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You’ve seen the articles answering questions like … “What should I stop wearing after 25?” or “What should stop wearing in my 40s or 50s?” or “Should a 70 year old woman wear leggings?” or “How should I dress according to my age?” Ugh! We are asking and answering the wrong questions. If we continue down that path we will forever be looking for external validation, seeking happiness and fulfillment outside of ourselves. It never satisfies so we have to keep seeking and seeking.
I’m not interested in offering you fashion tips or weighing in on the latest fashion trend (though I do have the perfect outfit recommendation at the end of this article). I genuinely don’t care about those things. If you want to wear skinny jeans or boyfriend jeans, scarves or belts, navy jackets, tennis shoes or other footwear, black, beige, nude, stripes, textures, or whatever silhouettes you are comfortable in, I’m happy for you. You can even put glitter in your hair and I will support that. You may have a classic style or minimalist style or have no idea what your personal style is. It’s all ok.
Spoiler Alert: You can (and should) wear whatever clothing you want.
The truth is you can wear anything you want at any age. So now that you aren’t mad at me for telling you what to keep in your closet or telling you that you have to dress any kind of way, I hope you’ll enjoy my recommendations for what not to wear in your life. I’ve learned so much from and . While I’ve learned what best fits my body and my lifestyle, most of the lessons have nothing to do with clothing.
I typically steer away from making recommendations on what you should wear, but feel strongly that none of us (at any age) need to wear the following three things ever again. Don’t worry, I’m not coming for your jeans, leggings, comfort clothes or anything else you love to wear. Instead, I want to give you permission to feel lighter and to enjoy your life more by refusing to wear these three things we’ve all dressed in before. It may not come naturally, and will require some practice but it will get easier and easier to remove these things from your life.
Please Stop Wearing These 3 Things (at any age)
These things to stop wearing (as you’ve probably guessed) aren’t external things we wear like makeup, jewelry, a t-shirt, trousers or ties but instead, I’m talking about things we wear on the inside. That’s where the heavy stuff usually lies. If we could let these things go, stop wearing them on our sleeves and our hearts, what would we have the energy, clarity and time for? What could we create or appreciate? How would our lives change if we simply said, enough is enough when it comes to these three things.
1. Stop wearing the guilt of your past.
Guilt and regret remove us from our lives. We feel unhappy and we struggle to reconnect with the present moments and simple pleasures that are right in front of us. You might feel guilty when you don’t feel like you got enough done, or when you have to say no or set a boundary with someone you love. You may even feel guilty when you get sick and have to take time off to rest. People tell me they feel guilty for relaxing and doing nothing or not attending an event they don’t want to attend. If you can relate and have felt guilty for these things, I’d like to suggest that you aren’t feeling guilty. Instead, you are feeling discomfort for taking care of yourself.
Let go, apologize, forgive and choose to live free of guilt and regret. As they say, life is too short. We can’t spend our time stressing over things that have already happened. Learn what lessons the past offered you and then release what came before so you can be present for your life today.
2. Stop wearing the pressure to prove yourself.
I rarely bought clothes, accessories, skirts or boots because I actually needed more clothes. I had plenty. Instead I purchased clothing to feel a certain way and to be perceived a certain way … to prove myself. I wanted to feel smart, beautiful and loved. I wanted other people to think I was those things too. I tried to prove who I was by what I wore and by what I accomplished. I was always measuring myself by how much I got done. Check marks on my to-do list were a measuring system that failed me over and over again. The problem was that there was always more to do and more to prove and eventually I forgot who I was in the process.
Over time I decided to, and instead of what I thought might be important to everyone else. If you have to prove yourself to people you love, that isn’t love. If you struggle to prove yourself at work, maybe you aren’t doing the right work. If you don’t believe me, just stop for a while. Stop pushing and proving and wishing that people would see you the way you think you need to be seen to succeed. Instead, let them see you for you. Once you stop proving yourself, you can be yourself.
3. Stop wearing the weight of other people’s expectations and judgements.
Society wants to tell us what to wear (inside and out) whether we are teenagers, middle aged or senior women and I finally reject all of it. One of the most astounding realizations I made in the first three months of Project 333, the minimalist fashion challenge that invites you to dress with 33 items or less, is that no one really cared what I was wearing. No one even noticed! Once I figured that out, I wondered why was I trying to please anyone with my clothing choices or my life choices.
Caring less about what other people think is the ultimate form of self-care. Usually, when we think people are thinking about us, they aren’t. And when they are, their thoughts are more about them, or their mood or their point of view. What would you do if you cared a little bit less about what they thought, what their expectations were, and who you thought you were supposed to be for everyone else?
Giving myself permission to let go of my need to meet other people’s or to feel any kind of way based on judgements (good or bad) helps me to trust myself and allows me to love my life regardless of outside feedback. I’m not good or bad or right or wrong because of what anyone else thinks. I and I’m not going to change myself trying. When you stop wearing the weight of other people’s expectations and judgements, you’ll be light. Wearing these things is wearing you down. You can stop now. Please stop. Wear the clothes you want to wear. Live the life you want live. Be you.
But what outfit should you wear?
I’ve been pretty clear about the things to stop wearing and you might might be wondering what you should wear. It may take some time to figure it out as you break free of the expectations of others and forgive yourself for past mistakes. I wrote a book called Gentle, Rest More, Stress Less, and Live the Life You Actually Want (coming out in February 2025) and many of the practices in the book reflect the lessons in this article.
It’s so important for us to embrace the agency we have over our own lives, to begin to prioritze our own well-being and to wear what makes us feel best. The outfit I suggest you wear as you decide what is best for you is curiosity, pared with gentleness, love and of course, a little glitter. If you want more support, join the free Tiny Step Simplicity Challenge starting August 18th.
