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We’ve really got a soft spot for a gorgeous shoe with a twist. As much as we love a great pair of loafers or wingtips, sometimes you just want to wear something a little different than anyone else. Sometimes you’ll stand out with your jacket, shirt, or trousers, but never underestimate footwear’s ability to help you look stylish without going overboard. If you share this desire with us, then we would like to point you in the direction of Mr. Hare. These Italian-made shoes have that tongue-in-check attitude, but won’t you leave you looking like a jokester. We’re loving their Spring/Summer 2010 collection, as it is a real breath of fresh air from what we usually see guys wearing in the warmer months. In an interview he did with Selectism, Mr. Hare said, “My SS10 collection is named ‘Hot Steppers’ and all the styles are named after dancehall generals who have burnt down dancehalls all around the equator. Cachao, King Tubby, Phil Spector, J.Dilla, Jerry Lee Lewis etc. So yeah – don’t test the champion sound.”

Jack Wills Knitted Hoodie

Ralph Lauren Essential Lounge Pant

Tod's Lacetto Gommini

With men’s fashion de-formalized as it is today, dressing for comfort should never mean looking sloppy, and can even be a good chance for some creativity. This hoodie by Jack Willis is trim across the body and sleeves, and the wool is a step above that boring gray sweatshirt. The lounge pant has some of the softest cotton you’ll ever feel, and the great cut and draping still gives you that sleek silhouette. Finally, how about a steel blue pair of driving mocs to add some color into your life (especially appropriate if you’re in sweats and feeling a little blue)?

Jack Wills Knitted Hoodie, $140 at Jack Wills

Ralph Lauren Essential Lounge Pant, $195 at Ralph Lauren

Tod’s Lacetto Gommini, $425 at Neiman Marcus

We were having a talk about whether having a uniform was stylish and the one person we kept coming back to was Thom Browne. He’s known for always wearing his grey suit with a white shirt and tie, and has been a major catalyst in bringing this aesthetic back in a big way. Although we might not find his particular style to be the most appealing, we really respect his philosophy behind it.

There is definitely something to be said for the man who has an attachment to an aesthetic. We really liked Colin Firth’s character George’s approach to uniform in Tom Ford’s film A Single Man. For him, he sees his uniform as a part of himself. He is not complete until he is wearing the clothes he is most comfortable with. We’ve attached some photos from Thom Browne’s ad campaigns showing his particular affinity for uniformity. We’d love to hear your thoughts on whether or not a uniform is stylish.

The Brown Wingtip

This is the first shoe you should buy. The brown dress shoe is the shoe you will wear with your grey and navy trousers, and thus a shoe you will wear very often. This is also the shoe that you should not skimp on. Invest in a quality wingtip and you will not regret it. It will be the centerpiece of your footwear collection for years to come. You want something slim, but not too slim, and with gorgeous, preferably antiqued, leather. There are a few options you should check out when looking into a quality wingtip, and they will all cost you. Of course, you could go with Church’s–their reputation for quality footwear speaks for itself. There is also Barker Black, which we promote all the time–their Archdale wingtip is one of our absolute favorite shoes. But we want to point you in a different direction this time.

Crockett and Jones’ handmade shoes are some of the finest footwear around–and have been since 1879. The Northampton-based shoemakers pride themselves on their gorgeous antiqued leathers and first-rate Goodyear construction. We can find no better example of their expertise than their Clifford Wingtip. It is such a strong and sturdy shoe, yet is still slim and flattering. The ornamentation is original, but not overly lavish. And finally there’s the leather, which is the real highlight. These are the kind of shoes that are going to age so well, you’re going to like them more in 5 years than when you bought them.

Unfortunately, we can’t all spend $700 on shoes. Luckily, there is a brilliant pair of wingtips made by Loake that will cost you less than half of those made by Crockett and Jones. If $256 seems high for you, we suggest you rethink. If you were to buy a pair of $100 wingtips, you may have them for a year or two, but they will quickly die. These ones by Loake will last you a while, and look good for their entire lifespan–so think of it as an investment.

The Simple Black Dress Shoe

How often you choose to wear this one is entirely up to you. Of course it is a necessity for most formal events, but it is also something that can look very good when done properly. This will also look good with your trousers, but doesn’t give quite the warm vibe that a brown wingtip will. However, you can’t wear your wingtips every day, and you need some variety in your footwear so that you don’t become boring. Now, there are a few styles you can choose from when choosing a black dress shoe. Of course, you can go plain toe, but we only suggest doing so if you’re ready to pay some significant bills because you get what you pay for in the plain toe shoe game. Our suggestion for an affordable black dress shoe comes from Barney’s… like actually made by Barney’s. Their in-house line always turns out some really awesome stuff, and these cap-toe dress shoes are no different. For $160, you can snag some surprisingly solid Italian-made shoes that won’t let you down.

