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I get a lot of my husband's clothing (shorts) at Lands End online. They are fairly expensive but if you watch for sales you can get good deals. He likes these shorts because he knows how they fit. Jeans I get online based on the ones he has. Nice slacks, again usually Lands End because I can have them hemmed to the length he needs. I don't know where you live but here in the South they have Belk's and they have clothes for older men and women. I have also gotten him some things at Kohl's.
I looked at a few pages of hits on Wrangler Cowboy Cut Jeans. The highest price shown was $35. I wonder if the mailed flyer from a ranch supply store had typos for the jeans prices. Like someone printed a 7 every place that should have been a 2. ALL their prices for Wranglers, not just the Cowboy Cut, were oddly high. And yes, there are real working cowboys here, so I had difficulty believing they could afford $75 per pair.
Guy over 60 here, seems like all clothes are geared towards men in their 20s & 30s. Are there stores that cater more towards us older guys?
I have had the same issue and after a lot of looking/shopping found stores like SteinMart (a great find!), outlet center stores like Columbia, Van Heusen or GH Bass & Co stocking plenty of regular fit sizes and pretty much all JCPenney stores (lots of regular fit options, wide range of sizes IN STOCK-IN STORE) the best in terms of selection and in store inventory. Online retailers like LL Bean and Land's End are good choices too.
OP, I don't think you are quite at this stage yet, but when my elderly dad started having trouble doing up his shirt buttons and zipping up his fly, I was relieved to find Buck & Buck:
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