Why are some of the ugliest sites on the Web also the most popular?

If you’ve been on the Web in the past decade, you’ll likely have visitedReddit, Craigslist, Wikipedia, 4Chan, Hacker News, or The Drudge Report at some point. While these sites are all vastly different, they have two things in common: they’re all extremely popular among their audiences and they all look, well, terrible.

Web technologies have come so far in the past few years and designers now have a vast array of tools and techniques at their disposal. Yet these sites feature unflattering layouts that have no connection to the modern design philosophies seen around the Web today.

Why do some of these sites look like they were built in the 90s? Where are the clean layouts, carefully selected fonts and complementary colors?

For the record, The Drudge Report and Craigslist are indeed more than 20 years old — both were launched in 1995. Wikipedia just turned 15 last month. Reddit has now been around for 10 years, while image board 4chanis going on 13.

The thing is, it’s not always easy to say at a glance whether a site is well designed or not. You might be able to quickly decide whether it looks nice, but there’s more to good design than merely creating an aesthetically pleasing layout. You also have to consider how usable a site is and if it helps visitors find what they’re looking for or accomplish the task they have at hand....more