How to Stop Second-Guessing Your Style Purchases (And Give Yourself Permission to Buy the Good Stuff)
Have you ever stood in a store, holding something beautiful, but put it back because it felt too expensive or too risky?
Michelle did. In fact, she wrote in with a question I hear all the time:
“I have trouble giving myself permission to purchase more expensive items that, in the long run, I’ll love and use more than the cheap stuff. How can I overcome this?”
You are not alone.
Here’s the truth: many of us have made expensive wardrobe mistakes in the past—and we’re now trying to avoid making more. That fear? It’s not irrational. Research shows we only wear around 10–20% of what’s in our wardrobes. The rest is money sitting idle on hangers. This makes you feel guilty and wasteful. You don’t want to make the same mistake again
So, of course, we hesitate. We’re trying to protect ourselves.
But here’s the problem: if you keep avoiding investment-level purchases because you’re afraid to get it wrong, you end up with a closet full of “safe” pieces… that you don’t actually wear or love.
So how do you know what’s truly worth spending on?
You need your own personal style criteria.
Not a list from a fashion magazine. Not a trend report. Your own system based on your body, your lifestyle, your colouring, your personality, and your values.
Because when you know what works for you, decision-making becomes so much easier. Instead of standing in the fitting room debating, you can ask yourself:
✔ Does this meet my style criteria and style recipe?
✔ Does this fill a genuine gap in my wardrobe?
✔ Does it align with how I want to feel and show up?
✔ Does it work for my current lifestyle? Not an imaginary lifestyle or your previous lifestyle.
And if the answer is yes? That purchase is no longer a gamble. It’s a smart investment.
My First Scary-Spendy Purchase
I still remember the first time I bought something full price—and over $150. It was decades ago, and at the time, it felt terrifying.
But here’s why I bought it:
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It was in a colour I wore all the time.
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It paired easily with multiple things I already owned.
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I could dress it up or down.
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It felt like me , not just “on trend.”
That piece ticked every one of my boxes. And do you know what happened?
I wore it to death. I probably wore that top 500 times before the fabric expired. I had it for over a decade (it was a classic style, so it didn’t date).
It was one of those rare pieces that earned its keep ten times over. The cost per wear was so low, it practically paid me to wear it. Because it fit me. My style. My life. My personality.
That’s what I want for you.
Why Spending More Can Mean Saving Money
A cheap garment made from a poor-quality fabric won’t last. Petroleum-based plastic fabrics (acrylic, polyester, nylon, polar fleece, we’re looking at you) pill and wear quickly and just don’t last. They may be cheap, but you have to replace them much more quickly.
This top is one I still have and wear – it’s made from quality cotton and doesn’t look in the least bit old, and because it’s a creative shape, it’s not in fashion, so it hasn’t gone out of fashion. This photo was taken a decade ago and is from a brand (Metalicus) that has sadly gone out of business (2018).
Compare that with high-quality merino wool, silk, cotton, or linen, and you’ll find that the garments wear well for years, so their cost per wear decreases. I bought a gorgeous red merino cardigan back in 1999; it never pilled because high-quality, well-spun merino wool has very few ends, which are the bits that end up pilling, and I wore it frequently for over a decade (or longer) before I finally wore holes in it. Today, I’d be mending it with visible mending if I still had it, using sashiko and boro – the Japanese art of visible mending, where the concept of Kintsugi holds that the imperfection lies in the beauty and value.
I own leather knee-high boots that I’ve worn winter after winter for decades. And as my colouring has changed, I have kept them (I’ve worn them in and they are comfortable) and painted them a new colour. Yes, they were an investment to buy, but they last and can be improved with boot polish. Contrast that to “vegan leather” which once scratched can’t be fixed and end up looking scuffed quickly and need to be replaced. That’s not economical.
The brown boots in the picture above I still own and have painted to a cobalt blue (below).
