What I’m Wearing: Sperry Top-Sider Cloud Saddle Shoes


Per my new career, I have started getting into men’s fashion.  I am by no means an expert, but I’m learning.  I figure, when I’m wearing something I particularly like or dislike, I plan to share that on here.  I’m more than open to input on this stuff as, like I said, I’m learning.

To start, I’d like to say that, although I own a normal Sperry Top-Siders, I don’t particularly like them.  I think they are somewhat ugly and uncomfortable.  However, they are convenient and they are a great shoe to wear for an occasion that tennis shoes won’t work in but you still want to be somewhat casual.  That being said, I think these Cloud Saddle Shoes, fit the bill much better than normal Sperry’s.  They are more comfortable, can be worn at work or casually, and, in my opinion, are much better looking.  Of course, looks are completely subjective and I am partial to oxfords and saddle shoes.

So, the Sperry Top-Sider Cloud Saddle Shoes.  These are some of my favorite shoes right now.  I should note that I have very sweaty feet (gross, I know).  I generally have to take my shoes while I am at my desk or my socks are soaked and my feet burn by the end of the day.  Besides flip-flops, these are the only shoes I own that I can wear all day without issues.  That includes all my tennis/running shoes.

The reason for this is that the shoes are canvas, which is extremely breathable and light.  These are also some of the lightest shoes I own.


Positives:  Lightweight, breathable, good looking, relatively inexpensive, versatility.

Versatility: These shoes can be worn with jeans, shorts, or if you want to dress down slacks and a button up.  I probably wouldn’t wear them on a day where I need a tie or a formal business meeting.  But they can be worn with any other time.

Negatives: No arch support, foam sole is somewhat flimsy and it seems like it wont last very long, the sole is also white so it gets dirty pretty quickly.

I’m also not crazy about the laces.  I don’t like bulky laces, especially with slacks, I plan to get different laces.



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