It's hard to compare these to other boat shoes since this is my first pair. Sizing wise, I typically wear 10.5 for most shoes but I decided for a size 10. It actually worked out for me since I only planned to wear these with/without thin loafer socks. First wear, the leather was pretty stiff and a little tight in the toe area. It took a couple wears for the leather to finally break-in and mold around my feet. The leather also stretched enough where the small tightness in the toe is gone. Otherwise, they are comfortable as heck and look good with everything. I do plan to pick up another pair in a different color.

Take a pair of Sperrys and upgrade them to high-quality leather and double the arch and heel support and you've got yourself a Sebago Dockside. These are my favorite boat shoes. I prefer them to Sperry. I can walk around all day in these without pain or feeling like I'm wearing a "boat shoe." Only downsides: 1. They take a crazy long time to break in. The leather is not forgiving so wear socks with them for the first month or bathe them in hot salt water overnight and beat them with a baseball bat, otherwise get out those band-aids for your ankle. 2. They never really wear out. (Why is that bad?) Well, Sebagos have incredible durability. I've had a few pairs for quite a few years and they literally look the same as when I bought them. This is awesome unless you're one of those who needs the saltwater stained grungy look to make your boat shoes feel authentic. These hold up so well it's going to take awhile to make a Sebago look "worn." If you're looking for shoes that look broken in, go Sperry.

My favorite boat shoes were a discontinued Sebago model so when I needed to replace them I stuck with the brand. These shoes are classically styled, which is nice. What wasn't so nice was the break in period: I have never had a pair of shoes that took longer to break in. That includes Frye boots, old school leather hiking boots, etc. I was in pain, daily, for about a month and a half. If I hadn't worn them outside I would've returned them rather than endure that break in period. Even after that was done they were never what I'd call comfortable (compared to other boat shoes I've owned). Other minuses include the leaky soles (no waterproof-ness here) and about a year in the stitching near the lower eyelet as torn out. Wanted to love them but ended up just living with them.

My experience with Zappos was great! My son loved the shoes, and I love doing business with Zappos!

I just purchased a pair of Docksides for the first time (my first pair of boat shoes ever) and they are incredible. I'm extremely satisfied with my purchase; the fit is very nice and true to size, they look and feel great and are definitely worth the money. Zappos shipping was fast and FREE, gotta love that! I would certainly purchase products from this site again, I'm very satisfied.