‘Structured Casual’ Look

One of my favorite looks, regardless of changing fashions and trends is what I would define as “structured casual.” In contrast to the bohemian intellectual look, this style is more sophisticated and urbane as well as likely easier to coordinate with the items you already have in your wardrobe. It’s the ideal outfit for either a museum excursion, dinner date at a trendy restaurant, or even a fashionable casual Friday at the office.


The most important elements of this look are slim jeans paired with dressier items such as narrow-toed brogues, dress shirts, and ties. The jeans you choose should be tapered at the leg and dark-colored. Right now, there seems to be a trend towards cropped jeans that end right below the ankle so as to show off the shoe. Unfortunately, this is almost impossible without the aid of a tailor as almost all jeans are sized to the same insanely long length despite a varying waist measurement. Levis Matchstick Jeans ($138)


The shirt and tie combination are the driving force and also what give the look a certain elegance and refinement. Unlike the current trends, this look eschews plaid and flannel in favor of more classic styles. A white shirt with a high collar is clearly the most versatile choice but striped and other patterned shirts are other alternatives. Tucking the shirt in is an absolute must; the days of the slovenly un-tucked shirt are over. Though the skinny tie-look with a business suit is mostly finished, they still go well with this style. Solid Knit Skinny Tie ($50)


Substituting dress shoes instead of sneakers when wearing jeans is always encouraged, regardless of what style you are trying to emulate. For the “structured casual” look in particular, a pair of narrow shoes looks best with slim jeans. I wear this pair from To Boot New York on a daily basis and constantly receive compliments on them. The fading around the toe and back of the shoe is a cool effect that differentiates it from more traditional or banal brown shoes. It is important to note that even though you are wearing jeans, white socks are not permissible with dress shoes. Rather, you can display some creativity with your choice of socks, either opting for something colorful or just basic black/brown.

To complete this style, a belt is a necessity. While wearing jeans and a T-shirt offers much more discretion as to whether or not to include a belt, forgoing one when wearing a dress shirt looks remiss. Thin belts are the look to opt for as they generally work better with slim jeans.



For colder weather, adding a waist-length trench coat helps establish the lines that create the “structure” in this look. Other ideas for making the look more winter appropriate include either wearing a fitted cardigan or sweater over the shirt. Don’t be afraid to tuck your sweater into your jeans; rather than looking over thought, the clean lines created by this will make you look slimmer and better put together. Short Trench Coat ($130)

Dangerous Trends

As everyone knows, not all trends are for everyone, and some trends prove to be for no one. When a trend is too innovative or ‘out-there,’ it’s usually an indication of a short life span. Witness such expired trends as destroyed jeans, 80’s neon colored fabrics, underwear as outerwear, and the list continues almost infinitely.

Other trends, however, are somewhere in the middle between completely wearable and outrageous. I call them dangerous trends because when not worn correctly, they can end up looking horribly wrong and laughable. It takes a certain type of person who is advanced in their style of dressing and is adept at experimenting with clothes.

Fur hat

Fur has been making a subtly growing comeback both among men whose goal is to be deviously provocative as well as avant-garde hipsters. While fur coats are still a long way from being acceptable to the mainstream, fur accessories seem to be undergoing resurgence in popularity. After Gucci’s Fall/Winter 2007 collection included fur accented and even three-quarter length fur coats, other designers have followed suit. Hats and scarves make for opulently warm and luxurious pieces, and can even look good when worn the right way and by the right person. The danger, coming not only from being attacked by PETA supporters, is also inherent in that you can easily look like an eccentric throwback from Stalin’s Russia or Daniel Boone.

Metallic blazer

I don’t think I’m going out on a limb in saying that this does not look good on anyone. Not only has not enough time passed since the 70’s to make this new or interesting, but the overall fashion-forwardness of it makes it too risqué for most people to wear. My theory for the existence of this trend is that after metallic handbags for women were such a hit over the summer, designers had a surplus of material they didn’t want to waste.

Slim collar

The thin-collared shirt is a style that had disappeared for a time and has now been reincarnated as the preferred shirt of hipsters (after plaid, of course). The problem with these shirts is that the collar can give a certain look of impotency, in contrast to a high collar, which can make the wearer look powerful and commanding. Therefore, it’s best not to wear them in place of a tradition shirt for any formal or even moderately dressy occasion.

White jeans for winter

White pants for winter are another sartorially tricky item to pull off. Everyone knows the dictum about not wearing white after Labor Day, but this is really an outdated and baseless rule. There are a few basic guidelines to effectively wearing this trend and not causing stares or raised eyebrows. First, white pants should never be worn when it’s gray or raining outside for the simple reason that it looks indecent and flashy. By contrast, on a sunny day, white pants can give you a ‘mod’ look when worn with black ankle boots and a striped sweater.

Raw Denim Jeans

One of the biggest trends in jeans at the moment is raw denim, referring to jeans that have not ever been treated or washed with chemicals. While at first they are stiff and almost feel like a corset for your legs, they will over time both expand and conform to your body, becoming unique to your shape.

One of the most important things when buying a pair is that they fit like a glove (a very tight one) from the onset. When you try them on, they should be so tight that it is at first difficult to pull them up. I recently bought a pair of A.P.C raw denim jeans and thought I was going to have a stress-induced stroke just trying to close the top button. The reason for this is that in just a few months, the jeans will expand and gain at very least, an inch in the waist.

