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This Was My Number One Wardrobe Mistake … [Episode 31]

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One thing stands out when I reflect on my wardrobe struggles: a fundamental flaw in how I approached fashion. It left me constantly searching for that “missing piece”, that elusive purchase that would (hopefully) pull my wardrobe together and leave me feeling well-dressed and confident. But I can see now that I was going about it the wrong way, and I explain it all in this episode of The Simply + Fiercely Show.

In This Episode:

  • The simple yet fundamental mindset shift that changed my wardrobe for good
  • Why buying something new rarely solves your outfit dilemmas
  • How to stop reinventing the wheel when it comes to getting dressed

Featured In This Episode:

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Note: this is not an exact transcript and has been edited for clarity.

This Was My Number One Wardrobe Mistake

Hello, everybody, it’s Jen here and this is another episode of Simply and Fiercely Show. 

Today I’m back talking more about minimalist wardrobes, our closets, and my approach to fashion and getting dressed in general. 

Before I dive into the topic of today’s episode, which is sharing the number one wardrobe mistake that I made for years, I just want to explain why I’m so passionate about this topic. 

I am someone who honestly when I think about my life, I probably spent close to 30 years feeling consumed by clothes. Part of me is kind of embarrassed to say that because it feels a little bit shameful. 

It’s one of those things where I feel like you can’t win as a woman.

If you don’t look put together, people judge you. But then at the same time, you’re also not supposed to care because if you care too much, then you are materialistic or vain. 

So it’s this weird spot a lot of us find ourselves in when it comes to getting dressed. 

When I think about my own life, the stress and the overwhelm that I felt around getting dressed, shopping, decluttering, etc. It consumed a massive part of my life in terms of physical space, how big my closet was, and money.

Oh my goodness, I don’t even think I could share in the podcast right now, how much money I’ve wasted on clothes over the years. Probably enough to buy a house if I’m honest with you. 

I’ve wasted so much space, so much money, so much time that I’ve spent shopping, or even just thinking about what to wear. 

I think I’ve read this statistic recently that said that women spend an average of something like 16 minutes a day deciding what to wear. I totally believe it.

I have done a lot to simplify my wardrobe, and we’re going to talk about that more in this episode, but there was a time when I spent at least a half-hour a day trying to figure out what to wear, trying on different outfits, etc. 

And I want to say that it’s more than that, too. There’s also the mental stress, as you go through your day if you don’t feel confident in your outfit.

I’m not sure if it’s just me, or if you’ve experienced it as well, but when you get dressed, and you’re not comfortable in what you’re wearing and you’re pulling at your clothes throughout the day. If they’re physically uncomfortable it adds to your mental load.

Where you catch your reflection and you’re like, ‘Oh, God’ and there’s this whole ecosystem of stress and overwhelm. 

There are some people where fashion and getting dressed is a form of self expression and they love it in the same way someone might love painting.

It’s like a creative artistic outlet for them. And that’s totally fine. There’s no judgment against that. 

But I do think that for a lot of women, that’s not the case. What they want is to be able to get dressed easily and effortlessly without having to spend so much time and energy. 

If you fall into that second camp, then this episode is really for you. 

I want to share, as I said, this big mistake that I was making. And I don’t think I’m alone. I think that there are a lot of other women out there who are struggling with the same thing. 

Wardrobe goal – to feel comfortable and confident in clothes

Let’s get straight to the point. 

The number one mistake that I was making was the way I was thinking about my wardrobe goals.

I know that sounds a bit bizarre so let me break it down for you.

I thought that my goal in getting dressed was to look cute and fashionable.

Maybe you don’t think cute. Maybe you think stylish or, you know what I mean? There are different words that you can use. 

But I thought that my goal had to do with my outward appearance. I wanted people to look at me and think that my outfits looked good. 

Fashion was the goal. But when I really thought about it, I found that that’s not actually true.

My real goal is to feel comfortable and confident in my clothes.

When I walk into a room, I want to feel physically comfortable in my clothes. I want to get dressed in the morning, and then not think about my outfit for the rest of the day.

Being fashionable was just the vessel that I thought would help me achieve those goals.

The real goal behind the goal is to achieve how you want to live your life at the present

If that is a little bit hard to get your head around, let me use a different example. 

I have a program called Values and Vision that I teach once a year, it’s closed at the moment. I will be teaching it around May again this year. 

But one of the things we talk about there is really figuring out your vision for your life.

What matters to you? What is the goal that you want? How do you want to live your life? 

When I am teaching this course, one example that I always use, is a lot of people think that their goal or their vision, what they want to achieve, is something you’ll check off your checklist in the future. 

So for example, let’s say that you want to retire one day, and buy a beach house. That sounds like a reasonable goal or something to be working towards. 

But what I tell people, is that you think the beach house is your goal, but what you really want is the lifestyle that you imagine you’re going to have, when you have that beach house. The beach house is just the vessel. 

You might imagine that when you’re living in this beach house you’re going to feel more relaxed, you’re going to be more present, you’re going to spend more time in nature, have more time for yourself, more time for your loved ones, you’re going to sit down on the back deck and you know, just appreciate life. 

