Out with the Old, In with the Same!

There comes a time when you just need to move on. Friends keep telling you its’ time to let go. You know you should, but you just can’t bear to separate yourself from something that you once found so much joy in. What’s a person to do?

Buy an exact replica of course!

After reading the article in the NYT regarding the idea that “If women shop, Men Stockpile“, I started to wonder if I fall into this typical male buying trend. The answer: a little bit, yea. I have always been a very frugal shopper, but not like the typical frugal person. While it should not be shocking that I will go out and spend $75 dollars on a single pair of jeans (this is NYC after all), what most people don’t realize is that I’ll visit at least a dozen different stores over the course of a few weeks to find that perfect pair. Styles, fabrics, and sizes seem to change at a very quick pace within brands, especially for jeans, so a pair I bought 6 months ago that I have since grown to love (and depend on) may no longer be available. Do I wish that I could buy multiple pairs of the Levi’s skinny jeans* so that I had some in reserve as I wear them out? Of course, but at $75, I’m barely getting the first pair, so I’ll take what I can get and worry about the next pair later.

This restriction has led me to playing the dangerous game of fashion roulette. Will that same pair of shoes be around in 5 years when you’ve worn the other ones down so far you mine as well be Fred Flintsone? If you dislike something you purchase, that’s easy. Just don’t buy it again. However, if you find something you love, all you can really do is keep your fingers crossed that it will still be available when you need to replace it (or get good at ebay/amazon/google searching).

Now, I should be completely up front. Underneath the bow ties, cardigans, and childish good looks (so my mom tells me), I have the heart of a 65 year old man. The best way I can describe myself is that I am a 65 year old man, trapped in the body of a 27 year old, with the energy and enthusiasm of an 18 year old. I can throw down with the best of them absolutely, but also enjoy the slow pace of life at time (as slow as you can get in this city at least). I know what I like, and while I’m not afraid to try something new and take chances, I also find my sanity and happiness in the things I find comfort in. The “comfort” items come in many different forms (most of them I’ll share over the course of time), but there are a few that pop right into my mind: My dog (first), a “grandpa sweater” (old man), a pair of slippers (old man pt. 2), and the star of this post, a good pair of boat shoes.

Now I have to say, a good pair of boat shoes can become the star of your wardrobe. For some reason, they float in the grey area between casual and semi dressy and therefore can be worn in almost any occasion. Would I wear them to my wedding? Well, actually, I might! Not sure they would go with my Tom Ford suit that I plan on wearing though.

So a few years ago, I was living my life without the knowledge of boat shoes. On a day trip out to do some shopping (not barshopping, just regular shopping) I came across a pair of Blue and Green Sebago Leather Boat shoes. Even though they were my two signature colors wrapped into one shoe, they were also $70, and for what I thought would be an infrequently used shoe, was higher then what I was willing to pay……at first. Luckily, at the insistence of my shopping compadre, I decided what the hell (Hey, I got paid the day before) and walked out with my first pair of boat shoes.

Photo from DaVinci Shoes NYC

To say that breaking the shoes in was difficult, is a drastic understatement. They absolutely tore

up my feet (note to self, wear socks at first) to a point where I thought I had had enough. Boat shoes were proving not to be for my apparently tender feet, but I endured the pain and stepped on, and sooner then I actually noticed, the pain subsided, my feet toughened up, and the leather formed to fit the contour of my foot. After that, I was hooked.

Now while I have been in the city, I have worked in jobs ranging from a Broadway Theatre Bartender to a Stock Exchange Analyst with required dress codes ranging from street wear to business casual and everything in between. Hands down, these boat shoes have been along for that ride, and show off their war wounds with pride. Honestly, it was becoming embarrassing to wear shoes that had come apart at the seams, separated from the sole, or had lopsidedly broken laces, but I just couldn’t stop wearing them. As my “go to” shoe, I couldn’t just retire them. So I set out to find a new pair. Not just a new pair of boat shoes, but an identical pair to the ones I already had. After all, the color combo already went with 95% of my wardrobe so I didn’t have a choice even if I wanted to!

So I started my search, and pretty quickly (thanks NYC) found an identical pair for $70. Like I said, I’ve got no problem spending a little money if I know I’m getting the quality and longevity that my clothing budget requires. Was breaking them in easier this time? Ha, not in the least, but at least I wore socks this time!**

What’s my point you ask? Well, try something new, but don’t be afraid to stick with what you know! Needless to say, I think the new pair was much overdue! Told you I wore those suckers down!

Before and After

Stacked up Quality


Viva la Boat Shoe,


*By “skinny” jeans, I mean semi skinny, not flesh form skinny.

**Any color except white will do. White socks and boat Shoes still remind me of socks and sandals, which is a definite no no.


One thought on “Out with the Old, In with the Same!

  1. Pingback: There’s No Mocking the Moccasin « Style of Mind

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