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Talking About Clothes with Holly Chayes
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Talking About Clothes with Holly Chayes

Author: Holly Chayes

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Talking About Clothes with Holly Chayes is a seasonal podcast, where I talk about clothes with people who wear them. Regardless of how fashionable or stylish we think we are (or are not), we all wear clothes. In this podcast, we explore the depths of some of the most intimate times in our lives without shame or guilt. Each season focuses on a theme, where guests share their personal perspective on that particular topic.
34 Episodes
In this season of the podcast, we’re having conversations about changes in our wardrobes and lives. These conversations took place at the end of July and beginning of August 2020.  In this season, we talk about: Taking the time and effort to investigate your own style and preferences How stark the difference can be between our aspirations and our reality, even when we achieve the transformation we’ve been desiring And after all the time and effort how sweet the rewards that come along with being courageous enough to change your style are.  Keep an eye out for full episodes dropping at  Talk to you then.
In this conversation we talk about identity crises, buying second hand, and high end bargain hunting, the masks we can put on when we choose our clothing, looking good versus feeling good in your clothes, and noticing how other people respond to how you dress.  Find more at
In this conversation we talk about loving shopping, shopping as part of your weekly routine and a way to carve out time for yourself, the power in having the items in your closet that you know you always get compliments on and the feeling of endless possibilities that come with new items. Plus there is a ton of fantastic sisterly banter.  Find more at
In this conversation we talk about appreciating garments without feeling the need to obtain them, developing your own POV and your own style, online shopping and how to solve the issue of finding clothes that fit online, and the understanding that if a piece of clothing you’ve had your eye on is gone, something else will come along. Find more at
In this conversation we talk about  impulse buys, investment pieces, and trends, not buying yourself clothes and then having nothing to wear when you need it, finding the balance between professional and personal in your wardrobe, and giving yourself a pause to cut down on impulse purchases.  Find more at
In this conversation we cover optimistic purchases, the trouble with not knowing what you don’t know, splitting your shopping between majority thrifting and minority high end, and the contrasting experiences between shopping in high end shops and thrifting.  Find more at
In this conversation we talk about changing your shopping mindset and how that influences your shopping experience, trying on anything that catches your eye, rather than pre-judging things (it caught your eye for a reason), going with shops and designers who design intentionally for larger sizes, and the pros and cons being picky when it comes to your clothing choices. Find more at
In this conversation we talk about keeping quality items regardless of trends, and also going about trying to find those quality clothes and then sticking to what works. Plus the frustration of shopping and not being able to find what you’re looking for, and how big life transitions and body changes affect the experience of shopping. Find more at
In this season we're having conversations about shopping in the Pre-Covid-19 version of normality. These conversations took place between the tail end of 2019 and the first months of 2020. We talk about: loving shopping, hating shopping, dreading shopping, and embracing shopping. shopping seasonally, cyclically, weekly, and hardly ever at all bargain hunting, but also the fact that clothing requires resources – of fabric, materials, and labor – and resources cost money, regardless of if we pay the full price. Plus personal stories, tons of laughs, and so much more. Keep an eye out for full seasons dropping at
This is the final episode of season three of Talking About Clothes. In it, I talk about how the hardest part of this whole year-long project was showing up everyday and doing the thing I showed up to do. And also, how after a transformative year (which this year of The Self-Made Wardrobe Project certainly was), there’s no going back to the way things were before. That year changed how I related to my clothes in fundamental ways. Thank you for revisiting this project with me, now I hope you’ll take some time to explore these remarkable Black creators and thinkers working in clothing-related fields. Because Black lives matter. And these creators are doing incredible things. In Style, Handmade Style & Sewing Brittany Diego is a celebrity stylist and fashion consultant. She also hosts the Fashion School Dropout Podcast. Website: Instagram: @brittanydiego Podcast: Fashion School Dropout Stephanie Thomas, the founder and CEO of Cur8able, is a disability fashion stylist, speaker, and consultant. Website: Podcast: Cur8able the Podcast Instagram: @disabilityfashionstylist