The flat that replaced the ankle boot is not a boot at all. Chunky loafers do the same job with less commitment, and they sit under a wide jean without any of the fuss. These eight are the versions with a sole worth the name.
Chunky Loafers Are the Only Shoe That Works All Autumn

The lug sole did it
A classic penny loafer is a lovely shoe and a slightly precious one. Adding a lug sole turned it into something you can wear in rain, on gravel, and with denim that pools at the ankle. That is the entire reason the loafer came back. The loafer's whole history is borrowed authority, from Ivy League campuses to City trading floors. Putting it on a lug sole took the borrowed authority and made it slightly sarcastic, which is why it worked.
Proportion is the risk
Chunky loafers only fail when the sole overwhelms the leg, which is a hem length problem rather than a shoe problem. A cropped trouser or a jean that just touches the vamp keeps the balance. The eight below sit at a range of sole heights so there is a version for most proportions. The proportion risk is real and it is the same risk the platform boot ran in the 1970s. Volume at the foot needs either a cropped hem or a very long one.
Our honest take
Buy the loafer in a colour other than black if you already own one pair. Cashew, plum and burgundy do more for an outfit and hide scuffs just as well. This is a shoe you will wear until the sole gives out. This shoe has now outlasted three predicted deaths. At some point that stops being a trend and becomes a category.


