You have this vision and it could be different for everyone. 

But you have in your brain, this image of how you imagine you’re going to be living when you get that beach house. 

The beach house is like a physical manifestation of that, a placeholder. 

In theory, you could be living that same life in lots of different places, but you like the beach so that’s how you envision it. I hope I’m making sense. 

So what happens when you have that kind of mentality is that you think, ‘Oh, I can’t be happy until I have the beach house’. 

But when you realize the goal behind the goal, sometimes the way that we phrase it is actually to say be present, to get out in nature more, etc. 

You can start doing that now. You can start living your life in that way, basically living the future that you want, even if you don’t have the beach house. 

Finding comfort and confidence through wardrobe analysis

Driving the point back around to wardrobes, it’s the same with clothes.

Unless you are someone who really enjoys fashion, for the sake of fashion, when we say we want to look stylish, we don’t actually care about looking stylish, per se. 

What we care about is how we think we’re going to feel when we look stylish. 

When you think about that, you think, ‘Oh, if I’m looking stylish then I’m going feel really confident’. 

I’m going to feel comfortable, I’m not going to have to think about my wardrobe, or how I get dressed. 

I’m just going to walk into a room and feel good in my skin.

When you think about that goal, think about the way that you are currently trying to achieve that goal. Think about the way that you’re currently getting dressed. 

So again, for me, what I was always doing was things like reading Vogue, going through magazines, or looking for ways to elevate my outfits or ways to better style my outfits.

I was always looking for something more, something new, and it was like I thought if I could find this missing piece of the puzzle, all of a sudden all my problems would be solved.

I just had to find a new style. Sometimes I would think that buying something new would fix it.

I would feel so frumpy and think that my closet was such a mess, but I was so sure that if I just bought those new shoes, it would bring everything together and suddenly I would feel stylish.

Or if I just had that classic blazer, whatever it is that the magazine was telling me that was the must have for the season then all my clothes would suddenly be spruced up. Then I would feel so comfortable and stylish and confident in my clothes. 

If you go back to the idea that your real goal is to feel comfortable and confident, you can see why this doesn’t necessarily work. 

I don’t know about you, but when I feel confident, it’s not usually because I’m constantly trying to be someone I’m not or constantly experimenting with completely new things. 

It usually happens when I find out more about myself and then look at how I can be more authentically myself. 

For example, when I think about my wardrobe, and this is the exact process that I went through over the years, I stopped looking at magazines completely. 

I stopped focusing on what’s in the shops and what the trends are right now. Instead, I started looking at my closet more closely.

By looking at my clothes and asking myself, okay, what is it that I already own that makes me feel comfortable and confident? 

The best kind of mental trick I use, when I’m asking myself these questions, and what I recommend you do this as well, is that imagine that it’s laundry day, and absolutely everything that you own is clean and in your closet.

My guess is that there are a few things that you instinctively reach for.

So everything’s clean and you can wear anything you own. There are a few go-to pieces that you really enjoy putting on and you don’t overthink things, right? 

Where things get kind of difficult is when they’re in the wash. Then you’re trying to put together outfits and it requires a bit more effort. 

You know that whole saying that women only wear 20% of their wardrobe.

And that’s probably because you’ve got a few pieces that you love and the rest of it you might admire on the hanger, but you don’t feel good wearing it.

We talked about that a bit more in the previous episode, 3 Things That Took My Closet From A Cluttered Mess To Streamlined And Functional, if you want to check that out. 

Going back to this whole concept of mining your wardrobe for what already feels good and then doing more of what feels good, for me was the secret to feeling comfortable and confident in my clothes.

That might not necessarily be the thing that makes you feel like the biggest fashionista. You’re not going to be the trendiest person in the room, you might not be, you know, stopped to the street. 

But it doesn’t matter. Because when you are constantly putting on clothes that make you feel good, the things that make you feel most like yourself, then you achieve your wardrobe goal.

And if I bring us back to where I was making a mistake, that was my mistake. 

I thought that the thing that was going to make me feel best was being “as stylish” as possible, whatever that even means.

Where the thing that makes me feel my best is wearing the clothes that I know I love over and over again. Even as the years passed, even as styles changed, even as what the magazine says is in.

What do they say now? That skinny jeans are out? 

On a side tangent, I tried to sell some skinny jeans at this very trendy consignment shop and the woman looked at me in horror, because apparently, they do not take skinny jeans. Nobody wants them. 

So anyway, my point is that I no longer let fashion or what’s in style define me. Instead, I have a wardrobe that I love.

When I want to experiment with new things or when I’m shopping, I’m evaluating how everything is going to work with the wardrobe that I have and that I love. 

That is the heart of things. 

I can add to it or I could do little tweaks to it but I’m never at a point where I’m reinventing the wheel. 

When we talk about this whole idea where women are spending 16 minutes a day, or however long, getting dressed. It’s because there’s this pressure to be constantly reinventing the wheel.

