The Sebago company has been turning out its iconic Docksides loafer for over four decades. Worn by sailors and civilians alike, the four-hole style with the moccasin-like construction has proven to be a durable leather shoe that only gets better with age. However, like many leather shoes, even a pair of Docksides could use a little help getting that broken-in feeling, especially if they are new and you don't want to wait for them to soften naturally. This task can be accomplished with the right tools and products.
Remove the shoelaces. Completely saturate the inside of your Docksides with the stretching lotion, focusing on the stiffest areas. Put on your shoes and walk around for 15 minutes while allowing the lotion to dry.
Put on a pair of thick socks and put on your Docksides. Turn on a hairdryer to the hottest setting and aim it at the top of your foot. Wiggle around your toes as you blast the hot air for a minute or two. Turn off the hair dryer, but keep the shoes on as they cool down.
Dip a cotton swab into rubbing alcohol. Swipe the swab along the inside of your Docksides until they are damp, but not saturated. Put them on and walk around for 15 minutes.
Polishing your Docksides after each wear can also soften the leather and help to break them in.