The Boat Shoe: Sperry Top-Siders

Sperry Top-Sider

I have been hunting for a pair of casual shoes for quite a while now. Originally I had planned on purchasing a pair of blucher camp mocs, but do to a number of obstacles such as bad reviews, not being able to try a pair on in person, and not having the funds to spring for a pair of Quoddys or Rancourts, I gave up. In order to fulfill all of my shoe needs I ended up purchasing two pair of shoes (You can see the first pair here ) for a total of $100. The first pair that I got are able to withstand bad weather, are suitable for the office and casual wear. The second pair that I purchased needed to be able to be worn without socks (so I that do not look a bigger dork than I already am when in shorts) and to be able to make an appearance in the office if necessary. A pair of boat shoes seemed like the perfect solution.

Sperry Top-Sider

Top-Siders and ChinosI purchased a pair of Sperry Top-Siders. I chose Sperry over Sebago simply because when I found the Sperrys on sale there were no Sebagos in the mall to compare them with. There were two colors of Sperrys to choose from, tan and brown suede. I found the brown suede with leather trim more attractive and believed that it would be more versatile as well. Neither model had the white sole which was once not only a mainstay, but a functional feature as it kept the deck of a boat mark free. Since I do not own or actively boat this was not an issue for me and I actually find the brown dark sole more appealing, even if it is less authentic.

Sperry Top-Sider with chinos Top-Siders with tan socks and chinos.

Top-Siders and TargylesTop-Siders with Targyles.

Boat shoes sans socks

Pardon my paleness.

My Sperry’s are more comfortable than I had imagined. In my opinion they run true to size and have a great fit. The first time that I wore them it felt as if I were wearing slippers. Afterwards I wondered why I had never owned a pair before. They look great with chinos and and OCBD at work as well as sockless with chino shorts and a polo. I am very satisfied with my purchase. The only issue that I am having now is deciding what socks to wear with them. So far I have found that tan socks look better than blue and I am not fully sold on wearing patterned socks even though I have seen it done quite a lot. I also know that by even bringing up socks and boat shoes that I am offending a lot of my readers! However, I am not yet confident enough to go to work sans socks even though my office is less than business casual. Don’t worry I am sure that I will work my self up to it!

oxford cloth button down
Jerrod Swanton is a simple man interested in simple, classic, and traditional style.

6 Comments on "The Boat Shoe: Sperry Top-Siders"

  1. Reese says:

    Enjoy your new shoes. I’ve still got a pair of Top Siders I got as a kid in the mid-late 80’s (a kid with big feet). They will get better and better with age. They look great on you!

  2. oxford cloth button down says:

    @Reese – Thanks, I appreciate it! I hope that mine last that long.

  3. Conor says:

    Nice post and nice shoes. I switched to blucher mocs but loved my topsiders until the tops started coming off the soles.

    I like sockless best, by the way. Paleness be damned.

  4. oxford cloth button down says:

    @Conor – Thanks for the comment. Laughing hard at the “Paleness be damned” comment. Also, I still want some blucher mocs. I might get an LL Bean pair since I am on a tight budget. Great blog, by the way!

  5. David Bloom says:

    I can vouch for the comfort of the bean blucher mocs-I wear them to school (teacher in a high school) nearly every day and they look good with shorts as well-
    cool blog, I shall keep reading it!

    David Bloom, Niskayuna NY

    • Laura says:

      Nostalgia…my son Matthew, attended The Meadowbrook School of Weston (MA). I bhugot him a pair of these moc type shoes and every boy in the class proceeded to purchase a pair.Hence these shoes acquired a new name “Fifth Grade Shoes.” Soon every boy in the entire school was asking his parents for “Fifth Grade shoes. As the saying goes…you do not have to be in fifth grade to wear and enjoy “Fifth Grade” shoes. Fashion truly is cyclical…the year of my son’s fifth grade was 1993!

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