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 ($479) 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.

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Wearable Trend to Embrace Right Now

This picture, taken from the Mulberry website, showcases the look of this season. The leather bomber jacket, the plaid shirt, braided belt, and slim dark-wash jeans are all integral pieces for anyone looking to follow the latest trends. Even with the plaid shirt, however, I would not classify this look as “bohemian intellectual.” Rather, the slim-fitting bomber jacket and jeans provide a structure to this look that is more the Ramones than Woody Allen.

With the exception of the braided belt, this is a look that won’t soon go out of style. Every man should have a bomber jacket in his closet. They are great for a casual night when wanting to add an element of timeless cool to your outfit and for staying warm well into the winter. When buying one, you should look for a style that is cut close to the body and ends right below your belt. If the jacket is too small, it will look effeminate (as is almost the case in the above picture). This one from Dolce and Gabbana ($1,395) fits perfectly and also has an immaculate style that will still be cool in thirty years (which is almost enough time to justify the price).

For the belt, the trick is not to just find any old, braided variety. Previously existing only in the realm of grandpa fashion, design houses from Prada to Balenciaga gave the braided belt a much-needed reworking, making them wider and sturdier. This one from Diesel ($70) is one of the coolest and most stylish you can buy. It has a distressed looking front with the rest in braided leather, clearly distinguishing it from your father’s golfing belt.

Despite my avowed detest for all things plaid, I surprisingly don’t find this shirt terribly odious. The red, white, and gray color scheme keeps it simple and not looking too much like a tablecloth pattern. This one from J.Crew ($50) is almost identical in pattern. Just be wary that a bad pairing of plaid and leather will leave you looking like one of the Village People.

In the spirit of this outfit, a pair of boots would be a great addition to pull the look together. This pair from Mezlan ($149) are both affordable and undeniably stylish. The subtly Western look brings another dimension to your outfit without being overwhelming or tacky. When wearing slim jeans, make sure that the leg of the jean goes fully over the boot instead of tucking it in, which cannot be done without looking like the guy who’s trying way too hard.

For a pair of dark jeans, refer to my article about the season’s best jeans.

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Mastering the Rumpled Look

Cooler weather is always more kind to men when it comes to getting dressed in the morning. We can layer, pull out the cords, throw on a chunky jacket and top it off with a warm scarf. The sheer variety of cool weather clothing is something many a man looks to as the thermometer drops.

For those of us with the flexibility to move between business dress and corporate casual, what I call the “Rumpled Look” is a middle alternative to just dressed up and dressed down. Originally an offshoot of the American Preppy aesthetic, the rumpled look has come into its own.

The basic idea behind this style is the allusion to old money, classic taste, and timeless style. Newer or continental styles don’t lend themselves to celebrating beat up and handed down clothes quite like the preppy culture does. The unspoken message of the slouchy khakis, un-ironed oxford shirt and slightly beat up shoes is that you have old money, an Ivy League education, a summerhouse in the Hamptons, and you sail a lot. Or at least you dress like you do.

I have to say that this really is a fun look which is not hard to carry off well as long as you don’t try too hard. Like the current “critter” trend, with pants, ties, belts and coats are adorned with embroidered animals and icons of every sort – dogs to martini glasses – less is more. One creative article of clothing at a time is ironic, more is overkill.

For most men, wearing this look at the office can be a bit tough, but depending on your company’s culture, distressed chinos matched up with a wrinkled button down under a crewneck sweater should be just fine. For a younger look, don’t tuck in the shirt but rather let it hang out under the sweater. Wear a washed tweed jacket over the whole outfit. This kind of layering effect is another signature of the rumpled look. To meet up with friends for drinks, try pairing a permanently wrinkled Thomas Pink dress shirt with dressy jeans and a sport coat. The juxtaposition of classic and casual is a key balance to this look.

Like any other style you want to incorporate into your own, stop and look in the mirror before leaving the house. You want to be happy with the overall feel and proportion of your outfit. The goal should be to look like you’ve had everything for years and don’t think twice about getting dressed.

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Turn Lumberjack Style into Bohemian Intellectual Look

It’s no secret that fashion run in cycles and things that were once fashionable will almost always come back in style. It is nonetheless a little sad and disheartening that truly atrocious styles can’t be weeded out for good. When the seventies were over, I believe it was the general consensus that the Village People-lumberjack look was over. Not so, apparently.

