Dress Like a Man (20 page)

• Suit trousers
  are exactly what they sound like. If you have a jacket, and there are accompanying trousers made from the same fabric, those are suit trousers. Nearly all are the same style as dress slacks, and can potentially be worn as such without the accompanying suit (but be careful not to overwear the trousers to the point that they fade more than the jacket).
  
• Dress slacks
  are evocatively named: they hang slack, with a smooth drape all the way down. Most are made of wool, though it's not required. The style is simple and elegant, with pressed creases, slim waistbands, and unobtrusive pockets. Most are high-waisted, and many come with tabs for suspenders.
  
• Khakis
  get their name from a tan color, but these days manufacturers use the term for any sturdy, straight-legged cotton twill trousers, regardless of the dye. Earth tones are still the most common shade. Khakis usually have pleats and cuffs, and are sometimes made more casual with the addition of cargo pockets on the thighs.
  
• Chinos
  are lighter than khakis, have tapered legs, and are usually plain-fronted rather than pleated. They are also less likely to be cuffed, although there are certainly chinos with cuffs out there. Of the two, chinos are a touch dressier -- depending, of course, on color. Lime green chinos are less formal than plain tan khakis!
  
• Jeans
  should be familiar to almost every man: sturdy denim work clothes, usually in blue. The darker the shade and the closer the fit, the dressier the jeans. You can wear dark, fitted jeans with blazers and even suit jackets, while lighter blue jeans are better off as casual and manual labor clothing. Jeans typically sit lower on the waist than other trousers.
  
• Cargo pants
  are loose-legged trousers with buttoning flap pockets on the fronts (and sometimes sides) of the legs. In any material, they're a casual style, and should only be worn for practical purposes.
  
• Overalls
  follow the same rule as cargo pants: practical clothes only, usually for messy manual labor. Don't bother trying to make a style statement with them.
  
• Shorts
  are usually not the most flattering option for a man. Only wear them in very casual social settings during the hottest months. If you do wear them, they should fall somewhere between halfway down your thigh and the tops of your knees -- never far enough to cover the knee, and never more than halfway up the thigh. It's a narrow window. When in doubt, wear lightweight, breathable trousers instead.
  

Your trouser selection is going to depend a bit on your work needs and your personal style, but broadly speaking most men will own at least one or two pairs each of jeans, khakis, chinos, and slacks.

At the very least you want to own one good pair of gray wool slacks and one pair of dark, fitted jeans. Both are "go anywhere" sorts of clothing -- they can dress up or dress down easily, and they pair well with almost any style of shirt or jacket.

C
HAPTER 28:
M
EN'S
S
HOES

Of all the specific clothing items we discuss in this book, men's shoes might be the most
underrated.

Very few men give footwear enough credit for its ability to make or break an outfit. The right shoes -- poetry. The wrong shoes -- disaster.

Part of that may come from resistance to the price of shoes. Good shoes, like a good suit, cost much more than modern consumers are trained to think of as "reasonable." You're looking at easily $100 for a basic pair of leather dress shoes; more like $2-300 for anything unique or special. And that's just for decent off-the-rack shoes -- any kind of custom construction will be even pricier.

Business Dress Shoes

The highest-formality footwear most men will wear in their lives are black balmoral Oxfords. 

The two names are used somewhat interchangeably by retailers these days, although "balmoral" technically refers to a construction style, while "Oxford" originally denoted the height of the shoe (low on the ankle). Nowadays "oxfords" is often used to refer to any dark dress shoe, and "balmoral oxfords" to the most formal versions.

Regardless key feature here is what's called a
closed lacing system:
the small pieces of leather with the eyelets are stitched directly into the uppers, rather than atop them.

It sounds more complex than it is. If the laces are threaded through separate, distinct pieces of leather that lie on top of the body of the shoe, it's an open lacing system, and it's not a balmoral. If the top of the shoe is a single, smooth level, it's a closed lacing system.

For maximum business formality, go with a plain black balmoral oxford, polished to a good shine.

Leather Shoe Styles

Beneath the black balmoral oxford lies a whole range of leather shoe styles. These should, ideally, be the bulk of your shoe collection, with only a few pairs of rubber or cloth shoes in there for specific practical purposes. 

The following list is arranged loosely in order of formality, from most formal to least, but understand that there is a great deal of variety here. A sober, dark pair of work shoes can look more formal than a flamboyant pair of wingtips. It all depends on the colors, the materials, and what the shoes are being worn with.

Think of all of these as flexible, interchangeable options, and build a collection around the ones you like most:

• Balmorals
  - In addition to the plain black dress style, balmorals with small decorations like broguing or cap toes can be worn with suits to give a slightly more relaxed impression. Men who wear suits on a regular basis will likely want to build a collection. In colors other than black, the style becomes much more relaxed, and pairs well with slacks and sports jackets.
  
• Blucher/Derby Oxfords
  - A closed-toe, low-ankle shoe with an
  open
  lacing system rather than a closed one is called a "blucher" or a "derby." Traditionally, these were not business shoes, but they've gained acceptance, especially in America. (Indeed, most stores sell more open-lacing dress shoe than proper closed-lacing balmorals). Relaxed suits, especially those in brown and light gray as opposed to the more formal dark colors, go well with simple bluchers.
  
• Dress Boots
  - Take a balmoral and extend the height up past the top of the ankle, and suddenly you have a dress boot instead of an oxford. These can be quite dressy -- just a shade less formal than their low-ankled cousins. Plain black styles are an excellent winter/snow option for suit-wearing men who don't want to bother with galoshes or shoe changes every time they step outside.  
  