Once again, we want to reiterate that in the world of clothing and shoes, most of the time you get what you pay for. So if you’re really trying to look like a million bucks, you’ll have to fork up some cash to do so. Luckily, there is an easy way to justify such expenditures. Quality shoes are an investment. If you buy an $150 shoe, it might last you 2 years–which is $75 a year. But if you buy a $582 pair of Dries Van Noten lace-ups, you could be wearing these for at least ten years with a couple refurbishings, which would bring you to around $80 a year. Oh, and did we mention how awesome these guys looked?

The Loafer

Once you have your dress shoes figured out, you can start to move into casual footwear. And of course, the first casual shoe you must buy is a loafer. It’s the most classic of all casual shoes and will transition the best between work and play. There are a few options to choose from here, all of them good. You could get a tassel loafer, penny loafer, or horsebit loafer. We love ourselves a tassel loafer, but they’re not for everyone, so we will suggest going with one of the other two loafers. Of course in the world of loafers, there is one name that shines above all the rest: Gucci. The Gucci loafer is money in the bank. Their penny loafer is super-slim and very French, which means they’re not for every guy. However, we are hard-pressed to find a guy that doesn’t look good in Gucci’s Horsebit Loafers. There is absolutely no shoe that will look better with age than these, as shown by the picture above. We prefer them without the ribbon, but it’s a matter of personal preference.

Gucci isn’t the only big name in the world of loafers. There happens to be a much more affordable (and American) one that’s been making quality shoes since 1876. G.H. Bass & Co. is probably one of the most popular brands in the history of Ivy League style. They’ve been making their Weejun Penny Loafer since 1936, which means they’ve had more than enough experience to perfect it. And the sure perfected it when they came out with their newer, slimmer “Dover” model in March of ’09. This isn’t quite what your Dad wore back in the day, as they really made an effort to modernize it for younger and hipper guys. There are few shoes under $100 that are going to treat you as well as the new Bass Weejun.

The Desert Boot

We love our desert boots here at Prepidemic. It’s amazing how many different forms they can take on, just by changing the leather and sole. You can get a pair with simple leather and a crepe sole to inject a little bit of a rugged vibe into your look. You can keep the crepe sole and switch to a suede upper if you want something a little more preppy. Or you can get something with a suede upper and a leather sole to feel very crisp and Italian. And who better to buy your desert boots from than they guys that did them first? Yes, Clarks Desert Boots may just be the shoes that will give you the most bang for your buck on this list. It’s amazing how comfortable and durable they are–not to mention stylish. We don’t really need to elaborate on them because you should already have a pair, and if you don’t, order yourself one. Go with either the classic beeswax leather or the dark brown suede.

Now if you really want to go above and beyond, there are some options that will look a little better than your Clarks. It’s really important for us to stress that there really is very little reason to buy your desert boots from someone other than Clarks. The biggest reason would be that you want a slightly dressier boot, in which case, we hear you and are more than happy to oblige. If you’re looking for a dressier desert boot, the English are the ones that got you covered. In particular, we’re really digging Grenson’s model as it has a nice slim leather sole and a gorgeous dark bown suede upper. For $300, you’ll be paying the same price as you would for about 4 pairs of Clarks, but hey, they do look pretty fine.

The White Sneaker

Adidas Stan Smith

The last shoe you need is the one that is easily the most casual, but that doesn’t mean you can’t look good in them. The white sneaker has been the go-to shoe for every college kid since Americans got hooked on sportswear way back when. It’s something you most likely already have, but that doesn’t mean you shouldn’t invest in better looking and ultimately more timeless pairs. It’s a pretty clear-cut formula here: simple lines, no ornamentation, and a sleek (but not super-slim) shape. Back in 1965, Adidas made the first perfect white sneaker. Named after one of tennis’ greatest champions, Stan Smith, the shoe has been one of the most popular and recognizable sneakers on earth. For $60, there isn’t really much of a reason not to pick up a pair.

The other champion of the sneaker game is Common Projects. The minimalist footwear company has been making some of the most popular sneakers out there since they burst on the scene in 2004. Made from premium Italian leathers, these aren’t your average sneakers, but for over $350 they better be pretty extraordinary. Many of you might short-circuit thinking about tennis shoes going for that much, but many true aesthetic-obsessives will find more than enough in the Achilles Low to justify their purchase.