When you first wear them, they feel incredibly stiff and movement itself is quite limited. This sensation takes a few months to go away completely as the jeans are broken in, but they become manageable even after the first full day of wearing them. You can speed this process by wearing them around the house and just moving in them. An important caveat, however, is that they may bleed onto light colored shoes or surfaces so you must be wary for the first few days of this.

When you have your jeans, it’s important to not wash them for least six months. During this period, they are still conforming to your body and washing them will severely interrupt this process. If they become unbearably dirty, you can have them dry cleaned or even put them in the freezer to get rid of any odor. On the A.P.C. ‘instruction manual’ that came with the pair I bought, one of the more extreme washing remedies advised, “Let your jeans get dirty for as long as possible, go swimming in the ocean wearing your jeans, rub your jeans with dry sand, and repeat several times. Rinse in fresh (not salt) water and let dry in the sun).” Besides possibly accelerating the deterioration process, I see no real world benefit in engaging in such time consuming and obsessive behavior.

If you are not the kind of person who likes neither the idea of having an instruction manual for your jeans nor having to work at getting them broken in, do not buy raw denim jeans. For those who are willing to work at it, the end result is both gratifying and rewarding. After six months of wear, your jeans will show lines and creases at natural places on your body and will tell a story about you. They will fit you better than any other pair of jeans you have ever owned previously and like life’s battle scares, you’ll be damn proud of the story behind every rip and hole in them.

I recommend A.P.C’s “New Cure” jeans ($140), which have a tapered leg and no unnecessary or pretentious markings or logos.

The Newest Trend is… ‘Timeless Classic’

If you are not a fan of the rampant lumberjack-bohemian look that has taken fashion by storm this season, you are neither alone nor out of luck. There has been a subversive trend steadily brewing that is as refined and sophisticated as the lumberjack look is common and dated.

The return in popularity of classic fabrics such as houndstooth, herringbone, and tweed has brought with it a resurgence of other timeless pieces, which together create an old-world sophistication. While never having actually gone out of style, it seemed to be in a period of hibernation, suffering through metaphorical winters of the 70’s and 80’s, only to be seen on those dandies fighting to keep alive the tradition of dressing with elegance and pride.

Spotted on the feet of Manhattan’s well-heeled (pun intended) community, are suede loafers, brogues, and boots, which are in many ways more sumptuous and versatile than the same options in leather. One of the best things about suede is that it is both acceptable for almost any office dress code during the workday and can also be transformed into a casual shoe for nightly trysts or escapades. The suede loafer, especially, is one shoe that will never go completely out of style as fashions change. The gold standard is invariably from either Gucci or Ferragamo ($590, pictured) because of their trademark hardware detailing on the shoe that gives it the extra something to complete the look. For a less expensive, though still admittedly pricey shoe, Gordon Rush ($175) makes a great pair for a fraction of the cost.

Suede boots are yet another way to show off your pre-eminent fashion ability while also impressing others with your sensibility. In the form of desert boots, like this pair from John Varvatos ($298), they are rugged and stylish in a way that a pair of Timberlands cannot be (though I still wouldn’t endorse them as a viable substitute for use in a construction site at the price by which they sell). As seen in the photo below, they can also be easily dressed up to look sophisticated, making it the only shoe that can take you from the back yard to the back seat of the company car.

Another item experiencing a renaissance, even among younger people is the patterned scarf, like this one from Loro Paina ($495). While plain, monochrome scarves are great for everyday wear, patterned ones add flair to your outfit and can even become its centerpiece due to their eye-catching design. Also in the realm of scarves, making a comeback is the silk scarf and riding on its coattails, the ascot. While neither provides much in the way of practicality or warmth, when was fashion really ever about practicality?

Leather Ankle Boots: Trendy, Stylish and Practical

One trend that has been on the steady rise this fall is the resurgence of stylish, leather ankle boots that can be worn either dressed up or casually.

The leather boot is a great item because it gives men another option between the sometimes-limited choice of either loafers or regular lace-ups. They thus add an extra flair to an outfit that says the wearer tasks risks and is confident in his style decisions.

For a dressed up look, they can easily be used as a substitute for either loafers or oxfords, depending on the suit. In general, dress boots tend to be on the side of modernity and therefore look better with equally modern suits; the slim-cut, two button styles. This pair from John Varvatos demonstrates that simplicity and restraint are the highest qualities in men’s shoes.

An easy way to wear boots more casually is to choose a brown pair. These are much more easily matched with varying hues of jeans, meaning you get more versatility and wearability. The exact same pair of John Varvatos boots in brown shows the remarkable difference that color can have on the ‘formalness’ of a shoe. Here, the handsome, marbled wood appearance makes them acceptable wear for an everyday look that would not be appropriate in black.

My favorite look is a pair of dark skinny jeans with boots and a waistcoat, which I witnessed to be a very popular look among young, fashionable Londoners last spring. It’s clearly not a look that is easily pulled off by many; a certain je ne sais quoi, rocker-chic is necessary trait for the wearer.

When buying a pair of boots, one thing to make absolutely sure of is that the end be pointed rather than round. While, a rounded pair will make you look old and patently uncool, a narrow point indicates self-assuredness as well as being generally much more fashion forward, if that’s what you are pursuing. Another thing to avoid are ‘hybrid’ boots that have laces but still try to masquerade as a dress boot, or even worse, turn into a ‘combat boot’. Pictured pair from Costume National is a heinous and glaring example of what can happen when the two very separate entities are combined: You end up looking like a combination of Hermione Granger and a suburban, gothic mallrat.