There’s this idea that if you want to be stylish, you have to be always changing. And always changing requires a lot of mental work. 

Jen’s personal uniform method in building a wardrobe for confidence and simplicity

And so, as I said, I think that you get that confidence out of knowing something is tried and tested. Knowing that you’re wearing an outfit that feels good. 

Honestly, I cannot remember the last time that I spent more than like two minutes thinking about what I was going to wear. I love everything in my closet and I know exactly how to style it. 

It’s really based more on a mood or the weather. How my body feels or whatever that day when I’m picking out what to wear. But it’s never a puzzle. 

I’m never sitting there, thinking, ‘How can I put together an outfit.’ 

The framework that made this happen is my personal uniform method. 

If you are listening to this and the word personal uniform makes you want to vomit or run away because it sounds really boring. Please know that the way that I define a personal uniform, or the way that I make it work for myself, is not about wearing the exact same thing every day. 

I do repeat a lot of outfits, but I still feel like there’s enough variety that there’s room for some creativity and flexibility.

There’s a rhythm and a framework to how I get dressed, it’s changed everything for me. 

I am 42 and I have almost the least amount of clothes I’ve ever had. The least amount of clothes that I’ve ever had would probably be during a time before I had kids. I was much more of an extreme minimalist. But I still have a pretty small wardrobe now.

On top of that,  just to share something a little personal, I am the heaviest I have ever been in my life, by far. 

And yet even with my age, my weight, I’ve had two kids and my body has changed, I have never felt as comfortable or confident in myself as I do now.

I feel really good, I’m not saying that I am a fashionista. I’m not saying that I’m always going to be the most fashionable person in the room. But no matter what I wear, I feel confident and I’m comfortable. I feel so good in my clothes. 

That’s why I’m so passionate about this. I feel like there’s a whole industry designed to make us uncomfortable in our clothes so that we keep spending. 

It’s like a conspiracy where we are spending so much money, so much time, so much energy in this cycle of thinking about what to wear and how to get dressed. 

It is so freeing to break free from that.

Invitation to a live workshop happening on November 5, 2023, at 7 pm Eastern time

I’ve created a system that allows you to care about fashion and to want to have style, but to have it be effortless. 

If you are interested in learning my framework and how I make this happen, I am teaching a live workshop on the fifth of November, 2023 at 7 pm Eastern time. 

Just to be clear, I’m not a stylist, and I’m not going to teach you things like how to dress your body shape. I reject the idea that only certain people can wear certain things anyway. 

What I will teach you is a method that is about mining your current wardrobe for data, so that we can figure out exactly what it is that helps you achieve your wardrobe goal to be comfortable and confident.

Then we use that information to create flexible formulas for getting dressed, aka your personal uniform. 

Again, this doesn’t mean that you have to wear the exact same thing every day. 

It doesn’t mean that you can’t ever try new trends or that your style can evolve, but what it does do is give you a framework. 

This framework makes shopping easier, it makes getting dressed easier. It helps you evaluate new styles and new trends to figure out, ‘Okay, that one’s going to work for me or that one is not right’.

Then you can upgrade your wardrobe when you want to, without wasting your money buying tons of clothes that you’re just going to declutter in 12 months.

Because as much as I am into decluttering and I believe that it’s okay to declutter, it’s okay that we all have clutter, sometimes in our lives. You’re never really done decluttering. 

But at the same time, I don’t want you to be stuck in a constant cycle where you’re constantly buying things and then decluttering and buying things and then decluttering it, etc. You want to slow that cycle down.

This is the exact system that I used for myself to build my wardrobe. It’s how I evaluate clothes when I’m in a shop, even when I look through a magazine. 

Because I have my personal uniform, I can look through it and I can tell exactly which styles I might want to try for myself and which ones aren’t going to be suitable. I have so much clarity. 

For those who are familiar with my work, I believe that anytime you’re trying to simplify something, whether it’s your closet, your schedule, your home, etc. it all starts with clarity. 

If you are interested in learning more, as I mentioned, I am teaching this live on the fifth of November 2023, and then it will only be available inside my program, the One Day Closet Cleanse. 

Not because I want to gatekeep information from you. It’s because I teach a lot in that program about obviously how to declutter your closet but there’s also an entire module about shopping. 

It’s a live workshop that I taught earlier this year about why we buy clothes that we never wear. 

It’s all of these pieces working together. 

You need to be able to declutter, you need to be able to make more intentional decisions when you’re shopping. And then you need to know how to put together outfits in a way that’s going to make you feel good.

They all go hand in hand so I think that teaching the uniform workshop without the rest of the program would be doing you a disservice. 

So this is sort of like a one-stop shop, everything that I know about closets and wardrobes, and how to save you money, save you time, save you energy, make you feel good in your clothes. 

Again, the workshop is on the fifth of November, 2023. If you are listening to this, and it’s after the fifth of November, don’t worry, it’s going to be recorded, and then it will live inside of the program so if you buy The One Day Closet Cleanse, you still get access to it.

Thanks for listening. Until next week. Take care.

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