Back to Basics - The Shoe

In this age of doing more with less, global energy crises, and the Ugg viral outbreak, it is the perfect time to contemplate how many shoes a man should own. The Thoughtful Dresser states a rule, unfamiliar to this writer, that a man tends to believe he doesn’t need more than three. The esteemed Manolo places that number closer to ten. The simple answer is - as many as he wears.

Most men treat footwear as an afterthought, which naturally risks derailing even the most carefully considered outfit. Before even thinking about tie and shirt combinations a man should take stock of what is going on his feet. As a learned friend from law school once opined about two thuggish young men wearing impeccably maintained kicks, “gangster starts from the ground up.”

The following list does not take into account footwear that is work specific.

Black Leather Shoes

Nothing works in more situations and paired with more outfits than black leather, whether lace-up or slip-on. Avoid the risk of looking too corporate by going with a more playful option, such as Barker Black’s loafer.

Brown Leather Shoes

First of all, we can stop calling leather shoes “dress shoes,” as though they should only be used when one is trying to make some sort of impression. If you find yourself dreaming of leaving work so you can take off your shoes, chances are you’re either not spending enough money or are buying the wrong fit. I’ve never understood the logic where you buy five shoes, none of which feel right, instead of spending the same amount on one pair that can last ten years. If you already have a pair in black, a brown pair can give new life to suits and, I am lead to believe, can even be worn without socks in the summer.

Casual Shoe

Running shoes are called running shoes because you exercise in them. If you’re wearing them with jeans and a blazer, you are doing them a disservice and causing an existential dilemma. If you’re not going to travel the white leather oxford route, you need a pair of casual shoes that don’t look like you’re headed to the gym.

I’m probably biased as I own five pairs, but for my money Medium makes some of the best looking casual shoes around. I have two of the Expressionist in different colorways.

Are there any shoes that a man should never wear? In Vancouver, apart from the aforementioned Uggs, the ubiquitous socks with sandals combo is a frequent offender.

However, I would argue that any three strap sandal tends to make men’s feet, already big and plodding, look like trussed up legs of ham. Which, unless you’re a Roman gladiator, never ever looks stylish.

The Handkerchief as Tie

Men rarely get to wear silk without appearing foppish.

So it’s a shame that so many decline to wear a tie. It is pretty much the only opportunity a man has to decorate himself with a length of patterned silk.

Some prefer not to wear a tie because it seems uncomfortable. Others because they associate it with school or with dull, office work (the ‘noose of the Man’). Still others dislike wearing one because it appears too formal – in an old office of mine the appearance of someone in a tie was always greeted with the question “got a meeting today?”

Now if wearing a tie is uncomfortable, your shirt is probably too small. But there’s nothing to be done about the psychological scars of school days or a hatred of the Man. I would suggest instead the addition of a silk handkerchief in your breast pocket.

A good guideline for wearing a handkerchief is to think of its colour in the same way as you would that of a tie or a shirt. If it is there for background, for reinforcement but not to catch the eye, then go for a plain colour picked out from the rest of the outfit – blue or white from your blue or white shirt, for example. This is nearly always the best option if you are also wearing a tie, but may also be useful if you already have a surfeit of pattern elsewhere.

The alternative is to treat the handkerchief as a tie. This is where it gets fun. Select your blue serge suit and a pale blue shirt, and then pick out a handkerchief with the same colour harmonies in mind as with a tie. A burnt orange pattern might go well, or perhaps a dark, paisley purple. Pale green can go well with the right tone of blue, and a patterned burgundy will look smart.

If you feel conformist one morning, opt for a sharp white cotton square. If you’re feeling a little crazy, select a pink foulard handkerchief, overflowing from the breast pocket.

The handkerchief is the replacement for the tie. It is the same opportunity for decoration, shifted across your body and stuffed in a pocket.

Your neck is free and it’s unlikely you look like a schoolboy; yet you have retained that avenue of expression. You look smart, perhaps even more conservative; yet you can still wear silk.

