Notes On "Flattering"
Prioritizing comfort With Dacy Gillespie.
I’m so excited to share ’s Style Questionnaire with you!
She probably needs no introduction, but is an anti-diet personal stylist and the author of .
Dacy prioritizes her clients’ physical, sensory, comfort, and aesthetic needs over creating optical illusions to make their body look like it conforms to patriarchal standards of beauty. Dacy is also neurodivergent and manages anxiety, depression, high sensitivity, introversion, and ADHD while currently in peri-menopause and parenting two young children. Fun! Along those same lines, she’s a Cancer, INFJ, human design projector, Obliger, Enneagram 4, and her top CliftonStrength is empathy (maybe you can tell she likes personality tests?). She moved to St. Louis, MO 18 years ago for a boy, but before that lived in Portland, OR, outside of Cleveland, Houston, NYC, and Miami.
I first started reading
on ’s recommendation and I found Dacy’s work to have such a refreshing perspective on comfort and consumption. I love her approach to getting dressed and I think many of you will, too!If you like reading about midlife crisis crop tops and medium femme, please become a paid supporter of Big Undies!
What are you wearing right now?
A thrifted blue striped button down shirt, lavender bike shorts from Target, and red Birkenstocks secondhand via Poshmark—so basically, my summer uniform.
What was the last item of clothing you bought?
Technically the last thing I bought were these Crocs, but I’m returning them—not enough arch support. So the actual last thing I bought was this tomato red cardigan (similar up to 3x) from a local vintage store for $16. I’m going to attempt to bring a bit of my summer red that you and Virginia pushed me on in our style challenge into fall.
If you had to wear a uniform (same thing every day) what would it be?
This is tougher than I thought it would be! I had to look through a bunch of outfits to see, and it turns out most of my outfits are a combo of denim and some shade of white. I’m really loving off white on bottom, denim on top, with colorful accessories these days.
Where did you get clothes as a kid? Describe a favorite childhood outfit.
This brings up some sad fashion memories for me. Growing up in the deep south, we didn’t have much money (although I had many other privileges), and even if we had had more resources, my parents didn’t believe that aesthetics of any form (home, clothing, etc) deserved any thought.
I’ve been acutely aware of clothes and what others are wearing as long as I can remember, so I knew what I needed to wear to fit in, and was never able to acquire it. My clothes were a big signifier that we didn’t have much money, and other kids noticed it and teased me about it. I’ll never forget the time I was taunted on the school bus that my clothes came from Kmart. Another big insult at the time was that someone’s clothes came from the DAV (the Disabled American Veteran thrift store), which, actually, mine didn’t. I didn’t discover the joy of thrifting until college.
Where did my clothes come from? I know I got some hand-me-downs from my boy cousins, which was humiliating. I think there were other hand-me-downs from people we knew. At back-to-school time, we would be able to go to Sears and buy a few things, but they had to be from the clearance rack. My biggest wish on every birthday was that I could go shopping with my grandma who lived in Los Angeles, and I acquired a few nicer things that way.
You write the amazing newsletter! Can you tell us a little about what flattering / unflattering means for you and your clients?
In the common usage of the word, “flattering” means something that makes you appear as the smallest version of yourself. In that way, striving for something “flattering” is upholding white supremacist and patriarchal standards of beauty, i.e. that the ideal is a tall, thin, white body and that if our bodies are not that, we must use every clothing trick in the book to get closer to it (see Sonya Renee Taylor’s Hierarchy of Bodies). When we get dressed with this as our focus, we tend to ignore our own needs for the sake of being a pleasing sight to others.
I believe this is totally backwards. With my clients, we start with their needs: What feels good, what styles they like, what function they need their clothes to perform. As you can imagine, it’s hard for people to imagine that they could prioritize things like that because so many believe that clothes that checked those boxes would look terrible on them, that they could never “pull that off”. But we’re able to move through that to get them to a place where they actually like what they’re wearing. To me, reclaiming the word unflattering as a positive means that we reject all of that BS conditioning and instead wear what pleases us.
Tell me about an item of clothing that you wear only to do a specific activity.
I have to think about this because I feel like I wear most of my clothes to do most of my activities—work, Pilates, sleep. I guess there are two categories. I hate winter and I hate being cold, so there are a few items I rarely wear except when it gets below 10 degrees or so. The other would be my dressy clothes. I have about 3 dresses that I’ll only wear for a certain level of event, and never any other time.
What did you wear to the last party or event you attended?