Buying cheap low quality clothes means that not only are the people who make the clothes being exploited (because if you’re buying a garment and it has to be imported from across the world, them warehoused, delivered to stores that have to pay rent, and sold by sales assistants who also get paid, as well as the company wanting to turn a profit, and able to pay all it’s admin and management employees, how much of that purchase prices is the worker who made it being paid?), plus most likely the there is a high environmental cost for the production of the fabric as well as.
It’s better to save up money and buy one great quality item that you really love and that works for you than buy lots of “it’ll do” pieces that you end up not wearing (landfill, being burnt, or shipped to a beach in Chile or Africa) is probably not in alignment with your values. Once you have enough clothes to be “not naked”, it’s better to start saving up for fewer, higher-quality pieces than buying more cheap items. Plus high quality doesn’t always come at a high price, consider second-hand, consignment and thrift shopping as well as clothing swaps as alternatives to heading to the mall.
Why Style Education Changes Everything
When you understand colour theory, body shape, style lines, personality expression, and lifestyle alignment, you stop guessing. You stop hoping that maybe this time, it’ll be the right thing.
Obtaining an education is an investment that pays itself back many times over. You have to keep buying clothes for the rest of your life, knowing which pieces to buy and knowing that they are going to be valuable additions (or replacements) for your wardrobe means that you feel good spending the money.
You know.
That’s exactly why I created my 7 Steps to Style program. It’s designed to give you the tools you never got at school—or from fashion magazines.
You’ll learn how to build a wardrobe that:
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Makes sense for your life
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Reflects who you are today (not who you used to be)
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Supports your confidence and comfort
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Is full of pieces you actually wear
Because let’s be honest: we spend a lot on clothes over our lifetime. Recent figures suggest the average person spends between $150,000 and $500,000 on clothing and apparel, and currently the global women’s apparel market is worth $1.05 TRILLION. And yet? So many women still feel like they have “nothing to wear.”
It’s not a spending problem. It’s an information gap.
What’s Really Holding You Back?
Sometimes, it’s not just the fear of making a mistake—it’s the stories we’ve picked up about money and self-worth.
Perhaps you grew up believing that spending money on clothes is a frivolous expense. Or that caring about how you dress is vain. Or that it’s shallow to want to look good.
But let’s flip that on its head for a moment.
You have to wear clothes. (Society demands it, unless you fancy being arrested!) So, isn’t it worth investing in pieces that support your confidence, comfort, and self-expression?
In fact, science supports this. There’s a growing body of research in psychology that shows what we wear influences not just how others perceive us, but how we behave, feel, and think. This is known as “enclothed cognition.”
Colour, in particular, affects our mood and emotional state. A recent meta-analysis reviewing 132 studies spanning over a century showed that we have consistent emotional reactions to certain colours. So yes—what you wear does matter.
It’s not shallow. It’s smart psychology.
Style Isn’t About Rules. It’s About You
When you have your personalised style criteria, shopping becomes more like meal planning.
Imagine going to the supermarket with a clear menu for the week and a list of ingredients. You’re not wandering aimlessly down the aisles hoping inspiration will strike. You know what you need. You buy it. Done.
That’s what a great wardrobe system does for you.
So next time you find yourself eyeing that “a bit expensive” piece and wondering if it’s worth it—ask yourself:
- Is this a colour I love and wear often that makes me look great?
- Does it work with my existing wardrobe and can I wear it with multiple garments I already own?
- Will I wear it at least 100 times?
- Does it suit my lifestyle today?
- Does it express who I am?
If the answer is yes… give yourself permission.
Because when your wardrobe is full of clothing that reflects your values, supports your body, and simplifies your life, getting dressed becomes joyful again.
And you? You become one of those rare women who actually wear 80% of her wardrobe with confidence and ease.
Want that kind of wardrobe clarity?
That’s exactly what we do inside the 7 Steps to Style.
Because you don’t need more stuff—you need the right stuff for you.
The 7 Steps to Style program gives you the tools to understand exactly what works for you—so you can build a wardrobe you actually wear and love.
✨ No more guesswork. Just clarity, confidence, and clothes that feel like you.
