Authentic Original Boat Shoe – Sperry $100

I think the boat shoe trend may be a spring flash in the pan but I have been a long term devotee.

Can you really call yourself Gen X if you did not wear your jeans pegged with Eastland boat shoes with the laces coiled?

But I digress.

This spring you can indulge your Gen X years in varying degrees of luxury. I have to chuckle at the $400+ price tag on some of these versions of the boat shoe so I do have some thoughts…

Jia Boating Loafer – Veronica Beard $330 – Kind of looks like the designer started with the boat shoe in mind then got seasick and ended up with a driving loafer.

Eastland Falmouth Loafer – DSW $64.98 – This is the 90’s mainstream version of the boat shoe, a bit on the clunky side but nostalgic.

Stuart Weitzman Tinsley Suede Boat Loafers – Neiman Marcus $495 – I feel emboldened by the price to talk a little smack about these boat shoes — they are definitely trying too hard, like the Wall Street bro of boat shoes.

The Boat Shoe – Rothy’s $119 – Not a bad look and not a bad price for folks looking for a quality, comfortable version – and practical for a boat shoe, these shoes can get wet!

Sebago Brown Tan Portland Crazy Docksides – Tuckernuck $195 – Almost as classic as the OG Sperry boat shoe but definitely not as economical.