Jasika Nicole, is an actress and also makes her entire wardrobe. Website: Instagram: @jasikaistrycurious Marcy Harriell, as she says in her IG bio, is an actor, singer, sewist, and merrymaker. Website: Instagram: @marcyharriell Black Girls Sew™ is “committed to making an impact on the lives of women and youth through education in sewing, design and entrepreneurship.” Instagram: @blackgirlssew In Clothing Sustainability Dominique Drakeford, Founder of MelaninASS, and Co-Founder of Sustainable Brooklyn. In her own words, she “work[s] at the intersections of sustainability and style to heal our relationship to the Earth and spark equitable change for economic wellbeing.” Website: Instagram: @dominiquedrakeford Aja Barber is a a writer and fashion consultant focusing on race, intersectional feminism, and fashion. Instagram: @ajabarber Patreon: In Fashion & History Cheyney McKnight, founder and owner of Not Your Momma’s History, is a Historical Interpreter and Living Historian. Website: Youtube: NotYourMommasHistory Instagram: @NotYourMommasHistory Patreon: Dandy Wellington is a bandleader, entertainer, event producer, and creative consultant. #VintageStyleNOTVintageValues Website: Youtube: Dandy Wellington Instagram: @dandywellington Patreon: Additionally: Anti-Racism Training, Resources & People to Follow "Undoing Racism" by The People’s Institute for Survival and Beyond “Race Demystified" by Milagros Phillips Rachel Elizabeth Cargle a public academic, writer, and lecturer. Website: Twitter: @rachelcargle Instagram: @rachel.cargle Layla F. Saad is an "author, speaker & teacher on the topics of race, identity, leadership, personal transformation & social change." Website: Instagram: @laylafsaad The Conscious Kid: "Parenting and Education through a Critical Race Lens" Instagram: @theconsciouskid Patreon: Nupol Kiazolu, President Black Lives Matter Greater NY and Founder/CEO of Vote 2000. Instagram: @nupol_justice Twitter: @nupol_justice A document with dozens of additional resources. This document was compiled by Sarah Sophie Flicker & Alyssa Klein in May 2020:     Learn more at
One of the things that I wore pretty much every single day prior to doing this self made wardrobe project was jeans. But at the beginning of this project, when I was building up the number of garments that I had access to (within the parameters of this year long wardrobe project), I focused a lot on wearing and making fast, simple, easy garments - skirts, tops, simple sweaters, etc.  And so I went months without wearing jeans, which, if you'd asked me prior to this project, if that were possible, I would have said no. But it turns out it was entirely possible. Regardless of what I had previously assumed. Learn more at
I know I'm not the only one who makes snap judgments about my clothes. Especially when I first try a garment on that's not my usual cut or silhouette or style. That's what happened with one of the dresses I knit for this self made wardrobe project. It was a one piece hand knit, A-line, very colorful mini dress that was neither my normal colors, nor my normal silhouette nor my normal style, but ended up being one of the pieces that I love the most in this wardrobe and wore quite often and still wear today. So I guess one of the lessons from this dress is to not jump to conclusions about garments before you wear them a couple times. It's easy to forget that our bodies have preferences about what they wear. And often, so not always, those preferences are merely because that's what our bodies are familiar with. It's sort of like if you start working out your body is going to have opinions on it. And the same is true for whatever garment you're talking about. It doesn't have to be high waisted jeans or period corsets or turn of the 20th century undergarments, it's true for anything. If you're not used to wearing a suit, your body is going to take a while to get used to wearing a suit. If you're not used to wearing lounge-wear, your body's going to take a while to get used to wearing lounge-wear. So I think that when something's new, and it has to do with our physically feeling weird in the clothing and you want to play around with the style, maybe give it a couple tries, and see if you get used to it. Learn more at
Like with food, a really good high quality fabric is going to give you incredible results even if your skill level isn't that of master chef or a master couturier. However, you can also make not so good materials work, it just requires a lot more finesse or experiences. This robe is one that I get compliments on every single time I wear it. There are little tiny metallic threads running through it but they're just enough to be interesting and not so much that it becomes gaudy. There are these little novelty squares of plush fabric, glued on to the the chiffon. And it's so sweat inducing because the fabric 100% polyester, (which means that's 100% plastic). But if the breeze picks it up just right, it floats and flutters behind you and looks marvelous. And I'm always astonished when I remember that, this was an impulse fabric purchase that I put together into a robe on a whim and wore about 30 times throughout the course of the year. Learn more at
