Should You Buy Non-Flattering Clothes?

This is NOT a trick question

Please note: this post discusses potentially sensitive topics related to body image and looks - I am trying to be honest and share my experience and thoughts with you, but if this is not your cup of tea, please feel free to skip!

A few months ago, I hit a style block. It started when I accidentally lost 10 pounds due to a medical issue, then gained it back within a couple of months. As I lost weight, dressing became easier. I could use my waist to create new proportions, and many of my pieces looked much better (ugh, I hate to even write this!). Once the weight came back, dressing became harder, which upset me, as I fervently believe you can look good with any body type. Over three months, I went through a rollercoaster from “some things look good on me,” to “many things look good on me,” to “some things look good on me” again.

Since then, I’ve been thinking more about “flattering” clothes. Recently, it has become a bit of a taboo word as flattering became synonymous with “slimming.” For this post, I consider flattering in a broader sense - does the shape, color, and quality of the piece make you look good (which is of course subjective and personal)? Some clothes can be very flattering but not match your personality and style, and vice versa. Note, I am not considering ill-fitting clothes here - the clothes in this post must fit well.

So should we choose clothes that are flattering? Should we ignore that and only care about the style and what the clothes communicate about us? Here is a review from my recent try-ons to answer these questions.

Flattering & my style: an obvious case

This category is a no-brainer. These pieces make the most of both worlds and are what we all are drawn to. The silk blazer in this photo from Cos looks stunning on me and is also my style, which is the perfect formula for a favorite piece.

Flattering & not my style: beware, beware, beware!

This category is the trickiest of all. I believe this is where many style mistakes happen. I once spoke with a woman wearing a size that is not always available in designer fashion, and she said she does not buy designer pieces, as she only picks the few pieces that are flattering on her and then never wears them. I find that only 15-25% of clothes I try on look good on me. Once you find those, it feels like such a catch - but I need to think if a stunning piece truly fits my style, as otherwise, I won’t wear it and will struggle to make it work in my wardrobe.

For example, this yellow or black cardigan from Cos looks stunning on me (in my view anyway). I was drawn to it and loved its shape on me. However, it feels a little conservative for me. It is sheer but wool (so unclear what to wear underneath), and the neckline is too low for practicality. I know if I bought it, I would struggle to wear it, and I’m glad I didn’t succumb.

I did succumb to the pink jacket below because it looked good on me, but I spent more time fixing it than wearing it. I wanted a short jacket that looked good, and it did - but nothing else was right about it. It’s too conservative, too cute, too prissy. I changed buttons, removed embellishments, and still have worn it only twice or thrice. “Flattering” can be deceiving, as even the most flattering piece is hard to wear if it’s not who you are.

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Non-flattering & my style: it’s personal