Though their shapes and ornamentation may subtly evolve, leather loafers remain in style perennially. Whether they're brand new or straight from the vintage store, some stiff leather shoes pinch and rub, which definitely takes some pep out of your step. Once worn in, however, these leather kicks not only soften up, they take on distinct weathering patterns and patina -- the process not only makes your loafers softer and more comfy, it makes them more stylish as well.

Step 1

Wear your loafers. Although it may sound like common sense, nothing breaks your shoes in better -- and softens them -- like simply wearing them. If you know you have a big event coming up and plan to sport your new loafers, wear them around the house for a few days first. Then bump it up to short walks, errands and so on, until the leather becomes softer and more comfortable. Wear a pair or two of socks much thicker than what you would normally pair with your loafers to accelerate the break-in process.

Step 2

Crumble up newspaper into wads and stuff your shoes tightly, filling the loafers from toe to heel. Leave the loafers stuffed overnight or whenever you're not wearing them to subtly -- and safely -- loosen up the leather a bit. This trick also helps absorb harmful moisture from wet leather shoes.

Step 3

Condition your loafers to soften and preserve the leather. After cleaning the shoes with a leather cleaner, massage a light coating of the conditioner into the leather with a clean, soft and lint-free cloth, and then wipe away the excess. Repeat the process for additional softening. This process restores the leather's natural oils, making the material more supple.

Warnings

  • Never try to stretch, soften or break in your leather loafers by soaking them with water. This old trick is more destructive than helpful, as it causes mildew and damages the leather.

  • Do not store your leather loafers near heat sources or dry them with a hair dryer. Extreme temperatures and dry heat cause leather to shrink and crack -- certainly counterproductive to the softening process.

  • Follow any instructions or warnings provided by your loafers' manufacturers, or the manufacturers of any leather care products you use.

Tips

  • Try on new leather loafers in the late afternoon, at around 3 p.m. At this point in the day, your feet have swollen to their maximum size, helping ensure a fit that's more comfortable even during the rough break-in period.

  • The break-in period varies per type of leather. Calfskin, for instance, softens much quicker than full-grain or top-grain leather.

  • Keep a few pairs of worn-in insoles on hand. Equipping your new leather loafers with comfortable insoles might encourage you to wear them more and break them in more quickly.

  • If you're pressed for time, many shoe repair shops offer leather stretching and break-in services for a fee.