SLT067: Simplify Your Wardrobe Redux

Way back in Episode 47, Simplify Your Wardrobe, we explored our relationship with the clothes that we wear and asked ourselves some questions such as: So what things shape your current wardrobe? What does your wardrobe look like now? What would your ideal wardrobe look like? and What are some of your favorite pieces and why? We also introduced that we were going to give a microcourse called Dress With Less a try, cutting our wardrobes down to 33 pieces each for 3 months.

Well, it’s been over 6 months and 20  Simple Life Together episodes since then and while we’ve mentioned quite a bit about our progress along the way, we thought we owed you a good, solid wrap up. So this is it!  Read more…


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Topic:  Simplify Your Wardrobe Redux

When your goal is to simplify your wardrobe, you don’t expect to learn a whole lot of lessons about your attachment to “stuff.” But that’s just what happened with us. Over 6 months ago, Vanessa packed up most of her clothes and put them up in the attic. And then just a few days ago, we sat down and started talking about the process and what we’ve learned along the way. As we talked, I said, “You know what? This is good stuff. We really ought to be recording this!” So we moved on out to our World Shedquarters, sat behind the mics and just had a candid conversation. Vanessa even shared a few journal entries she did early on in the challenge. Here’s a sample:

Day 2: Well I woke up and and the first thing I did, even before going to the restroom was check out my wardrobe. Yup…still pretty empty…nothing really changed. So I cried again. I was grumpy all day…frustrated with the challenge…even more frustrated with my emotions.

But miraculously as the day went on, I started to settle into the idea of living with less. It’s not like this was life or death….it’s a simple challenge….and one I don’t have to commit to if I don’t want to. So that seemed to brighten my spirits a little. And with that….I revisited my closet, made some final edits and settled into the fact that this was just a challenge…only a 3 month challenge.

 So, have a listen and consider this episode a inside look at our own personal triumphs and struggles. It was just Vanessa and me having a little one on one talk, but we thought you’d appreciate being a fly on the wall. If you decide that you want to simplify your wardrobe a bit, too, we’d love to hear some of your lessons learned.


So, what are some things you’ve learned along the way as you try to simplify your wardrobe? How did you handle your struggles? Did you have support along the way? Was 33 the right number of things for you, or was it more or less? We’d love to know!

Be sure to leave a comment below.

Qs and Comments, iTunes Reviews

Thanks to mcevjael who wrote: “Great content…every episode. 5 Stars. It’s obvious how much prep work goes into each episode. Thanks for the valuable content and the easy listening.”


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18 thoughts on “SLT067: Simplify Your Wardrobe Redux

  1. Thank you for sharing your path in this episode. I personally appreciated hearing the challenges you experienced, especially with Project 333. I am also seeking the path to a more simple life, and at times the path can be hard due to unforeseen reasons.
    I have adopted the Project 333 challenge and like Dan, have thrived in it. However, it is a tough project and challenges those who adopt it. I have experienced other challenges and those feelings you shared are applicable beyond this particular Project. So many people feel these challenges and drop out, rather than recognizing this is a personal path. Hopefully this podcast will allow others to recognize it is not a destination but a journey that you make work for you. Thank you again!

    • Thank you, Caroline, for taking the time to write in and congrats on making P333 work for you! You are so right…it’s all about the journey. I think we all get tempted to “call it quits” on some challenges, but sticking with them really does teach us a lot about ourselves.

  2. Oh Vanessa, hugs to you. I completely understand the emotional link between your fitness and your wardrobe. For a woman, we will always think about our appearance. I was just reflecting on this the other day that I don’t feel that I value myself on my appearance and I’m now 45 (so who cares already, no one really expects me to be the hottest woman everywhere I go at this age) but yet I never stop thinking about it. When shopping for clothes, out with friends or getting ready to leave in the morning – it’s always present. All women also feel the twinge of comparison when encountering another female that is incredibly beautiful and put together (even though intellectually we know we shouldn’t compare). I can relate to clothes representing weight loss and how hard you worked to get into shape. It’s also why people have a hard time letting go of clothes that don’t fit them. If it represented a “me” that exercised and ate well, tossing that item can be like giving up on ever being that in control person again. It it’s an item that’s too big, it’s like shedding that layer of protection or brings up irrational insecurities like “the minute I toss this large dress something will happen and I won’t be able to maintain my weight and I’ll need it”.