I'm pretty sure if I had had all of the time in the world, I wouldn't have come up with this dress solution. There's something about a deadline that clarifies exactly what the parameters of the project are, and forces you to meet those requirements. That forces you to meet those requirements, but doesn't allow you to follow any extraneous rabbit holes. There were no "nice to have" details on this dress. The slip was very simple and very straightforward. But it did the job. And I'm not sure I could have asked anything else.   Learn more at
Wasting Time

Wasting Time


Time seems like a very bizarre concept right now. It has that funny quality of not really being solid anymore and not being something that we can agree on the unit of measuring time by and I'm thinking a lot about time that could be called wasted time. I'm thinking in particular of one long white, plain white skirt that I sewed, intending it to be worn under a knitted dress I had made, because I wanted something more for that dress, and that I only wore a couple times. The skirt probably took a couple hours to make. And I'm wondering if I had known how little I would have worn that skirt and how unnecessary that skirt was, if I would have done something different with those couple hours instead. And I don't know. Because how could I have known that I wouldn't have needed that skirt, if I hadn't had that skirt and not needed it? Learn more at
"Oh, I don't have patience for that." I can't tell you how many times I've been told that while knitting or sewing. But the trick is, you don't knit or sew because you have patience. You have patience because you knit or sew. It's a way of practicing and acquiring something that you don't already have. It's a way of bringing more attentive mindfulness to a moment. And if you practice enough, then you're able to bring that attentiveness to moments when you're not engaging in your craft as well.  Just like any other practice, you don't practice because you're good at something, you practice to get better at it. So it's precisely because I don't have patience for things that I practice paying patient attentiveness to my craft.
Knitting this sweater was a hot mess. It was messy, it was ugly. It involved a lot of cursing and re knitting and reworking and shoving the project into a drawer for a couple days. And in all honesty, if I wasn't in the middle of this year long wardrobe challenge with an already extremely limited wardrobe, I probably would have abandoned this sweater altogether. And yet, a sweater in the end I had. It was messy. It was complicated. It was not fun. It was not funny. It was something I can laugh about now, but the process sucked. But after it was all said and done, but the sweater was fine. In fact, it was fantastic. I still have it in my closet, and I still wear it every winter. When do we give up on a messy process? And when do we keep going because that's the only thing to do? And if we get to the end and have a wearable completed wonderful sweater, how much does the messy process of getting their impact the final result? Because no matter how messy the making process is, if you have a full sweater at the end, you have a full sweater at the end. Regardless of how much cursing it took you to get there. Learn more at
Looking back on this year long project, I'm almost as much amazed by the garments I didn't wear as the garments I wore dozens upon dozens of time. You would think that with a super limited wardrobe I would reach for every garment I could. And yet, I didn't. I realized that this year was not just about taking a pretty outfit photo every day. It was about creating clothes to live the whole year in. While this dress that had a very Audrey Hepburn feel to it in photos, it was not a nice dress to wear, so I didn't wear it. And a garment's use isn't to hang in a closet, it's to be worn So if you're not going to wear an item, why do you have it? Learn more at
One of the first things I had to contend with when setting up this project was: what was I going to count as a garment that I needed to make? I came up with two rules for this project: accessories and undergarments don't count. if it feels like cheating, it probably is. And one of the biggest takeaways I got from this year was that you when you're trying something new or different or challenging or not the way you've done things before, do everything you can to set yourself up for success. You can find more at
I had originally planned on bringing you the third collection full of incredible conversations with wonderful guests all focused around the topic of shopping. However, things have changed dramatically, over the past few weeks. So instead of releasing the planned third season, I'm going with the "new situation requires a new plan" approach to life and recording an intermittent third season. Revisiting an extreme wardrobe challenge I did five years ago called The Self Made Wardrobe Project. During this project, I wore no store bought clothes for a whole year. I'm not sure exactly what the release schedule of this third season will be or how long this season will last. But I'm looking forward to revisiting this project with you, and it's really nice to have something to look forward to. You can find more at
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