I am extremely grateful for my wardrobe, and in a very happy place with my style. I love my stuff, look forward to putting on a-fab-for-me outfit each morning, and seldom make shopping mistakes these days. But, I’ve made loads of shopping mistakes in the past, and I learned from them the hard way. 

1. Committing to Uncomfortable Footwear

I have wasted an embarrassing amount of money on footwear that looked great, but was uncomfortable. Over and over again I was stubborn about believing that uncomfortable and ill-fitting shoes would become comfortable over time, and mould to my feet. Well, they didn’t. Either I ended up with sore feet, or shoes that were seldom worn. I finally realized that there is only so much that I can do to make shoes comfy with insoles and anti-chafing balm. Slowly but surely, I’ve learned which types of shoes are suited to my feet and walking lifestyle, and which are not. I still make footwear shopping mistakes, but far, far less frequently.

If the types of shoes I wear are having their fashion moment, bonus. If not, it’s all good. Go Team Happy Feet.

2. Shopping for an Imaginary Climate

I thoroughly enjoy wearing and shopping for Spring and Summer fashion. It’s my favourite. But I no longer live in a tropical or Mediterranean climate, so I don’t need as much of it as I used to. When I first moved to Seattle eighteen years ago, I continued to shop for my favourite seasons instead of my dominant seasons. Since I loathe to feel cold, this led to a wardrobe of gorgeous items that I seldom wore. It took me years of living here to get this part of my shopping strategy right.

I’m the one wrapped up and covered when others are not. I’m the one in trousers, a pullover, and jacket for dressy occasions when others are in sleeveless dresses. I’m the one in closed footwear when others are in sandals. I finally have a wardrobe that reflects my need to feel insulated, and it’s awesome.

3. Wearing a Look Meant for Someone Else

For years, especially early in my retail buying days, I bought items that I thought I should be wearing because I was a fashion professional. They were usually hard-edged items, lots of black, and avant-garde silhouettes. Beautiful pieces that are meant for some of our forum members, my clients, and my friends, but not for me. It took me years to acknowledge that these items do not make me happy, and I shouldn’t wear them.

I enjoy wearing playful, crisp, retro, “soft and pretty”, trendy classic looks that are on the dressy side, and with lots of colour and pattern. That is what I embraced after soul searching and being honest with myself about what I truly enjoy wearing, instead of what I thought I should be wearing. Go Team SIMPAT Style.

It doesn’t matter if what you enjoy wearing is not worn by fashion influencers, your peers, or on-trend. What matters is that you like your outfits, feel good in them, and can get on with your day.

Over to you. Do these shopping mistakes resonate with you? Feel free to share your own recurring shopping mistakes in the comments, and hopefully you’re learning from them too.