    It was very touching to hear how the project affected you and I do think these types of challenges definitely need to be personalized for each individual. Even Courtney said that 33 just sounded neat and clean. She didn’t have too much logic or calculation going on when she developed the challenge for herself.

    I want more profiles too! I’m going to send my friend Ihilani your way. I did tell her about your ebook and podcast. She now has a beautiful simple living site as well (I know her from her design/life blog as she used to live on Maui). She’s an eloquent young Hawaiian mother of two who was initially forced into simple living through circumstance but now embraces it.

    • Tania, I swear everything you just said was/is exactly what goes through my brain! My intellectual and emotional thoughts are in constant battle. I switch from “I don’t give a darn what anybody thinks” to “I gotta make sure I look good in front of so-and-so.” It’s exhausting, yet healthy because knowing I have these struggles, I am becoming a little more aware and better able to deal with them. The funny thing is…I’m itching to edit my clothes again! My little therapy session seemed to help me recognize what’s a “healthy” amount of clothing for me.

      Anyhoos…thank you so much for sharing your thoughts and struggles too. I think you are totally “spot on” about the struggles we go through and hope that others who read this will relate and feel “ok” about themselves.

      Looking forward to learning more about your friend, Ihilani too. Thanks so much!

  3. Is it OK to tell your friends you love them in the show notes of a podcast? I hope so, because Dan and Vanessa, I love you two!

    I gotta say, It’s impressive that you can be raw and polished at the same time. Vanessa, I don’t have wardrobe challenges, but I do have other challenges when it comes to my version of minimalism. I look around my house and *at* my house and constantly think, “This is just … way … too … much.” Melinda and I don’t plan to move anytime soon, so I’ll have to come to grips with living in a house that just feels excessive to my current tastes.

    But my major challenges come with all the kids’ stuff. Despite reading our pal Joshua Becker’s Clutterfree with Kids, I still haven’t made much progress to convince my three-and-a-half year old – not to mention his mom – that we don’t need half the things we have. If only I could sync up personal minimalism with family minimalism …

    • We love you too Joel! I had no intentions of getting choked up and crying on the show…but I couldn’t help it! It’s a funny thing though…when you are embarrassed or ashamed of something and then get the courage to tell the world about your struggles…it can be liberating. It felt good to be candid about my struggles with clothes. Just like you being candid about your struggles with the kid clutter. I know how difficult that can be…especially when it’s a family decision. I struggle with the kid clutter too! On one hand I want to teach my children less is more but on the other hand, I don’t want to create an environment where they resent “my” need for less and then they turn around and “keep” EVERYTHING! It’s a delicate balance. It would be so nice to find the secret sauce for syncing personal minimalism with family minimalism. Promise me you’ll share the secret if you find it ok!

  4. Hi there,
    I loved the honesty and vulnerability in this episode, thank you! I did project 333 but since getting pregnant I’ve cut myself some slack. I am like Dan in that I loved the empty look in my closet and drawers. Now I’m in this weird phase where I just want to get rid of all my clothes that don’t fit right and yet I might come back to them once I lose all the preggy weight. What a predicament! Any advice Vanessa? Also, I would love to see more pictures of your home! My husband, dad, and I are in the middle of a DYI bathroom remodel (turing one 100 year old bathroom into two). I’m itching for ideas that are simple! Much love and blessings to you both! Thanks for sharing your life with us!

    • Thanks Ali. I’m glad you liked the episode. It was tough being so open about my struggles, but it felt good to get it out ;o) I’m actually getting the itch to edit my clothes again (what a roller coaster ride)! I kept all my clothes when I was pregnant and was glad I did because I was able to get back to my pre-preggers weight w/in 2-4 months. So hang on…you’ll get there and those clothes will feel great again! Until then, if you desire that empty look, maybe store them away until you can wear them again…but definitely let them go if you didn’t like them before you got pregnant ;o) As for home pix, we’ve got a few of our home on our Pinterest page: that might help out. But we don’t have any of our bathrooms. We’ll try and fix that!!!

      • Thanks for the encouragement, Vanessa! Just to update, I bought two bins that fit under the bed. I filled them with clothes and now my closet can breathe again! Transition and change will definitely mark this season but I’m embracing it. Hope you guys have a great trip. I will definitely miss the podcasts but hope to visit the site more often!

