Band of Outsiders Short Sleeve Madras Shirt, $180

A good madras shirt is a beautiful thing. Too often guys get scared about doing plaid in the summer because they think they look “overly preppy” and ridiculous. But it’s the prep that understands that plaid isn’t just for the fall, and because of this, he can own the madras look. But once upon a time, madras was a common fabric as the prepster had established his place at the core of American style. We think it’s time you gave the madras shirt a chance–you’ll be surprised at how good you can look.

The thing about madras, like all plaids, is that is comes in loads of colors and styles. While you can find madras shirts in bright colors and in those elaborate patchwork designs, we want you to keep it a little more tame–especially if you’re just getting your first madras shirt. That’s why we love Band of Outsiders short sleeve madras shirt. It’s got a great color palette and a pretty simple pattern, all things considered. It has that trim fit like all of Band’s shirts, and the short sleeves will work perfectly in the summer.

Get Band of Outsiders Short Sleeve Madras Shirt at South Willard for $180.

Andy Hunt, co-founder of Warby Parker

Warby Parker might just be one of the coolest brands in the fashion business. They make super high-quality glasses, sell them exclusively online for only $95 (with or without a prescription), and let you ship up to five pairs at a time to try on for ten days at home. From thick frames to classic and conservative frames, the brand’s lineup has it all, and we were thrilled to speak with Warby Parker co-founder, Andy Hunt. (And here’s to Prepidemic’s 1,000th post.)

Prepidemic Magazine: How did you get the idea for the brand?

Warby Parker: I actually graduated from Brown in 2004 and I worked in New York for a number of years. I lost my glasses all the time, so I would always have to go to Lens Crafters, or the boutiques. And I would be spending a fortune and couldn’t believe it would be that expensive. So I figured there had to be a solution.

Additionally we found Restoring Vision, which is one of the largest nonprofit eyewear distribution companies. And what they do is basically distribute eyewear to people who are earning less than $4 a day.

So basically we thought we could design and produce eyewear what was as high if not higher quality than a lot of these glasses by Chanel and Prada. So we did a whole bunch of market research, developed some designs and that’s how it got started.

Prepidemic Magazine: How are you able to provide these high quality frames at such a competitive price?

Warby Parker: The key is really cutting out the middleman. The industry is basically an oligopoly with these large companies, and what they own is manufacturing. The glasses aren’t actually made by Chanel. They’re not designed by Chaenl. What they do is sell these factories’ product and stamp their name on the exterior of the frame. So these places design them, they manufacture them, and they sell them through Lens Crafters and Pearl Vision. So they own the entire production process from start to finish, and they can basically sell these glasses for whatever they want, so it’s a giant rip off.

So we cut out the middleman and do all of our sales from the internet, which certainly reduces a lot of the cost for us. But mostly we choose not to charge an astronomical price.

The Fillmore in Tennessee Whiskey

Prepidemic Magazine: What’s your role in designing the frames? Are you guys just taking other factories’ designs?

Warby Parker: We design 100 percent of the frames in house. We design, we manufacture – all in house.

Prepidemic Magazine: How’s stuff going since the big write-up in GQ?

Warby Parker: Obviously being in GQ has been really good for us. We’ve got a great publicist, she’s very good for us. Obviously it generated a lot of sales and we’re growing as rapidly as we possibly can. It’s a pretty exciting time.

Prepidemic Magazine: How’d you get the idea for home try on? We actually don’t wear glasses but often feel a bit awkward walking into a store and trying glasses on that we want to wear, only to tell the salespeople that we don’t have prescriptions. Was part of the idea to make things less awkward?

Warby Parker: That’s actually an interesting angle – I have heard it in the past, but I wouldn’t say it’s the primary reason. The home try on is really for the fact that we really feel like we have a great product. All of our plastics are custom fitting and the designs are great, and we believe that if you get the product in front of someone, they’re going to be compelled to buy it.

Prepidemic Magazine: So what’s on the horizon for you guys? Any new frames coming out?

Warby Parker: Sure, we are constantly designing and tinkering. We’re going to add some plastics, but right now we’re really focused on the more boring but very important stuff like prescriptions.

Prepidemic Magazine: Do you guys get customers buy frames without prescription lenses and wear them with the clear lens?

Warby Parker: Yes. A large number. I think very fashionable, urban-type settings there are a lot of people wearing what we call a “plaino lens” which is just a high quality plain lens with no prescription. A lot of the editors and very fashion-forward people are wearing plain-o lenses.

Prepidemic Magazine: How do you feel about people wearing plaino lenses… you wear prescription lenses, right?

Warby Parker: So I actually wore prescription lenses my whole life, but I had Lasik surgery right before I went back to school, before we started the company. And now I wear plaino lenses. I wear frames without prescription lenses all the time.

