I see it all the time, people spending big on a garment that they will only wear once, maybe twice. An incredible waste of money in my opinion...
I'm all about wearing the items you invest in, and dressing for however you want to feel that day. With the way I structure and declutter my wardrobe it doesn't make sense for me to wear expensive and/or statement pieces only on rare occasions. The way that I see it is that better quality clothes should be worn more often. If they are of a higher production standard they are going to last you longer, and you'll just end up treating them better anyway.
The amount of care and attention to detail I give my more expensive wardrobe pieces may seem a little funny to some. I am quite particular about how I do my laundry, and, if on the odd chance there is a small amount of damage to the garment I will either fix it myself, or take it to someone to be fixed if it's outside of my skill level.
It can take a long time and constant self-coaching to overcome the opinions of others too, especially if you weren't already that way inclined. As long as you feel confident and happy in front of the mirror, eventually you will be able to drag that feeling out into the wild with you, it may just take a little practise at first, but stand tall, breathe, and tell yourself you've got this.
There's nothing wrong with being a little overdressed, and nothing wrong with wearing something 'weird'. Invest in clothing that you'll feel proud to have hanging up on a rack, you should love it enough that you have it out on display all the time! There's nothing wrong with feeling happy with the things you do own, in fact if they're able to bring you happiness then I think that's great. The problem arises when there's the obsession with constantly needing new things to fill some kind of void, you see a sale or just end up on a fast fashion website and start adding to cart. Let's avoid that!
Here are some questions to ask yourself next time you're adding something new to your wardrobe:
1. What else do I own that I can wear this with?
2. Does it fit my existing colour and pattern scheme?
3. Where can I wear this?
4. Does it fit me well?
5. Is it well-made? (see this video for tips)
6. How many times can I see myself wearing this in the next month?
8. Do I feel good wearing it?