How much I'll pay depends on the item. Obviously I'd expect to spend alot less on a tank or t-shirt ($5-$30) than I would a winter coat ($50+). I'd pay alot more for custom work/sizing because ZoE is hard to fit and if I can get stuff that fits great & looks really good on her, I'd pay extra to do so. I'd probably pay up to $100 for a nice coat or custom sweater or dress.
I can't see paying more than that unless it's for a really special occasion. I know some people involve their dogs in their wedding party...maybe for something like that I'd expect to pay a few hundred for the custom work, higher quality fabric, and hand-beading, etc.
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