Casual Shoes

You have many styles to choose from for casual shoes, from more stylish and formal monk strap or semi-brogue oxfords, to desert boots, boat shoes, moccasins, espadrilles, and canvas sneakers (Converse or Vans).

Choose a style or two that fits your lifestyle, but remember, to exude 007’s class, you’re looking for something that leans more toward the classy side like dress boots, dark leather or suede desert, Chukka, or Chelsea boots or boat shoes, and less towards the super-casual side like All-Stars, espadrilles, or sneakers.

Workout/running/tennis/basketball shoes should be relegated to sport and exercise use only. As noted below, the jeans or shorts with athletic shoes look is distinctly American, and neither classy or tasteful (yes, even if they're $200 sneakers).

Belts

Your shoes and belt should match, or at least complement each other. One of the biggest and most common mistakes of men all over is wearing a black belt with brown shoes, or a brown belt with black shoes. It is a good idea to purchase a matching belt whenever you buy new shoes. Make sure the hardware on your belt matches or compliments the rest of the metal in your wardrobe.

Dress Shirts

For the purposes of looking like a gentleman spy, we’re only covering dress shirts as button downs.  While sport shirts may be fine for many, they aren’t as slick and don’t exude the class you’re looking for.

You’ll probably end up wanting a variety of dress shirts, starting with a couple of white versions, then light blue, before branching out into patterns and more ostentatious colors. Remember from The Suit section: flat front, no pockets, no button down collars; you want clean and refined.

Polo Shirts

The fitted polo shirt is the gentleman’s alternative to t-shirts. Worn with everything from jeans to khakis to dress slacks, they are versatile and stylish.

Leave the baggy shirts for the kids; the look we’re going for here is a quality fitted version (generally referred to as slim, custom, athletic fit, etc.). Ralph Lauren, Lacoste, and Sunspel the standouts in this group, with Sunspel having the distinction of being worn by Daniel Craig as 007.

Cotton isn't the only choice anymore, and there are excellent choices like merino wool or other performance fabrics.

Sweaters

When the weather gets cool, a quality sweater — especially cashmere — is a great investment. Crew neck or V-neck is your choice, but if you’re looking to wear one over a dress shirt and tie, opt for the V-neck. Worn alone, over a dress shirt, or underneath a blazer or casual jacket, the cashmere sweater is an essential piece of the gentleman’s winter wardrobe.

T-shirts

Ditch the loose, faded, graphic tees, and replace them with quality, well-fitting plain t-shirts. White, gray, and black are good multi-purpose choices that can dress down a pair of slacks or be dressed up with a jacket on top. Like the polo shirts, cotton isn't the only choice anymore, and there are excellent options in merino wool and other performance fabrics.

Slacks

Gray, navy, black, khaki; flannel, wool, cotton. Good slacks should make up the bulk of your trousers selection. Pants should never be the focus of your wardrobe — they should draw the eye up to your jacket, or down to your shoes, not be the center of attention. They should be flat front, with no cuffs, and should fit perfectly.

Buy several pairs, selecting from gray flannel, navy wool, and various shades of khaki (going from very light tan, to olive). You’ll find yourself wearing some colors very frequently, and some less often — donate the unworn pairs to charity and buy more of the same couple of basic colors that will become the staple of your wardrobe.

Jeans

Blue jeans are iconic, stylish, versatile, and durable. Every man is well served to have at least a pair or two but put in the time to find the perfect pair.

Your focus is first and foremost on fit — take the time to try on different styles and different manufacturers to see what works. Keep in mind that the most universal style is usually a straight fit (neither tapered or flared at the lower leg) with a regular or slightly lower waist (but not low-rise or skinny jeans).

After finding the perfect fit, select the right color. For most men, you should start with darker colored jeans with no pre-distressing. Dark jeans can be dressed up with a dress shirt and sports jacket, or dressed down with a t-shirt, but lighter colored jeans and distressed fabrics/styles are for casual wear only. A good idea might be purchasing a perfect, dark pair – as they start to wear and fade with washing, buy another pair for dressier use, and relegate the older pair to more casual use.

