Part of leaving your comfort zone will involve spending a bit more on clothes than you're used to. Personally, I have in the past bought shirts for $10 or less, pants for no more than $30-35, and always on sale. So I had a good male friend (who knows much more about fashion than me) take me shopping last week, I loved some of the clothes I saw, they looked great. They just had price tags in the $50-100+ range, and I wasn't prepared to spend that much money, even if I could afford it, so I bought nothing... travelled 2 hours to a big city to shop and bought nothing.
But I need to leave the comfort zone of what I'm used to wearing, at least because the clothes I have right now are so old they're losing teeth and getting a tattered/torn at the edges. That may mean forking over more than I'm used to for a pair of pants. Maybe the good clothes last longer too - that would kind of make up for it.
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