unflattering

My kids are back in school and I finally have my days to myself. I’m ready to get back to a regular work schedule instead of fitting it in here and there. To help me get in the mindset, next week (8/31-9/4) I’m going to get dressed like I work in an office even though I work from home. I’m going to post my outfit in the unflattering chat each morning and I’d love you all to join in. Post as many of the days as you like.

Coming up: in the next few weeks, I’ll be publishing posts with my summer outfits, what I purchased recently, and a big post announcing my rebrand! I’m also planning to do a Substack live AMA and a live talking through the wardrobe pieces I’m getting rid of. Make sure you’re subscribed so that you don’t miss anything! Call for submissions: so many of you resonated with our most recent unflattering story from Diana Fox Tilson, LICSW. I’d love to publish more readers’ work.

This is unflattering stories. I asked unflattering readers what they would want to share about their own evolution of style or barriers to it and I’ll be sharing their thoughts regularly. I met Diana Fox Tilson, LICSW in the comments of this newsletter. I always found her comments thoughtful and insightful. When I started the unflattering chat in 2024, I got to know Diana a bit better, and now she’s a staple in our Friday outfit threads.

This thread is for subscribers in the unflattering membership. If you’d like to upgrade so that you can ask me to find something for you, you can do that here. For $150/year, you get access to this thread where I’ll suggest items for you based on your request, access to 3 of my online mini-courses, my spreadsheet of over 250 retailers (Virginia Sole-Smith called it “gold”), and all the regular paid subscribers’ perks like the ability to comment and to see my monthly shopping picks.

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.

Quick post this week - I’m currently in Oregon for 16 days. We were in Portland for three days, and then moved on to Hood River, where my sister lives, for the remainder of the time. It’s been a while since I was away from home for this long, so I thought extra hard about packing. I recorded a video (~7 minutes) of my process to share with y’all.

This is style stories, an interview series where I ask guests about their relationship to clothes over the course of their life and how external influences have shaped it. I focus on the ways that women are able to reject societal expectations about what they should wear. Every guest answers the same questions. My friend and writing group member Ryan Rose Weaver (she/hers) introduced me to Leigh because she experienced in person Leigh’s welcoming inclusive retail environment.

Life has been hectic lately. I’d quiet switched the day of the week I publish on (Wednesday instead of Tuesday so I don’t have to scramble on Monday) since I’m the boss around here, but last week a post didn’t go out until Friday and it’s unclear whether I’ll be able to get this one out today (Thursday). Speaking of Substack schedules, not only will we be visiting my sister in Hood River for two weeks in July, but my book is due July 31st. I’ll definitely be quieter here for a few weeks.

The complete transcript of this video chat is available by clicking the “Transcript” button below the video. Hi everyone — I have had the craziest week. I had the live styling session recording from last week ready to go out on Wednesday, but on Monday, my family and I traveled to Kansas City to see a World Cup game. The next day, on the morning of the game, I got an email from Stubhub saying they didn’t have tickets for me (which I’d paid for in November 2025).

While yes, I did recently do an entire month of thrift content, I’ll never want for ideas of more. Enjoy! I think of thrifting and secondhand shopping a bit like a game with different levels. Level 1 is your nicely curated secondhand store (i.e., Buffalo Exchange, Clothes Mentor, etc.) Level 2 is a nicely organized (clothes are sorted by category and size) thrift store like Savers.