  5. This episode was not only a lesson in the journey of living simply, it was a look into the inner workings of communication in a marriage. We often are at our very best at the beginning of the relationship and put our best attributes on display. After a few years, we settle in to our routines, appointed family duties and start the process of creating a family life. We often lose ourselves in the process and become frustrated, angry and disappointed at how our life is turning out.

    Dan and Vanessa in this great episode, decided to interview each other and address the feelings they had while completing their Project 333 clothes downsizing goal. The thoughtfulness, caring, listening and understanding that took place was something that every couple needs to listen to. This should be a weekly routine for all couples to play back to each other and really understand the dynamic of their relationship.

  6. As always, another great show! Thanks, guys for letting me be a fly on the wall. I really appreciate the follow-up on your wardrobe challenge and the honesty. I agree with Vanessa and what some of the other lady-commenters have said about clothes and body-image. This is one issue I still struggle with, and I could go on & on about how hard it is to set aside all the self-criticism, learning to accept my body with it’s imperfections and being thankful for it; yet, at the same time striving to be fitter, healthier & happier with myself. While I do not want to be too focused on appearances and concerns about what others think of me, I think we also need to acknowledge that how we present ourselves on the outside has a dramatic effect on the way others perceive us. I want my outside to accurately project who I am, while at the same time not putting too much emphasis on the external. It’s a balancing act, indeed!

    • Totally agree Michele! It’s a total balancing act because I too have tried to embrace the body I’ve been blessed with (and all it’s imperfections) but am very aware of the importance of appearances and others’ perceptions. You are so spot on! Thanks as always for sharing ;o)

  7. I have been doing P333 imperfectly for about 9 months (?) now, and Vanessa, I have some of the same issues as you. For the longest time I was intrigued by the challenge, but I couldn’t see any point in doing it – everything I had fit comfortably into my small closet, and I wore most of it regularly. Why would I store things away that were perfectly good, that I loved, that I could be wearing? At that point I felt I would rather just donate them (but I wasn’t at all ready to donate perfectly good clothes that I loved!). I have the same thing with feeling I am “wasting” things in drawers – I either want to use them or get rid of them. I don’t like storing things away.
    I started slowly by removing off-season things from my closet and storing those, and then I got used to a little more looseness in my closet (but not too much – I hate too much emptiness too! empty drawers drive me nuts!! I would have donated the dresser!). Then I worked on getting closer to 33, doing a little better each season.
    I have donated a lot of things, but I have also come to terms with having things in storage that I’m not ready to let go of but that I’m not wearing right now. I’m working on donating more and refining what I have. I track what I wear (and blog about it) and I have found that I don’t wear some things as often as I thought, even with only 33 things in the closet. It’s still a work in progress, but these last 2 months I have had 30-40 items in the closet and I’ve only had a couple of really bad days with nothing to wear. Which is about the same as before P333!
    btw I had a lot of strong emotions about storing things away and doing P333 even though I’m NOT very attached to clothing or image. It’s a funny thing. There was a lot of resistance and fear and anxiety, even though I wasn’t doing anything particularly drastic.
    Vanessa, have you considered having a 33-ish capsule for each of your major areas? 33 work clothes, 33 fitness wear, 33 casual/travel… something like that? I hope you keep working on it and find your sweet spot. Thanks for sharing your struggles. I think a lot of people have a similar experience. We talk about it a lot on the Dress With Less course page on Facebook.

    • I really like your idea of 33 capsule for different areas. It is a bit easier I think to figure out exactly what you need and you can tackle one area at a time.

  8. Wow! Thank you guys for putting this out there, what a great content. And Vanessa, I totally get it. I really do. Editing my clothes has been one of the harder areas for me to edit. My clothes (past and present) holds significant emotional value and symbolism, as I believe it does for most women. It’s an essential part of what makes me feel good. Just this year I finally donated the entire drawer full of jeans that fit me when I was 16/17 but haven’t since – I carried those around for well over a decade through multiple moves! It was ridiculous, I just couldn’t give up the hope that I would get that body back someday. While I always work towards bettering myself emotionally, physically and mentally, I really had to accept that I’ll never get that girls body back and that is okay. Hard stuff! Thank you again for such great content!

  9. I know you guys are kind of on hiatus, but I am re-listening to your podcasts and it is inspiring me to finally write some feedback. I am not sure if I was afraid to before or what but I am ready now.