Swim Trunks

If you’re living the Gentleman Spy lifestyle, you should be hitting the water and the beach, which means you’ll need a good pair of swim trunks. While the spandex Speedos or long, baggy board shorts may be fine for some, they’re not ideal for almost anybody.

There are many options, but the standout in swimwear is Orlebar Brown. With shorter and longer styles, their cut is perfectly tailored to the athletic physique, they are exceptionally styled, and are the choice of Bond himself.

Other good choices include Frescobol Carioca, Mackeene, and Vilebrequin who all offer fitted suits in varying lengths to suit any man's body and style.

Navy Blazer

Tracing its origins to British naval traditions, the navy blazer is another classy and versatile piece that is at home in many different environments.

The traditional fabric is wool, and the blazer is traditionally adorned with brass buttons, though many modern men are opting for buttons made from plastic, horn, or mother of pearl, colored to match the navy color of the fabric.

While other styles are available, you are looking for a single-breasted, two button jacket with notched lapels — the double-breasted versions are too formal to be of much utility, and are generally only applicable to the older (old age + old money) crowd.

Overcoat

Those in warmer climates may be able to do without an overcoat entirely, but if you live in temperate climates, the overcoat allows you to stay well-dressed and looking sharp in the coldest of weather.

There are many styles to choose from, but you’re looking for a coat that is long enough to cover your suit jacket with some room to spare. Wool is the material of choice as it is sturdy, warm, relatively water-resistant, and goes naturally with suits and blazers or sports jackets. Dark, solid colors like gray, navy blue, and black are good choices here.

Pocket squares

Not to be confused with the functional handkerchief which should be kept discreetly out of sight, the pocket square is decorative and worn in the left breast pocket of the suit. This is an excellent way to add color and uniqueness to an outfit. You should have a few pocket squares in white, and other colors as you wish. These are to express individuality and compliment the rest of the outfit, not to stand out on their own, so don't go overboard with these.

Leather gloves

Like the overcoat, these might not be necessary for those in warmer climates, but they are a necessity for many.

You are looking for good quality leather, generally matching whatever other leather you happen to be wearing – black gloves for black shoes, brown gloves for brown shoes, etc.

Light insulation provides good three-season utility, but those living in very cold climates may need an additional pair with heavier insulation as well.

Worn/Faded/Stretched/etc. T-shirts

Worn, old, stretched, faded, outdated, etc. t-shirts should not be part of your normal wardrobe.

High quality, well-fitting t-shirts are fine for super-casual wear, but to really look your best, you’re generally better advised to step up your game a notch and move up to a polo shirt or button-down.

Ball caps

Most of the world doesn’t wear ball caps. This is a distinctly American phenomenon except for urban youth elsewhere who mimic what they’ve seen on American rap videos. Don’t be that guy.

Caps are fine for sports, when they're part of a uniform, or when they're a necessary accessory like a shooting course or being out on the water fishing. They should not be a staple of your daily wear if you're trying to upgrade your style.

Running/workout shoes with jeans

At the very least, you should have something like espadrilles, moccasins, boat shoes, or Chuck Taylor's/Vans.

Sneakers/tennis shoes/running shoes are for sports only, not for spending a day on the town.

White socks

White cotton crew socks are a staple of almost every American man’s wardrobe. They should not be.

Go to your closet or dresser, take all your white socks, and throw them away.

Replace them with wool socks that match the colors of your pants. You can have thicker socks for winter, finer pairs for dressier occasions, and padded pairs for hiking or skiing, but white cotton socks have no place in a man’s wardrobe. Ever.

Shorts (especially baggy/cargo shorts)

Shorts may be gaining popularity elsewhere, but they are still primarily an American faux pas. In much of the rest of the world, shorts are viewed as children’s clothing. From Tom Ford, the man who suited Daniel Craig from Casino Royale to Skyfall: “A man should never wear shorts in the city. Flip-flops and shorts in the city are never appropriate. Shorts should only be worn on the tennis court or on the beach.” This goes especially for cargo shorts, which are never appropriate for the well-dressed man.

If you decide you must wear shorts, at least opt for a tailored fit, and possibly a mid-length short (one that hits mid-thigh, instead of below the knee), instead of long, baggy cargo shorts. And wear a belt — just because you're wearing shorts doesn't mean you can be sloppy.