Gosh, I really haven’t attended an event in a long time! The next one I get invited to I’m wearing this Maria Cornejo dress that I got on The RealReal. For my birthday recently, I wore a secondhand Rachel Comey top with thrifted jeans and thrifted Stuart Weitzman heels that are way too high.
Tell me about an experience that changed your relationship to clothing or getting dressed.
There are two. The first was when I finally became comfortable in my style. As I mentioned, style had been pretty unattainable for me growing up, and so throughout college and my 20’s, I was constantly experimenting and putting a ton of effort into my outfits to appear as fashionable as possible. Like, trying to copy runway outfits type of effort (this is when thrifting became a means of experimentation). Even though most of my experiments were with thrifted clothing, I started to notice this constant churn in my wardrobe. I’d thrift, bring home 10 new items each time, try them out, decide I hated them, and donate them back. Because of my sensory needs for my environment, this excess really stressed me out. At one point I had a full closet and two full wardrobe racks in my basement. I finally came to the realization that I didn’t have to try to “win” at fashion, and could just wear easy, comfortable things and fewer better ones. This did coincide with the height of minimalism, but for me it really wasn’t a trend.
The second experience was the changes my body has gone through over the last 5 or 6 years. I want to acknowledge that I absolutely have always had and still have thin privilege. When I first started working with my clients to reject the idea that our bodies should stay the same throughout our lives, mine had stayed the same for the most part except for some very gradual shifts. There doesn’t need to be any catalyst or reason for bodies to change, but in my case, giving birth to my second child, followed by a global pandemic, followed by peri-menopause shifted mine to a place that I didn’t recognize—an experience most people will have at some point in their life. I felt like I no longer knew how to dress my body. Ironically, I’d done so much work and research and unlearning around body image for clients, but hadn’t experienced it myself. I actually was able to observe myself work through it with some objectivity, which was really helpful for my client work. I also worked with an intuitive eating coach (Rachel Cole), which helped immensely.
As someone who works with people from so many different backgrounds, do you have any advice about styling or wardrobes that you think everyone could use?
This is going to sound like I’m trying to wriggle out of the question, but the only kind of advice that I think can apply to everyone is for you to start noticing your needs and preferences and making choices from that information. I believe it’s easier to get dressed when there are fewer decisions to make, but some people love the variety. I believe bellies are normal and should be celebrated and also, I’m not comfortable putting mine out there.
You can practice doing this in all areas of life: when do you prefer to eat (some people eat breakfast right away and some eat later)? What type of sleep schedule works best for you (we’re always told early risers are more successful, but plenty of people are night owls and that works best for them)? What type of movement feels best for your body (light or intense or some of each)? What type of decoration do you love for your home?
Tell me about an accessory or piece of clothing that you lost or ruined but still think about.
This is a close call more than a loss, thankfully. As I mentioned, I’ve never had a ton of expendable income and I’d never had a designer bag. Also, something you need to know about me is that my love language is gifts. Years and years ago, my husband (then boyfriend) was traveling to Italy to perform concerts with a small group of other musicians. He wanted to bring me something back, so he took some of the people in the group with him to go buy a handbag from Furla.
It’s a beautiful bag and I love it. Around 10 years ago, we were eating outside at a restaurant that had sidewalk seating in an area of town with a high crime rate. I hung that handbag on the back of my chair. I took my wallet out to pay and then we left. Hours later, I was looking for my purse and realized I’d left it on the chair. I was devastated because it had been literally the best gift in my life and had so much special meaning and there was no way it hadn’t been stolen. We called the restaurant and someone had actually brought it inside and it was safe! I got lucky that time, but don’t ask me how many Kindles/Kobos I’ve left on planes.
What’s your fall 2024 must have?
I think that red cardigan was it!
Who do you think has good style?
Alex Stedman has really inspired me to embrace (at least a little) color. Musemo of misslionhunter for her creativity and cool prints. Amanda of Little River Mama for my earthy side. Lucy Chadwick (mostly just her outfit pics from fashion weeks, there’s literally nothing on her IG feed) for classic but slightly edgy art gallerist vibes.
Anything else you want to tell us about getting dressed?
I just think it’s important to figure out how much of this is important to you. You can love reading about style but have a very simple real life style. Or you can play dress up every day. Or you can say “good for her, not for me” and just not bother. It’s all up to you.
Thanks, Dacy! Follow Dacy on Instagram and subscribe to for anti-diet personal style. You can find everything I linked to here.
I’d love to know what you thought about this style questionnaire in the comments.
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Thank you so much for having me Corinne!
I love these style questionnaires. Thank you, Corinne and Dacy.