This is the shoe that started the FiveFingers craze. While there are now 20-plus FiveFingers models, many people still prefer the Classic. The main reason is that all new versions involve more material either on the top of the foot or the bottom that removes a little of that barefoot feel. If you are just using these for around town or working out and you don't mind the look, go with the Classic. If you are doing a lot of trail running or hiking, go with the Vibram FiveFingers KSO, which is more secure and does a better job of keeping rocks and detritus out of the shoe. If you are running on pavement, check out the Vibram FiveFingers Bikila, or if you are doing serious trail and off-trail travel, consider the Vibram FiveFingers TrekSport.
Vibram FiveFingers Classic Review
Cons: Not ideal for cold conditions or sharp talus and rocky trails.
Our Analysis and Test Results
These give the most barefoot feeling of all the FiveFinger models. They are tied for thinnest rubber on the soles and have the least amount of material on the top of the foot. This makes them the most breathable model and fastest drying. It also makes them the best of all the FiveFingers at reaching the whole goal: a shoe that has all the natural feeling of being barefoot while providing protection for the bottom of your foot.
These were our favorite FiveFingers to wear around the house, in the yard, etc.
They are much faster to get on and off than other FiveFingers models. We found it much easier to wiggle our toes into their sleeves.
While there is not really any tread on this shoe, they are surprisingly slip resistant on steep dirt. This is because unlike normal shoes, you can dig your toes down (imagine a bird grasping a branch).
This model does let in more dirt and sand than the KSO, Bikila and other models with material on top. The upside is they are a little faster to clear of debris than the other models. These are less warm than FiveFingers models with material on top. When hiking in cold temps our feet eventually warmed up with the KSO and Bikila but not as much with the Classic.
These are also not as secure. If you are using these for water sports, you may find yourself missing one after a dunk.
While none of the FiveFingers will win any beauty contests, most guys find these models the least attractive. The open top of the foot looks more effeminate than the KSO or other models with rubber on top. The only people who like this look are people who like getting stares or being quized by strangers "What is on your foot?" In a year or two maybe these will be popular enough that people will stop thinking its dorky. I used to think the Toyota Prius was the ugliest car out there until everyone around me (plus myself) started driving one. Now it just seems like a normal car.
These are not warm and you can only make them warmer by wearing special Injinji socks. They are not ideal in cold or moderately cold temps. These take a little while to put on. It's not a big gripe, but you can't just slip them on. You have to work your small toes into their individual sleeves.
This model also comes in leather uppers for a more urban and less athletic look. The KSO is a version with a Velcro strap and coverage over the top of the foot.
— Chris McNamara