  Was Carolyn a style icon in real time—or did that come later?17:00  The role of aura, presence, and her relationship with JFK Jr.20:00  Why CBK’s style felt powerful beyond just the clothes23:00  The difference between copying vs. embodying personal style26:00  Overconsumption, the internet, and losing individuality in fashion29:00  How to build personal style through repetition and restraint32:00  Tailoring, fit, and the reality of making clothes work for you34:00  Heels vs. flats and the practicality of everyday dressing36:00  Breaking fashion “rules” and wearing what you actually love38:00  Editing your wardrobe and developing discernment40:00  Signature pieces, silhouettes, and building a personal uniform42:00  Why you’ll never be CBK and why that’s the point43:00  Introducing “Let’s Get You Dressed” (listener styling segment)Follow Larissa on Instagram https://www.instagram.com/larissamills/

Paris Fashion Week just wrapped and the fashion industry feels like it’s at a turning point.I sit down with friend of the show and fashion editor-at-large at 032c, Brenda Weischer, to break down the biggest moments from the season - from Chanel’s viral shoes to Tom Ford’s standout show, and the collections that sparked the most conversation across the industry.In this conversation, we get into:The shows that defined Paris Fashion Week this seasonWhy Chanel might have quietly won fashion monthThe runway moments everyone is talking about right nowThe collections that felt exciting — and the ones that fell flatWhy luxury fashion prices are reaching a breaking pointHow fashion houses balance creativity with pressure to sellThe debate around what “sexy” means in fashion todayHow creators and commentators are reshaping fashion coverageWhat actually happens behind the scenes at fashion showsAnd how to take runway inspiration and translate it into your real wardrobeTimestamps02:00 Paris Fashion Week recap & the current state of the fashion industry09:00 Runway inspiration and recreating fashion week looks at home10:00 Hair, makeup and runway aesthetics shaping personal style11:00 Tom Ford and the return of character on the runway12:00 What “sexy” means in fashion today20:00 How editors and creators get invited to fashion shows22:00 Inside fashion week seating charts, VIPs and brand politics25:00 Luxury brands pulling back from wholesale and retail partners27:00 Who actually attends shows: clients, editors, celebrities32:00 Balenciaga, cultural references and fashion storytelling35:00 Music, staging and spectacle at major runway shows37:00 Creative directors and controlling the full brand vision39:00 The Chanel shoes everyone is talking about40:00 Chanel bags vs practicality and everyday fashion42:00 Nostalgia, personal style and dressing with joyFollow Brenda on Instagram https://www.instagram.com/brendahashtag/Thank you to my partners at Macy’s for my newest wardrobe essentials for spring! #Macyspartner

Before she was even 30 years old, Willa Bennett took over not one, but two of the most iconic magazines in media: Cosmopolitan and Seventeen.In this episode, I sit down with Willa to talk about what it actually takes to run a legacy magazine in 2026 — in a culture driven by viral discourse, instant backlash, and internet-speed opinions.In this conversation, we get into:What it felt like to take over Cosmopolitan at 29What an Editor-in-Chief actually does day-to-dayHow she decides who and what gets visibilityWhy story matters more than star powerThe Sydney Sweeney cover and how she thinks about controversyWhether editorial “rage bait” is realHow viral culture and engagement metrics shape modern mediaWhat Gen Z readers are actually curious aboutAnd why “taste” might be the most important skill in journalism right nowTimestamps01:30 Growing up with magazines & coming full circle04:30 Getting the Cosmopolitan job — the emotional moment07:30 Running a legacy brand in a digital-first industry10:30 What an Editor-in-Chief actually does in 202615:30 Instinct vs analytics — how editorial decisions are made20:00 AI, dating culture & what young readers want23:30 Story over star power & viral visibility27:30 The Sydney Sweeney cover & navigating backlash32:00 Is editorial rage bait real?35:00 Celebrity culture, controversy & documenting the moment37:30 Are we still in the Gen Z era?40:00 The future of media & why taste mattersFollow Willa on Instagram https://www.instagram.com/willahbennett/?hl=enThanks to Banana Republic for my favorite pieces from the spring collection. Shop their new arrivals at www.bananarepublic.com #BananaRepublicPartner

At 22-years-old, Madison Dowd bought Ludivine, a long-standing Upper East Side boutique, through BizBuySell.com. Instead of starting a brand from scratch, she stepped into an existing business with loyal customers, real inventory, a balance sheet, and an unwavering belief in the future of retail.This conversation gets into what it actually looks like to run a multi-brand fashion boutique today — from buying decisions and trade shows to navigating instinct versus data. We also talk about learning a customer and buying patterns, what makes the Upper East Side the most valuable retail landscape, and the brands flying off her shelves. Timestamps:01:30 — Buying Ludivine at 22: Why she chose to purchase instead of start from scratch05:45 — Finding the business on BizBuySell and stepping into an existing P&L10:00 — Learning before changing: understanding a legacy customer base14:40 — The Upper East Side shopper: loyalty, psychology, and neighborhood dynamics19:15 — Buying strategy: trade shows, inventory bets, and seasonal planning23:50 — Instinct vs. data: when to trust your gut 28:00 — Social media’s role in a brick-and-mortar business30:45 — What actually makes a multi-brand boutique sustainable todayShop Ludivine https://boutiqueludivine.com/Follow Madison on Instagram https://www.instagram.com/madisondowd/Follow Madison on TikTok https://www.tiktok.com/@shopgirlmadison