Effortless style is not about chasing the next trend. It’s about knowing who you are and letting that confidence speak.
At just 22, Madison Orlando founded Artless, a brand built on simplicity, sustainability, and timeless confidence. Inspired by ‘90s minimalism and the relaxed, sun-soaked California aesthetic, Maddie’s pieces are elevated wardrobe essentials, intentionally crafted to make getting dressed feel effortless yet luxurious, simple, and undeniably you.
In this episode, Emily uncovers Maddie’s journey of creating Artless, navigating the fashion industry at a young age, and building a brand that feels original and enduring. This is more than just fashion. It’s about identity and the quiet confidence that comes when you stop performing and start living authentically.
What you’ll learn:(03:07) - Fast fashion, consumerism, and dopamine shopping (08:19) - Wardrobe staples every woman needs (11:49) - How Maddie started Artless at 22 (18:07) - Overthinking vs Action (Learning by Doing) (19:35) - Lessons from family, faith, and entrepreneurship (20:35) - Trials, setbacks, and the mindset that keeps Maddie going (27:50) - Social media and showing up authentically online (33:32) - Routines and rhythms that sustain creativity (38:35) - Growth, networking, and building with intention (42:53) - Sneak peek of Maddie’s wellness brand, Future Proof (45:16) - Advice for anyone playing small (46:28) - How confidence is built in the quiet moments
Discover effortless style with Artless:Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
My Favorite Murder with Karen Kilgariff and Georgia Hardstark
My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.