I was so excited this month when my friend Hillary Dixler Canavan won the drawing for the live styling session! We talked about how her years working in theater and restaurants influenced her style, how she was able to escape (some of) the pressure to change her body, and how her mom helped with that.
In this conversation, we get into one of my pet peeves, the idea that our outfits are never “styled” enough, or that our outfits are missing something, in part thanks to the “wearing vs. styling” trend on social media.
Hillary’s a regular in the unflattering outfit threads and writes the incredible home cooking newsletter “What Are We Having?”, please check it out!
I unlocked a few related personal style posts from the archives:
This video is for paid subscribers, and the chance to enter to win a session like this is only for annual paid subscribers. If you like what you read, and want to have the chance to win a free live styling session, here’s a discount to upgrade now!
A quick note — I recently opened my schedule back up for one-on-one personal styling clients after submitting my book’s first draft! If what I do in these recorded sessions intrigues you, feel free to book a one time session here or set up a 15-minute free call to talk about how we can work together more long term.
I used AI to clean up this transcript to make it easier to read. Let me know if you prefer this over the transcript Substack generates (which I assume is also AI).
Hillary:
I’m excited. I’m very excited about it.
Dacy:
Tell me what’s making you feel excited.
Hillary:
Well, not to overly fangirl, but I have been following your work for a really long time. I think even before writing group, I was following you on Instagram.
Dacy:
Oh, yeah?
Hillary:
And I had always said that if I ever got a job where I needed a work wardrobe, I would hire Dacy to help me learn how to get dressed.
I’ve always had very creative jobs, so I’ve never needed a traditional work wardrobe exactly. But I always had it in my mind: “If I ever get a more corporate job, I’m going to hire Dacy and she’s going to help me figure this out.”
Dacy:
I had no idea.
Hillary:
I’m blushing telling you this.
I’m really excited about this session because when you sent out the choices of what we could spend the hour doing, I was really drawn to the idea of styling what I already have.
I feel like doing those outfit posts in your group has given me a lot more confidence that I am already pretty confidently expressing my style. Where I feel more stuck is that I’m very comfortable repeating outfits. I do it often, and I don’t feel bad about it, but I know that sometimes I’m repeating outfits because I feel like I don’t have another idea.
And with this volume of clothing, there are probably more ideas. So I’m excited to get someone else’s take on it or have you ask the questions that make me think of new things. I don’t know your approach to that.
Dacy:
Yeah, yeah. Okay. Just an aside for anyone watching or watching the replay: if you are an annual paid subscriber, you can enter to be in the drawing to win one of these. I’m going to do one every month—free styling sessions.
What was I going to say? Yeah, in a minute I want to pick up on what you were saying about sometimes feeling like, “I don’t have another idea about styling.”
And just for housekeeping—you know me—but I take a lot of notes sometimes just to keep my train of thought going.
We’re going to do this like a normal client session, so I’d really love to start by asking you about when you first became aware of your clothes.