Commuting Bags

For quite a while I’ve wanted to write a follow-up to my “Defending a Man’s Bag” article, one of the most popular I’ve written. Well, here it is and I now suspect that these updates will be an ongoing project. As I am now expecting my first child, due sometime this summer, the bags I carry will soon serve a totally new purpose. I now have to reevaluate their functionality with new eyes. I’ll be moving around not only with my own stuff, but roughly a ton of baby supplies as well.

This got me to thinking about the kinds of bags best suited to commuting, an equally daunting task usually measured by how hard it is to get home should something be forgotten. The further away from home base equals the amount of stuff you stuff in the bag.  When I speak of commuting here, I’m excluding those of you who travel by car. You don’t factor into this one; just those (me included) who must tote their worldly possessions slung over a shoulder day after day.

Currently, I have an olive drab Jack Spade Day Bag that I use for day to day commuting. It’s essentially a small messenger bag, perfect for a book, wallet, agenda, mobile phone, Blackberry, etc. It’s simple and neutral – fine for business related travels. The problem is that I also have a laptop with me every day and with that added to the mix, the Jack Spade bag is too small.

So, I actually carry two bags.  The laptop goes into an ever changing variety of other bags – currently a very cool helmet bag from Flyboys.com, a supplier of armed forces pilot gear. It’s light and has a great military feel to it. As it’s designed to hold a fighter pilot’s helmet the bag is also cavernous. It was inexpensive and meets my needs for an informal commuter bag. Namely, it carries a lot without being bulky, has a good number of well placed pockets and is very durable. All key points for a good commuter bag.

That said, I really need a single bag that does it all. In a few months I’ll have to pare down to only one bag so it better be a good one. It needs to act as a classic “man bag” and hold all the stuff I need every day (which will now include spare diapers, bottles, etc.), as well as a business bag that can handle a laptop, files and other work materials.

The other issue is that when it is loaded up, there should not be any physical discomfort; no shoulder strains or aching back. Oh, and it needs to have some good, classic styling that can take me from errands to office.

How hard can that be?

I’ll let you know, because over the next month or so, I will be searching for that elusive commuter/dad bag and will report back on my findings. After some preliminary scouting a few have come to my attention.

Jack Spade (no, I’m actually not a paid endorser) has a pretty good version in the “Field Bag.” He also produces a specific dad bag, but so far as I can tell, it’s just a Field Bag that comes with a changing pad.

On the casual side, Timbuk2, the classic messenger bag maker, also has a good option with its large original messenger bag. The great thing about this brand is that you can choose your own colors when ordering online.

Of course, if you don’t want to carry a shoulder mounted bag, the granddaddy of classics is the LL Bean Boat & Tote. Perhaps one of the simplest yet versatile bags, it has achieved iconic status for many folks.

Whether you are looking for a basic everyday man bag, a commuter bag, or a dad bag, the same rules apply for all. It should meet your functional needs, be sturdy, have enough interior pockets to keep things organized, and have a distinctly masculine look to it.

I’ll let you know how my search goes and let me know if you have any suggestions of your own.

The Appeal of Nautical Look

On a recent sojourn to the south coast, walking along the shore in the shadow of the chalky and savage cliffs, I rediscovered my connection with the sea. It was not a particularly fine day and nor was it a remarkable stretch of coastline, but it was the utterly romantic situation; gazing out to a wild, unforgiving open water standing at the meeting place of land and sea, salt water spraying onto my face and a quite incredible wind that made me feel glad for my warm hat and high-collared coat. I was surrounded by the elements, isolated from the comforts promised by the distant lights of cliff-top homes and it was a remarkable feeling.

I have often envied those living the nautical life; back and forth on ocean going vessels, pacing down teak decking, the bobbing up and down, and the quiet summer evenings anchored in quaint harbours with a front row seat of the twinkling onshore lights. Nautical people seem never to forget the sea; it never leaves them. You stay on water long enough and you’ll probably have salt water running through your veins.

The British have long been a seafaring people. It’s a hefty weave of the rich tapestry of our island that we have always built ships and have always spent a significant amount of our time, for work or pleasure, moving about on them. And it is perhaps because of this heritage that I feel a warm connection to all things nautical, especially the nautical style of clothing.

