We wear 20% of our clothes 80% of the time (Pareto Principle).
Traveling is a good time to see what clothes we really wear. Ever go to pack for a longer trip and you feel like you don't have enough outfits to pack that you love? Even though your closet is overflowing? That's because you only wear about 20% of those clothes in your closet. You're probably wearing the same few items more times than you think. The rest just sit there like bruised fruit. You're never going to actually pick the bruised fruit when there are your shiny favorites lying around.
Ween out those clothes you don't wear or aren't comfortable in. THEN you can see the gaps in your wardrobe and fill them in. One time while decluttering I discovered that even though I had 8 pairs of shorts, I actually had ZERO, yes ZERO pairs that fit me well enough to wear. Yet every time I went shopping I thought, oh I have plenty of shorts. Your closet can be deceiving!