• Brogues
  - Decorative hole punch patterns in the leather uppers of a shoe make it a "brogue," regardless of construction. Most brogues are blucher-style. They're a versatile style: as long as the patterning isn't too overwhelming, dark leather brogues can go with anything from jeans to dark slacks.
  

• Wingtips
  - Sometimes called a "full brogue," these have a cap toe with wings that sweep back around the edge of the shoe. The cap and wings are decorated with perforations, and are often a different color of leather than the uppers. The two-tone variety are more casual than monochrome wingtips, but all of them are better suited to dress-casual wear than business attire. 
  
• Loafers
  - Smooth leather slip-ons, often but not always decorated with a buckle, leather band, or tassle across the top of the uppers. Simple black loafers can be worn with suits, but most are designed for more casual wear.
  
• Bucks
  - Bluchers made out of buckskin, which has a distinctive rough surface that makes it look a bit like suede. The "white buck," made of white buckskin with white rawhide laces and a light-colored sole, is a traditional Southern style that often accompanies seersucker pants and suits.
  
• Chukka/Desert Boots
  - Low suede boots with crepe rubber soles and a small number of eyelets for the laces (generally four per boot). Classic relaxed footwear -- if you're looking for an easy upgrade from sneakers, chukkas are a good starting place. They can dress up to business casual standards in a pinch, but are mostly a social style.
  
• Western/Cowboy Boots
  - The American icon. Not for the stylistically faint-of-heart. In some Western states you'll get businessmen pairing them with suits (especially well-to-do ranchers and oilmen), but most of us should stick to jeans when we wear cowboy boots. Limit the number of other Western accents in the outfit, unless you're actually going to a rodeo or a line dance -- you want it to look like a style, not a costume. Dark jeans, a plain white dress shirt, and a black or charcoal jacket go very nicely with Western boots.
  
• Saddle Shoes
  - A two-tone style with a "saddle" shape arched over the center of the uppers. Not all are leather -- shiny sneaker style saddle shoes have come in and out of fashion over the years -- but the best-looking ones are suede, preferably in two muted colors. They're a casual, social style, and not meant for business wear.
  
• Boat Shoes
  - Also called "topsiders" and "boaters," these are leather slip-ons with textured rubber soles. Most have one or two pairs of eyelets and leather laces, but the shoes stay tied, and are pulled on and off like loafers. They're a classic summer style, well-suited to wear with khakis and lightweight slacks. Don't wear socks with them.
  
• Work Boots and Work Shoes
  - Identical except for their height, these are a balance of style and practicality: tough leather uppers attached to plain rubber soles with a Goodyear welt (accept no substitutes on the latter point). The less contrast you have, the more formal they are: black boots with black laces and soles can dress up pretty far for work clothes, whereas brown boots with black soles and yellow stitching and laces are definitely job site (or rock concert) attire only.
  
• Sandals
  - If you're going to wear sandals, they should have leather straps and a simple design. "Sport sandals" are, of course, totally appropriate if you're going rafting or something along those lines, but for more relaxed activities -- even ones that happen near water -- class it up a little.
  

Non-Leather Shoe Styles

It bears repeating: most of your shoe collection should be leather (the uppers, at least). The difference between a nice outfit with leather shoes and a nice outfit with sneakers is massive.

Cloth and synthetic shoes should mostly be saved for the practical settings for which they were intended: gyms for gym shoes, and so on.

That said, there are a few cases to be made for wearing casual shoes as part of a conscious style:

• Canvas Sneakers
  -- The Converse All-Star is the iconic example here, but there are plenty of more updated looks in the same general family. They're obviously not business attire, but a brightly-colored pair can be a great way to jazz up a social outfit if you're worried about looking too stiff or frumpy. Red sneakers, blue jeans, and a white shirt with a dark jacket is such a classic funky look that it's almost not funky anymore (but it's still a good one, don't worry).
  
• Espadrilles
  - At a distance these hemp-soled slip-ons look a lot like canvas sneakers. Some even come with laces, making them harder to tell apart. Treat espadrilles like slightly dressed-up All Stars: a good way to add some color and casual "cool" to an otherwise ordinary outfit. Go easy on pairing them with other brightly-colored or exotic clothing pieces.
  
• Gym Shoes
  - Rubber and synthetic sneakers aren't usually fashion items, but there are a few specific demographic niches where they're status symbols. If you know you're traveling in circles that are likely to be impressed by $500 Nikes, maybe they're worth buying and wearing in social settings. For most of us, however, gym shoes should be worn at the gym, and nowhere else.
  
• Slippers
  - Worth mentioning while we're on the subject of footwear. Own a nice-looking pair that you can wear around the house when you have guests over. It's classier and warmer than going barefoot, and easier on the floors than wearing shoes inside the house.
  

Men's Socks

The default rule for socks is to match them to the color of your trousers.

It's a good rule. It's simple, elegant, and safe. You'll never go wrong doing it. The goal is to avoid making an awkward break in your look -- you want eyes to move up from your feet past your trousers and all the way to your face without getting hung up on something weird-looking about your ankles.

Matching the sock color to the shoe color is a
distant
second-best strategy. It's better than a total mismatch, but not by much. In some cases it's almost counter-productive -- if you've got trousers that are lighter than your shoes (medium-gray slacks with black dress shoes, for example), dark socks are going to look jarring against the trouser cuffs.