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I'd need to know where the son has a job, but the first year associates in Wall Street firms are buying on sale at Paul Stuart. They get generous salaries and are expected to dress well, even if the prices initially shock them. It's a necessary investment. On Wall Street there's no such thing as cheap suits for the first few years if you're hoping for a future there. Unfortunate, but fact.
As oldfort points out, go to the top stores for an education. I like Barney's best. When you know exactly what you look good in and can recognize quality, you'll do well at sales. Most of these young men find a salesman at a place like Stuart and have them put together a look.
You also can't compare the quality of tailoring at a discount store to what you'd get at Barney's or Stuart and this is key.
In all honesty, if someone survives a few years on Wall Street, within 4 or 5 years they will never buy an off the rack suit again. No Wall Street taunts please, it's just the way it is.
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