Though not an exact copy of the late 70’s look, the lumberjack style has been reincarnated as what I would call a “bohemian intellectual look.” Making their way back into not only the pages of GQ, but also quickly spreading into the streets, are bootcut jeans, plaid shirts, corduroy jackets, and oversized sweaters.

This is a clear departure from the past few couple years of structured pieces and slim cut jeans. The worst perpetrator of this style has been J. Crew. Because of its accessible prices, it has been able to promulgate among the masses.

I have never liked plaid so I am clearly biased against its resurgence. The entire grunge look of the 90’s was a dark time for style. I believe that it set the stage for an entirely new level of lower standards when it came to dressing as grunge was, in a sense, a repudiation of fashion.

To be fair, I think there is a way to embrace the trend in a classic way that exudes “weekend at the country manor” rather than hipster punk. Tartan does, after all, possess a rich history dating back to Braveheart days. Shawl collar and toggle close sweaters are two ways of interpreting the style in a positive way.

Another decent aspect of the “bohemian intellectual” look is the importance of layering. This means that you shouldn’t get rid of your cardigan just yet. One good approach of making this work in the dead of winter would be to wear a down vest over a shirt and cardigan, then finish with a close cut overcoat. I like the contrast of new and old this creates. For a discreet nod to the plaid trend, you could include a tartan scarf from Burberry or elsewhere. As for the bootcut jeans, I recommend staying away and opting for just straight leg jeans, which are a compromise between skinny jeans and flared ones.

With this trend, you can also expect to see more clothes in earth tones and a move away from black and gray. The shoe of choice to match would be a moccasin unless you are actually going to be at your country manor, in which case may I suggest the Hunter rain boot (pictured).

If you are in a lumberjack mood, J. Crew is currently having a fall sale where you’ll be able to stock up on enough plaid to clothe an entire Irish village.

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Americana Look: The Urban Cowboy Trend

It is rare that I applaud fashion. Style is far more important to me than trend, and it is to that Pantheon of style icons that I pay homage. As Oscar Wilde once said,“fashion is a form of ugliness so intolerable that we have to alter it every six months.” It is that unappealing temporary charm that puts me off fashion; that risk of buying something which will be worthless in half a year. I am never a slave to fashion.

However, fashion has its moments. They are rare and fleeting, but they are there. Once in a while it learns to provide practical style which will last from season to season, year to year. One particular autumn and winter trend has been the Americana look; checks and plaids, sport shirts, corduroy and cosy thick weave scarves. “Nothing” you may cry, “that hasn’t been in GAP for the last ten years!” Perhaps you are right. Perhaps there is nothing that revolutionary about the look, but does there need to be? It’s just something that fits so very well with the cold season. Cosy materials, patterns echoing a bright practicality, and accessories galore make the look thoroughly appropriate for the coming months.

Plaid and denim

One of the most comforting things about this look is that you can relax in the clothing without fear. It is a very casual look and the less contrived and the more ‘lived-in’ the outcome the better. Denim does not have to be skinny, dark and straight. In fact, the best denim to wear with this urban cowboy uniform is washed, old looking denim. The dark and shiny Dior Homme jeans are not appropriate – the plaid and denim man has to look like he cares less about the fineness of threads and more about unswept leaves on the driveway.

Boots and coats

Plaid shirts and college-style blazers and cord jackets are very charming in a New England way. However, the key to the outback dandy’s image is the lack of formality. Lapels begone! Big chunky coats are a central part of this look. Hacking jackets and duffel coats offset the hick charm of plaid and check and keep the palette under control; their versatility allows for multiple layering.

Footwear should be carefully considered also. The urban cowboy has no need for Wellington boots, but practical shoes and boots with a Commando sole do work well and are very comfortable for cold winter days. They also help to promote the casual weekender appeal of the look.

Scarves and hats

Scarves for this look are big and chunky. No skinny scarves or delicate silk here. A man needs a scarf that looks almost childlike in its naivety. Huge weave, snake-like creations and tartan are the key trends for scarves. If wearing tartan, avoid wearing with too many checked or plaid items – overkill would be a shame.

Hats are important for the urban cowboy. He likes to be outside, it reminds him of being at home on the range, and he needs some practical headgear to keep his ears warm. Beanies, woodsman caps and driving hats are the order of the day. Nothing too elaborate, just a little nod to design by incorporating a houndstooth or check pattern.

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