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IMO this isn't really a problem that can be solved via Personal-Stylist-as-a-Service or a Trunk Club type offering.

Engineers dress like shit because they don't prioritize personal appearance very highly. The only thing that will fix this is to get an engineer to prioritize personal appearance more.

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So all the site needs to do is help the engineers understand the benefits of not dressing shittily. It's like doing unit testing or adopting a new framework. Once they dig themselves into the learning curve and begin to see real-world changes they'll become lifelong converts.

(edit) .....Or not, in which case all they lose is the same amount of time they'd invest in unit testing or a new framework. But definitely the site needs to do something to convince the engineers.

Or not.

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