Wellington Black, $395

If you’ve noticed us promoting velvet slippers a lot recently, then you shouldn’t be surprised that we’re highlighting the company that does it as well or better than anyone else out there. With almost 17 years in the business, Stubbs and Wootton has really hit their stride by offering an array of velvet slippers, needlepoint slippers, and loafers that ought to satisfy anyone with enough flair to put a pair on. Their collection has everything from classic crests to skull and crossbones. That ought to give you the idea that while they understand that the velvet slipper is something classic and elegant, it is also something that most people shouldn’t wear too seriously.

Hunt Brown, $395

Their tongue-in-cheek approach is something welcome in the game of footwear, as we have seen Barker Black really capitalize off of this style as well. This has also helped them bring the slipper into the 21st century, as most people regard it as a stuffy high-society formal shoe. So have fun and let loose, pick up a pair of slippers and show a little ankle. And if none of their styles are for you, then head to their bespoke section and pick from a variety of syles, monograms, and motifs that aren’t offered in the current collection.

Skull Gold, $395

Stubbs and Wootton locations:

987 Madison Avenue, New York, NY

14 Jobs Lane, Southampton, NY

4 Via Parigi, Palm Beach, FL

$215

When you’re building up a respectable wardrobe, organization is key. It’s great to have all of the basics, but as we all know, a lot of times its the little pieces that really make the difference: watches, cufflinks, stud set, tie bars, tie pins, collar bars. You have so many little pieces that you really should consider investing in a jewelry box that will house all of your little knickknacks. Not only will this come in handy when you’re rushing before a dinner party and can’t afford to go looking for your favorite collar stays, but it is also something that will look great on your bureau. Get one monogrammed and keep it with you as long as you live.  You won’t regret it. And if your buddy busts your balls for having a jewelry box, you’ll get the last laugh when he shows up to the party with only one cuff link.

$55

$75

Ralph Lauren Anthony Wool Gabardine Black Suit

Ralph Lauren Wool Turtleneck

Barney's Cashmere Scarf

Stubbs and Wootten Velvet Slippers

By using a couple different pieces, your black suit has become the canvas for something much more spectacular. Of course you’ll want a solid base, and we think that you can never go wrong with Ralph Lauren when it comes to just about anything. Moving from there, get yourself a black turtleneck as it is a really modern kind of look. What really makes this look complete is the two key components that really will separate you from the pack. First, equip yourself with a red scarf. The red will pop off of your black outfit and will get more than a few double-takes as you walk down the street. And second, ditch your simple black shoes and have some fun. As long as your pants are nice and trim, a pair of black velvet slippers will show that you have a little more panache than the regular guy.
Anthony Wool Gabardine Suit, $1600 at Ralph Lauren
Ralph Lauren Wool Turtleneck, $52.50 at Ralph Lauren
Barney’s Large Cashmere Scarf, $300 at Barneys
Stubbs and Wooten Velvet Slippers, $395 at Stubbs and Wootten

A few years ago, Spurr was just twelve pairs of jeans. With the Pipe leg jeans – a masculine but form-fitting pair of straight leg denim – bolstering the collection, the brand quickly took off.

Fast-forward to 2009. The launch of the Fall/Winter collection threw designer Simon Spurr into the limelight with its luxury tailored goods, gorgeous leathers, and the always reliable denim stealing the show. Awesome peak-lapels. Youthful double breasted suiting. Great outerwear: including a trench, manly leather coats, a charcoal pea coat, and a flawless black down jacket with a higher armhole – rendering a puffy coat form-fitting, masculine, and finally non-Michelin Man-esque.

Spurr Spring/Summer 2010

Come fashion week, Spurr was all the rage for his Spring/Summer 2010 collection. Continuing to boast the best craftsmanship in the business, and maintaining his always ultra-masculine lines, the luxury designer was now mastering color better than ever: vibrant yellows in sweaters and jeans. A stunning salmon suit. A deep navy double breasted suit, three piece suit, trench, and denim shirt. Soulful brown suiting and outerwear. It was no wonder that the media couldn’t stop raving about Mr. Spurr’s newest line. Guys on GQ hyped it as the best show of the week and we might have to hype it as the best show of the year.

But it wasn’t just design where Simon Spurr did work. Administratively, he dominated. Tommy Fazio, host to the biggest title in menswear buying (and what was once Mr. Bastian’s title) – head men’s buyer at Bergdorf Goodman – left his post at the department store and joined the ranks at Spurr as CEO. They then decided to split the brand into two labels: Spurr for sportswear and leather and Simon Spurr for luxury tailored goods.

Spurr Spring/Summer 2009

It was one hell of an auspicious year for designer Simon Spurr. He topped the year off when he was named a CFDA/Vogue Fashion Fund Finalist and gained membership to the CFDA. What might 2010 have in store?