Shoes matching advices.

[BPL Esq]

I've noticed that on this side of the forum, we all somewhat agree that it's not nice to tell someone a purchase is bad because we don't want to impose our beliefs onto them. So with a recent poster who wants to purchase Robert Graham type shirts, most of us say nothing. If someone wants to purchase a polyester plaid jacket, we also say nothing.

I don't know what is the solution. Many may not want to look like the people who post on CM, just as many may not want to look like the people who post on SWD. Hard to give meaningful wardrobe advice without knowing what kind of look the OP wants to achieve.

I think perhaps a polite Socratic approach is the way to go in some of these situations. "I recently bought these shoes." To get things rolling, a good first question, perhaps crafted a bit more tactfully, would be "Why?" A lot of OPs in this section don't really provide much background information about why they're considering buying or already bought a particular item, but it certainly helps if we understand what they were thinking when they did so or what they envision the item will add to their wardrobe.

Part of the problem that has to be overcome much of the time is that a great many people don't think about prospective purchases in the context of their existing wardrobe or a potential wardrobe they want to begin building (as you noted with regard to those who purchase GYW shoes like artwork and have no plan in place for wearing them with clothing they wear, to the extent they even care about wearing them at all).

 

[bicycleradical]

Those look like athletic sneakers and are probably best worn playing football, running, etc.