Yes, it’s far easier to get understanding or buy in quickly (from investors, in-laws and users) when you take the shortcut of making your digital thing look and work just like the trusted and proven non-digital thing. But over and over again, we see that the winner doesn’t look at all like the old thing. eBay doesn’t look like Sotheby’s. Amazon doesn’t look like a bookstore.
The iPhone doesn’t look like a rotary phone, or an iPod+rotary phone. And on.
There’s a lot of places where skeuomorphic design is just fine: largely when it doesn’t interfere with the usability of an object. But I loathe things like bookshelves for my iBooks, and page curls, and so forth. These get in the way, as there could be so much better information display if “trying to make it familiar” wasn’t the goal.
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