In this episode, Erin and I talk about how getting dressed should feel intuitive, not overwhelming. We get into why trusting your instincts is the most important part of personal style and how overthinking what to wear is usually what makes it harder. Erin’s whole approach is about feeling supported and confident in what you’re wearing, not chasing trends.

We share a few simple things that actually make a difference. Start with strong basics you can always rely on, like a great blazer, denim that fits you properly, a white button-down, and a suit. Pay attention to proportion, how something sits on your body can completely change how you feel in it. Don’t underestimate the impact of accessories, jewelry and shoes can elevate even the most simple outfit. And when in doubt, go back to what feels like you, not what you think you should be wearing.

We also talk about how style evolves over time, how I’ve changed the way I dress, and why letting go of old versions of yourself is part of the process. We get into travel and packing, and how to keep things simple but still feel pulled together. And we talk about Erin’s book, The Art of Intentional Dressing, and how being more intentional with what you wear can shift how you show up in every part of your life.