Most people are uncomfortable with all three of these statements, but let’s focus on the last one for now: wear more often.
I’ve noticed that people feel that if they were photographed in something and it appears on social media, they don't want to wear it again. Can you wear something again if it’s been in a photo on Facebook? Or maybe you're worried that people will notice you're wearing the same thing every week.
Here's my response to all of that: first of all, people won't notice - everyone else is as worried about theirselves and consumed with their own thoughts as you are. Second of all, if they do, their problem - they should find something more important to be concerned about. Third: if you buy more simple and neutral clothing, workhorses, it'll be less noticeable.
This last point can be really helpful.
If you wear a pink sequined jumpsuit twice a week, that might not go unnoticed. But what if you often wear a white tee and jeans? Doubt anyone's going to notice, especially when you pair them with a scarf one day, a necklace another, under a pink cardigan the next...
Michael Kors has been quoted as saying about women’s wardrobes: "70 percent of the clothes you own should be meat and potatoes. 30 percent should be icing and fluff—that's color, pattern, shine, and accessories. Too many women get the proportions the other way round, then can't figure out why they can't get dressed." So not only does focusing on the meat and potatoes make getting dressed easier, but it also makes it easier to repeat items often.
Lastly, I love the concept from Lessons from Madame Chic (whether it’s true or not) that if a French woman notices that her friend is wearing something she’s worn before, she’ll say “I have always loved that dress on you” instead of judgmentally noting the repetition.
If you take the last part of the advice seriously - wear more often - then the other two parts (buy better, buy less) become easier. If you know you’re going to wear something many times, you’ll be more comfortable spending more and searching for better quality.