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If you have really expensive, high-end items, you may be better off bringing them to a consignment shop like Michaels or Second Time Around. They will work to get top dollar for them and then you get a percentage of whatever they sell them for. Check out the STA website --- they explain everything there. Here's a link to STA and one to Michaels.
I dont know about Second time around but Michaels will not take any jeans from new customers, Not even your best $250 ones. They might take jeans from their best customers (the ones who bring them Hermes bags) but otherwise they really dont want any jeans. They are very picky there. Jeans have really low resale value since they get really discounted at Nordstrom rack , Off fith, Last call etc. Your best bet is Ebay
In my experience, only vintage clothes will get you much money, although consignment would be better than retail. Personally, for some reason, second-hand jeans give me the creeps.
Congratulations on the weight, though, and let me ask: Have you considered going to a tailor and having them taken in?
Try Beacon's Closet or Buffalo Exchange. They take fashionable and in season clothing. I believe they give you 35% cash or 55% store credit depending on how much they will sell the items for. Heads up though that they are very picky. I've brought in items that I thought were amazing and they flat out said "nope".
Keep them in a box. If you are like most people, you will regain the weight and hate yourself for tossing the clothes.
No, you will not get enough to justify cabfare.
If you want the most money -> Sell it yourself online.
If you want some money but don't want to spend the time -> cosignment store
If you just want to get rid of it and getting something is better than nothing -> second hand
If you just want to get rid of it -> donate (I forget if you get tax deductible amount as gift if you donate to recognized charity 501c)
If you think you are going to boomerag -> keep the cloths like Kefir says
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