The nautical look is a fashion that can be traced back to the mid-Victorian period, when a portrait was produced of the young Prince Edward, heir to the Empire, in a sailor’s outfit. Although it was merely a miniature version of the outfits worn by ratings on the Royal Yacht and not at all a serious expression of fashion, it became a wildly popular choice of children’s clothing by the end of the 19th century as parents were obliged to emulate the whims of the royals.

The ‘sailor’s fashions’; once connected with the coarse and unrefined ship hands, had become a vogue for young people the world over and it would not be long before Coco Chanel turned the classic merchant navy simplicity of colouring into a complex range of fashions displayed in her Deauville and Biarritz boutiques in navy, white, splashes of red and stripes; it was simple and yet elegant.

Nowadays, gents are as likely to dress like a sea captain as they are a lumber jack from the forest or a lounge-lizard from Knightsbridge. It is an accepted style, and what a style it can be. With blue striped jumpers under pea-coats, crisp navy double breasted blazers, white trousers and smart canvas shoes, ‘nauticising’ your look could never be simpler. The colours are wearable and classic and the lines are forgiving to men of all shapes and sizes; I think one would be very hard pushed to find a chap who views navy blue as a dangerously experimental colour.

Keeping the ‘detail’ to a minimum is important; no stitched-on anchors or captain’s hats. The homage to the sea should be done, and easily can be done, tastefully.

Changing Your Pants: Dressing Up

I am feeling a little vindicated today because it seems dress and casual pants, long the forgotten stepchild of designer jeans, are making a comeback. As retail sales for men’s jeans are finally starting to slip, corresponding numbers for dress and casual trousers are actually rising. This shift is being blamed on a combination of supply and demand – there is a glut of denim in the market and not enough buyers – and that men are showing more of an interest in dressing well.

While the market most certainly is saturated with too much denim, I personally think that the latter argument, that men are more interested in dressier looks, is the real culprit. As I have mentioned before, I think menswear is growing up and growing out of, “all casual all the time.” Guys want to dress well and look more put together. As a friend of mine recently said, to stand out as an individual these days, you need to dress up. The blue blazer as social rebellion – go figure.

Trousers are a key way you can give yourself a more polished look and the trend toward better dressing only helps. The hybrid versions of dress trousers that have been an industry focus – like five pocket khakis modeled after jeans – are giving way to sleeker and traditional dress trouser styles. Flat fronts with pockets that are either on seam (the pocket opening is literally on the pant leg seam) or besom (the pocket angles slightly forward off the pant seam) are the formats of choice.

Another issue centers on how the pant bottoms are finished. The best option in my opinion is open bottom pants, meaning the hems are unfinished and can be properly tailored to your body. Closed hems are the pre-fished pants that you grab, go, and hope will work. While convenient, if they do not fit you just right, the pants will look either too short or too baggy. In the casual category this is not an enormous issue, but when it comes to dressier trousers fit matters.

This leads to an obvious fork in the road: are most men – at least those who now want to dress better – ready for the tailor? It can take time, cost money, and delay the instant gratification we are so used to these days. But I think the payoff of well tailored clothes makes a huge difference in both your overall wardrobe and in how you feel and carry yourself. If men are ready to dress up a couple on notches then they are probably ready to invest some time and money in making sure those new clothes are worth the investment.

I am under no illusion that everyone is about to start sporting suits and trilbies every day of the week, nor would I want to see such a thing happen. I am confident however, that we are turning a sartorial corner.

As I mentioned in an earlier column, the Dot Com bubble which imploded many people’s retirement accounts also ended the “suit-as-anonymous-uniform” rule. The resulting casual work wardrobe movement has now reached its predictable nadir and guys are wondering why they all look shapeless and generic. The “return to dressing up” that DNR somewhat pans in a recent article on this very subject, is not a return to the past but rather a rich and varied exploration of the clothing, quality, and stylistic opportunities that we simply did not have before.

Just look around at the renewed attention to tailored clothing, fabrics, bench made footwear, fine leather goods, and luxury mechanical watches. To me, it’s not so much a return to dressing up or even an obsession with luxury as it is a shift toward new opportunities in personal expression and a celebration of quality and uniqueness in an increasingly homogenized world.