    This episode was phenomenal. It was simple and honest and exactly EXACTLY how I feel about my clothes. Over the years (and I am only 29) I have fluctuated in weight and moved and changed careers… each time prompting a clothing purge followed by a completely new wardrobe. I have binged and purged so many times now I feel like my wardrobe is a little bit of everything great… ok a LOT a bit of everything great. “Simplicity you can have my junk food and my wallet and my toys and all my vices… but please please please don’t take my CLOTHES!” Just the thought of purging my clothes again made me anxious… brought up all the feelings and insecurities and misgivings that Vanessa expressed in this episode… I used the Carrie Bradshaw logic… some people have mortgages… I have a finely curated closet.

    But you guys… the thing is I wear a chef uniform to work five or six days a week. When I’m at work I am sweaty and gross and I feel like I look manly. I can’t wear jewellery or nail polish because of health codes and make up won’t stay on my face because of the heat. On my days off I like to dress up and feel like a girl. But do I need all of those clothes I bought when I was working at a University? Well I have fluctuated careers and needed those clothes again and had to shell out a bunch of money to buy new. It’s a mess. Back and forth. Justifying and deciding to simplify and then justifying again.

    Plus it is Canada up here… we have about 30 different seasons. Yesterday it was 17 degrees C out… (that’s like 55 F or something for you metric non-conformers) and today I had to scrape 6 inches of snow off my windshield. Is there a magic merino shants/tanktop/parka/waterproof onesie I can get? And does it look fabulous?… because I think at this point that’s all I want to wear. I am so fed up with trying to figure the whole thing out. Fashion as self-expression or consumption? Clothes that make you feel confident or comfortable? Sexy or practical? Too warm or too cold? Men can do anything in shorts and a t-shirt and a good casual shoe. I have to plan shoes in advance, how much walking, standing, dancing are we going to do? It’s EXHAUSTING.

    Thank you Vanessa for sharing your feelings. I had simplifier guilt over my closet big time. It was wasteful and ridiculous. I have a small house, about 800 square feet and my bedroom closet is very small. Most of my wardrobe is stored in a walk in closet in the attic. How perfect then was this episode for me? Store your clothes in the attic you said. Bring down what you will wear for the time being you said. A light bulb went off. I am always leaving the items that need to go upstairs in a laundry basket at the end of my bed. I hate going up there to get dressed in the morning, so I just end up wearing the much more casual clothes that I store in the bedroom dresser. This means that I don’t even get to experience that girly feeling that I was talking about on my days off because I usually just throw on a hoody, some jeans and a ball cap and go about my day. Doing the 33 item, or whatever amount of items works for you, wardrobe in my bedroom and leaving the rest of the items upstairs will allow me to SLOWLY purge things at a rate that I am comfortable with. I have done the capsule wardrobe thing before, packing 30 items for 6 months in Europe, so this should be much less complicated… and I think I will switch things out monthly to make sure I have what I need for our insane weather. But I just wanted to reach out and thank you so very much for helping me with this life long conundrum. This experience was like a microcosm of every little thing I ever learned from the show and from my simplicity journey in general.

    You organized my space, helped me come up with a system that I think will work for me, pointed out the flaws in my current system, reminded me of my goals and my simplicity mission, and provided support through the whole process with your candid honesty. All without even knowing it.

    On another note, the quality of this show was fantastic… the authenticity, emotion, and off the cuff chatting really made the episode feel very intimate and cozy. Could this be a way to take some of the pressure off producing content for the show? Don’t be afraid that what you say is not meaningful enough, or researched enough, or prepared enough. Your genuine selves are great just as they are.

    I am sad you guys are not around on the regular anymore, however I completely understand why. I don’t know why it has taken me so long to thank you for all you have done, but please accept my gratitude now. Apologies for the novel… Angie

    • Thank you so much, Angie! We’re glad this episode meant so much to you. It did to us, too. I mentioned in another comment you sent that something broke in our comment notification system and I haven’t been getting notifications when people post. I’m so sorry it has taken so long to reply.I’ll have to have Vanessa pop in here too to address some of your concerns. It sounds like you two were having some of the same feelings about limiting your wardrobe too much.

      You say you’ll be sad we’re not around on the regular basis anymore…but don’t worry Angie. It’s comments like yours that keep us coming back!!!

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