The Miles in Sandalwood Matte

Prepidemic Magazine: That’s awesome. We’re trying to push more guys to go for that look because we think glasses are such an awesome accessory and compliment to your wardrobe.

Warby Parker: Oh absolutely, and we’ve always felt that way. I think that part of our business is doing prescriptions and getting the absolute right prescription, but we see our glasses looking great on people that don’t need them but just want to wear them as a fashion accessory.

Prepidemic Magazine: How are the monocles selling?

Warby Parker: (Laughing). It’s doing well, you know, I’d say we have certain people who get them with a prescription in them, and a bunch of people want it as a plaino lens, as an accessory to just show people. We’ve sold out of a bunch more popular frames we’ve had, but it’s doing well. It’s an attention getter, both for us and the people that wear them. And actually a lot of older people, they’re into buying the monocle. They read menus at restaurants and need to see it up close.

Prepidemic Magazine: What should a guy be looking for when he’s trying on a pair of glasses?

Warby Parker: The one thing you see over and over again, are that glasses are really very personal. So that’s one of the reason we offer the home try on – we want people to take time with them, and that’s also why we offer the virtual try on – you can go on our website and look at a pair of frames on an uploaded picture of your face.

And everyone’s so different, so that’s why we try to have a complete line of glasses: 27 shapes, 3 or 4 colors per shape.

So we offer some of the bigger, thicker, chunkier frames – which I’m a huge fan of and are what I wear when I’m out – the Huxley’s, the Filmore’s, the Roosevelt. And then we have more traditional, smaller, boxier frames that can be a bit more functional and professional for the office. It’s all to offer an array of options for personality and what people tend to use them for.

We’ve always said glasses are an accessory. So you might have a big thick pair of chunky frames for going out. And you might have a smaller more conservative pair of frames for the office or for going to class. And then the colors – we have a baby blue and then there are much more traditional colors.

Prepidemic Magazine: Any plans to launch some wire frames?

Warby Parker: We’d like to. I think we have a set of designs we’ve looked at and thought about for wire frames. They can be a bit more complicated to produce. But right now we want to make sure we’re perfect in the areas we’re dealing with now. But we’ve definitely thought about it.

J. Crew Ludlow Blazer, $298

Ralph Lauren Silk-Linen Tweed Vest, $265

Rugby Oxford Shirt, $60

Brooks Brothers Black Fleece Striped Tie, $150

J. Press Tie Bar, $48

Epaulet Tapered Flannel Trousers, $185

Asos by Trickers Tassel Loafer, $131

This is a look that we’ve really been loving of late, so we figured we would put it together for all of you out there. It seems like every season people think it’s time to jump on the three-piece suit bandwagon–not that we don’t love three-piece suits–and we’ve found it a little bit tiresome to hear about the trend season after season. What people could stand to hear about is using three-pieces, but mixing and matching how you do it.

So for this post, we’ve utilized a simple blue sport coat, a pair of trim flannel trousers, and a tweed vest to make our three-piece arrangement. Now, one could also just throw a tweed vest into a navy suit, but we wanted to have a little more fun. The vest is one of the most overlooked pieces in a man’s wardrobe, but it’s can really show you know what you’re doing if you pull it off. And we’re not talking the JT vest-over-the-dress-shirt-look, we’re talking about mixing a vest in with your jacket and trousers.

This is a great look to get a little preppy on, so get yourself a worn-in striped oxford shirt and pair it with a solid striped repp tie. Now the trick to add that extra bit of flair is to use your tie bar to give the tie a little air under it. It’s that extra bit of effort that will really put everything together. Finally, chose a smart brown shoe that will fit in with the classic look. We’ve chosen a simple tassel loafer, but you could go for a wingtip or a cap-toe just the same.

J. Crew Ludlow Blazer, $300 at J. Crew

Ralph Lauren Silk-Linen Tweed Veest, $265 at Ralph Lauren

Rugby by Ralph Lauren Oxford Shirt, $60 at Rugby

Black Fleece by Brooks Brothers Striped Tie, $150 at Brooks Brothers

J. Press Oar Tie Bar, $48 at J. Press

Epaulet Tapered Charcoal Flannel Trousers, $185 at Epaulet

Asos by Trickers Tassel Loafers, $131 at Asos

Rugby University Chinos, $70

This list of Preppy Essentials wouldn’t be complete unless we made a point to promote the most powerful weapon in the prepster’s arsenal: Color. A well-dressed prepster isn’t afraid to play around with color and shade. And there isn’t a place where he finds an outlet for his color obsession more than his chinos. Pink, purple, orange, green, and white are all colors found on the bottom halves of men all over The Hamptons and Nantucket, and using our deductive reasoning, we’ve been able to conclude that these are the preferred styles of the preppy male.

