It’s how you wear it
This is a guest post by Matthew Barrison. His blog is really interesting and can be found at WorkingDefinition.com
A casual visitor to this site may find it a bit pedantic or brand obsessed. Fair enough. However, since brand = lifestyle aspiration, we must ponder things a bit more deeply. The main theme behind this aspiration is fitting in and bettering oneself, a task which I find to be truly American. And on that note, I bet that you have been thinking about what aspirational appeal the American brand holds these days. Part of me doesn’t get it, i.e. the long supply chain and its remote consequences, but another part of me understands it perfectly and sees the potential for re-calibration of the system. Thus we return to the theme of fitting in to better one’s self and progeny. The American brand has long been about just that; Ralph Lauren came from a family of immigrant Eastern Jews. For many people around the world, America still holds that promise; to many of our contemporaries, however, our recent actions have led them to volubly question our long held presupposition of preeminence. Nonetheless, we strive to re-articulate that brand by getting back to what is good, aspiration, a value of timeless fashion. Sure, we get swayed by trends a little, but at heart we are there to do good and look sexy all the while.
Costal Towns and Sailing
I just took a trip to Rockport, Massachusetts, and it reminded me of how much I love costal towns. Perhaps it is the smell of the sea, or maybe the quaint shops, but walking down the streets, and to the rock pier was a really good experience for me. It is like a mini version of nantucket, with fewer shops like Vineyard Vines and Murray’s Toggery Shop. Walking with friends on a beautiful day makes the experience even better, and it causes you to forget all your problems. While we were there, we had a chance to sail in my 8 foot long Optimist (a little sailing dinghy) although it could only fit two at a time, it was amazing sailing weather and we had a really good time. I haven’t gone sailing since last summer, and this experience reminded me of how much I enjoy it. My parents own a 42 foot sailboat that I grew up sailing on, as well as taking lessons, sailing such boats as Widgeons and my favorites, 420’s. If you consider yourself preppy in the slightest and live anywhere near a body of water, do yourself a favor and go sailing the first good weekend you get. Not only is it preppy, but its a very soothing yet fun experience. Have fun!

Preppy Sneakers
Okay so first of all I apologize for using the word preppy in just about every title, but it helps the blog rank better in google, so I get more visitors which is worth it for me. So please bear with me…
Anyways back to the topic at hand. I got a suggestion to talk about shoes and so I thought I would. Today I am going to talk about sneakers, because I am young, and besides sandals, they are what I wear most of the time. Also, I am only going to talk about ones that are under $100. I understand that most preppy clothes are quite expensive, and you are paying for quality, but since it is my blog, and I don’t have the resources to spend $200-$400 on a pair of casual shoes, I am going to talk about ones that I could afford.
When going for the preppy look, there isn’t a huge variety of sneakers, but I do like the selection. I would like to mention first that an excellent alternative to sneakers would be Sperry Authentic Original Tops
iders. Sperry does have a great deal of other shoes, most of which are very nice, all of which are extremely well made, but for the preppy look, you have to go with the classic Authentic Originals. I grew up in these things, and although they can be stiff and uncomfortable at first, once they are worn in they are a damn good shoe. Topsiders, not only have a preppy feel, but unlike sneakers they can be both casual and semi formal. Of course you couldn’t wear these with a suit, but they can certainly be worn to certain parties and summer events. Sperry Topsiders are pretty affordable at $65, but ones like the Gold Cup shoes are a little out of my budget at $160. For a very similar look check out Brooks Brothers Boat shoes here
, or find other traditional ones here at J Crew
When I said before that there wasn’t a very big variety of sneakers, I kind of lied. But the truth is that most of the variations aren’t very appealing to me, mostly because many are uncreative. Preppy sneakers have become almost an after thought, because it is assumed that they aren’t really a particularly preppy item. So while skateboard companies are producing thousands of different shoes, because that is what their customers want, preppy companies make far fewer. So I’m only going to talk about sneakers that I would certainly wear, and ones that I think look good with most clothes that a preppy person would wear.
The main two variations are leather and canvas, and I think I’ve gotten a pretty good mix of both. Canvas sneakers are not quite as sturdy or thick as leather ones, but they have a much preppier feel and look.
Lacoste Shakespeare 3: A sort of blend between the boat shoe and the sneaker. These a
re $130 on Zappos, so a little pricey, but very nice looking. The alligator on the side I feel really adds something and goes well with the navy and white laces. These are good for when you don’t want to wear boat shoes, but still want a slightly preppier look than normal sneakers.
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Next there is the Ralph Lauren Roster 3 Leather Sneakers. Although I am not a huge fan
of the white and dark green, these are a sharp looking pair of sneakers, and the pony on the tongueis a nice touch. These look more like sneakers you would run in or play a sport, rather than just every day use, but they are preppy enough to go with some outfits. At $65 they are reasonably priced as well.
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Third, there is the Lacoste Recoil 2. This shoe is similar to the Roster 3 in that it has a more sporty than everyday feel, but with the flat laces and streamlined shape, it is a little bit more functional with preppy clothes. Like all Lacoste shoes however, it is expensive and somewhat hard to find. Zappos does not carry it and it can’t be found in Lacoste’s online store so I assume its quite new. Like the other Recoil sneakers, I expect it to cost around $125, when it does become available.
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Now on to canvas sneakers. The first pair I like is the Lacoste L34 Canvas Sneaker
s. These cream colored shoes look a little thicker than most canvas sneakers, so I assume they are a little more comfortable. Since they are cream colored, they go with a lot of different outfits and can be worn with both shorts and pants. That’s what I love about canvas sneakers, they can be worn with shorts without looking goofy, when leather sneakers usually cannot. The Lacoste L34’s here cost $90.
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I particularly like these Ralph Lauren Brendall Canvas Sneakers from Ralph Lauren. The gold stripes on the side make them a little more interesting, and the navy with the white toe, is very preppy looking. Just like white or cream shoes, these navy ones can be worn with a wide variety of clothes, and aren’t too expensive at $69.
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The final pair of canvas sneakers that I like are the Ralph Lauren Blake Herringbone Canvas Sneakers. A very simple and slightly retro look, these shoes have a nice logo on the tongue and le
ather back to keep them interesting. Like the Brendall sneakers, they are preppy enough to be worn with most outfits including shorts. At $59 they are also affordable. Ralph Lauren usually lowers the price of their sneakers significantly towards the end of their lifespan, so I picked up a pair of Dungan washed Canvas Sneakers for only $39 recently.
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So there you have it. Event though its the summer now, and most people are wearing sandals, its still a good time to examine your sneakers. I have a friend who thinks he dresses preppy, but he only wears white New Balances. Sorry but that just doesn’t cut it. These shoes show that there are preppy sneakers out there, and that it is still possible to have a good looking preppy outfit with a pair of sneakers.
Next time I’ll talk about Loafers and mocasins, the other types of casual shoe, and after that Sandals. I don’t know if there’s really a need to talk about formal shoes, as there aren’t really any that are considered preppy. Preppy people dress in nice clothes , and since all formal clothes are nice clothes, formal shoes don’t really have anything to do with preppiness…