In all colors of the pastel rainbow

But there is more to the stylish prep than just coloring, for it is not hue alone that makes the chinos bold. The stylish prep knows that the fit is just as much of a statement as the tint and this is why his chinos are slim and hit right at, or before, the ankle. The fit mixed with the color is what makes the look, and that’s why the prep would turn to Rugby for chinos that fulfill his criteria. They’re slim, but not tight, and have just the right colors to give him that little bit of extra umph that he needs when he is summering.

Get your pair of Rugby University Chinos for $70 at Rugby by Ralph Lauren.

And of course, there was his attitude. Taking a drag off his skinny cigarette, leaning back in a chair with his feet up on the table and his wraparound black shades shielding the sun, Marcello’s nonchalance epitomized sprezzatura, or natural elegance.

Whether you like the design or not, you have to accept them as the staple piece for prepsters in the winter. They’re one of the best options for an affordable bad-weather boot as they start at just $80 and will last for plenty of seasons to come. If you don’t have a pair, then you probably pick one up because there’s going to be a point in your life when you wear them–so why not make that time now?

You can get the L.L. Bean Boot in all shapes and sizes at L.L. Bean.

For more on the bean boot check out Sartorially Inclined’s Bean Boot Project.

Persol 714 Sunglasses, $210

Woolrich Woolen Mills Carlsbad Jacket, $527

Gitman Brothers Vintage Patchwork Shirt, $174

L.L. Bean Signature Corduroy Shorts, $49

Vans Authentic, $42

My appreciation for surf and skate culture, both new and old, runs deep so when the weather warms up I tend to look towards the left coast for inspiration.

The effortless cool of guys who spend their days shredding is undeniable. With complete ease and without a care in the world, surfers and skaters alike are often the best dressed kids on the block. When clothes aren’t really your first priority it’s easy to look natural and smooth – qualities that are easy to come by when you really could care less about what’s on your back. While I obviously put some thought into my gold coast inspired look, my attempt was to channel nonchalance and the swagger that often comes with dressing comfortably for whatever lifestyle passions one may have.

The look is anchored by the hands down greatest sneaker off all time, the Vans Authentic. I won’t even get into the heritage of Vans because, well, I would end up writing an entire dissertation. No matter what your personal style you should have a beat to shit pair in your closet. End of Story. For up top I decided to go with a white tee and the new Gitman Vintage surf patchwork madras shirt. The white tee, much like the Vans Authentic is a staple and needs no further explanation. The Gitman shirt is loud, but then again so is a surf rat. It ties in perfectly with the theme and has the best fit in the business.

All of this is topped off with Woolrich Woolen Mills Carlsbad Jacket from the S/S 2010 collection, which is all surf inspired. Designer Daiki Suzuki looked to the same guys for inspiration as I am right now so it was only fitting to include the best jacket of the season. The new L.L. Bean Signature cord front pocket shorts may seem a little out of character since L.L. Bean is as east coast as you can get, but the old school cut and fabric of the short work great with the whole vintage vibe of the kit. Finally we have tortoise shell 0714’s because you only need one great pair of shades and who are you going to look too besides the Italian icons for that last bit of sartorial flair?

Persol 714, $210 at Sunglasses Paradise

Woolrich Woolen Mills Carlesbad Jacket, $527 at Oi Palloi

Gitman Brothers Vintage Patchwork Shirt, $174 at Context

Calvin Klein White T-Shirt, 3-pack for $29 at FreshPair

L.L. Bean Signature Corduroy Shorts, $49 at L.L. Bean Signature

Vans Authentic Shoes, $42 at Zappos

Lands’ End is an all star in the affordable clothing business, but their Canvas line aims to update their clothing in a contemporary way, with an emphasis on functionality and wearability — all the while retaining the worn-in, classic feel of American goods.

And, boy, did they nail it with the Heritage Oxford Shirt. The kind folks over at the company sent us over one of the shirts for a test drive, and all we can say are good things. It comes in six colors – striped and non-striped, and the fabric is not too chunky for the hotter months, and soft and smooth on the skin — more-so than any oxford we’ve worn before. Expect quality construction, with a visible gusset on the side-seams. Thick buttons add a nice sense of quality.

The detailing is fresh and up-to-date: there’s contrasting fabric (just plain oxford cloth) at the vent and inside the cuff — so turn those badboys up and show the world what’s inside there. We really dig the collar; it’s a little smaller than most, so it’s a tad more contemporary and sporty.

But what really sets this shirt apart is the fit: you normally have to work to pay off the bills for an oxford shirt that fits so well, but at $34.50, you can have this piece. It is slightly slimmer than a typical J. Crew shirt, and they shortened the tails a couple inches. So wear it untucked and look effortless (and not awkward, which happens when many shirts go untucked), or throw on a slim tie and a jacket… it’s really the perfect sport shirt.

Get the shirt — or many of them — here.