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Casual clothing
White shirt
The ever-classic mainstay in every man's wardrobe, the standard white shirt can be an invaluable clothing item in both casual and professional settings; the key is that it's subtle enough to withstand fashion trends.
What you can wear it with: What can't you wear this with? Ideal for both suits and jeans of all colors, the white shirt is truly your closet's most valuable player.
Blue jeans
There probably isn't a Western man alive that does not own at least one pair of blue jeans. From Levi's to Diesel, the original blue jeans can be slightly faded or a dirty denim, and yet they're still so programmed in our society that we continue to buy them, regardless of trends.
What you can wear them with: Versatility is the name of the game here, and rightly so, as blue jeans look good with nearly anything, from a blazer and dress shoes to a T-shirt and sneakers.
Black loafers
Because most people assume these are not the coolest shoes around, black loafers often get a bad rap. Nevertheless, these are a certified male wardrobe staple, if only because of black loafers' true virtue: their simplicity. Free from laces, the loafer is the ultimate in slip-on, slip-off comfort. And because of their minimalism, they will never go out of style.
What you can wear them with: Jeans, suits or anything else you're comfortable in.
White T-shirt
From thin undershirts to standard cotton white Ts, fitted white T-shirts are a wardrobe staple that may never go out of style, mostly because of their year-round versatility.
What you can wear it with: Provided you avoid overly large sizes, you can wear your trusty white T-shirt with jeans or shorts when it's warm, or as an undergarment under sweaters and shirts in the winter.
Blazer/Sports coat:
Every man knows that, like the white shirt, a good solid-color blazer (preferably black) can be used in numerous situations and can often make shabby-looking ensembles respectable. Obviously, the simpler the sports jacket, the more likely its timelessness; fabrics like the recently fashionable corduroy and anything with pinstripes are a high risk for the whim of future trends.
What you can wear it with: Your blazer can be worn at the office with a matching pair of suit pants, or in a bar with a pair of your most reliable blue jeans.
Sunglasses
Not only useful on the beach, every man should have a pair in his car. When looking for something timeless, avoid big, clunky models, and those that wrap around. Oval-shaped sunglasses are your best bet (especially those similar to aviator glasses, but smaller); these have been worn for years and odds are good this fact will not change.
What you can wear them with: Because of their practicality on sunny days, you can wear them with just about anything, summer or winter.
Formal/professional wear
Two-piece suit
Every man should own more than one suit. Of course, owning just one isn't really a bad thing, because if you avoid pinstripes and flashy colors, and stick to darker hues like gray, black or navy, a quality-made two-piece suit can last a long time... provided of course that you take proper care of it. Remember to always dry clean and store it properly.
What you can wear it with: A two-piece suit is a wardrobe staple magnet, as it goes with white shirts, black loafers, belts, and many other items on this list.
Overcoat
Of obvious worth during cold weather, an overcoat can also spruce up your professional image. But sticking with single-breasted styles, subtle colors and popular fabrics like cashmere can net you an overcoat that will last for years.
What you can wear it with: Overcoats can look killer with a matching blazer, though in cold weather they look good on just about anything.
Solid color ties
Solid, dark-colored ties like burgundy, gray or dark blue are a great investment. Flashy colors like yellow and pink are to be avoided, as they tend to come and go with the trends.
What you can wear them with: Your most trusted suit, or any combination of blazer and white shirt.
Accessories
Cufflinks
What makes the difference between successful and unsuccessful men? Attention to detail, of course -- and a great pair of cufflinks can add a lot to your formal appearance. Silver is the way to go here, as they are usually subtler than gold. Avoid cufflinks with slogans on them.
What you can wear them with: A tuxedo or your finest two-piece suit.
Black leather wallet
Considering how important wallets are to guys, you should get one that will never go out of style. Stay away from anything with Velcro or slogans on it. And remember that nothing works better than a simple black leather bi-fold wallet, as this is a great mix of traditional style, minimalism and practicality.
What you can wear it with: Anything, just as long as you don't leave home without it.
Watch
Not having a watch is like not having a right hand. Therefore, you need something that will last. Forget digital watches or those with flashy colors or designs. Round shapes, subtle numbering and colors (think silver, black or gray), and black leather or steel straps are stylish enough to look great, but restrained and traditional enough to buck the trends.
What you can wear it with: Like most daily accessories, your watch should look and feel good with everything you wear.
Cologne/After-shave
For most men, cologne and after-shave application is such a daily routine that a particular scent becomes part of their identity. For something that won't fall out of fashion, stay away from strongly scented colognes. A bottle of Giorgio Armani's "Aqua di Gio", for example, always seems to do the trick.
What you can wear it with: From a bathrobe to a business suit, your cologne should fit you like a glove.
Black belt
You'd be hard-pressed to find a man who does not own a black belt; it's just one of those staples that all men have. Belts are sort of like referees; they're at their best when you don't notice them that much. The key to a classic belt is to avoid anything that disrupts its slight concealment among clothes, meaning anything that jumps out, like large ostentatious buckles or shiny, flashy leather.
What you can wear it with: Jeans, flat-front pants and suits.
Travel-related & Misc.
Luggage
If you're older than 23, backpacks or the old taped-together suitcases inherited from your father are no longer going to cut it. When buying your own set of luggage, you must take into account its practicality, ruggedness and spaciousness, while avoiding patterns, stripes and polka dots like the plague. Also remember that suitcases with wheels are always easier to handle.
What you can wear it with: Pretty much anything.
Sports bag
For the man who likes to stay in shape, a versatile gym bag is a necessity. Making sure your bag is strong and understated in terms of color, style and design is your best bet.
What you can wear it with: If you've chosen well, this should look good with your professional or casual wear.
Umbrella
Every man should own at least one umbrella, if not more, with one always in the trunk of the car. While the umbrella's worth may be more practical than aesthetic, if you want to ensure longevity, you should stick to solid, dark colors and avoid patterns and designs. Also, the shorter, more compact styles might be easier to transport, but for sheer traditional looks, long, sleek models are the way to go.
What you can wear it with: A two-piece suit and an overcoat, but good for any occasion, especially while getting caught in the rain with a date.
Black briefcase
Almost every professional man has needed a briefcase at some point in time, especially if he does a lot of traveling. While today it's fashionable to own a briefcase that resembles a small traveling bag, the boxy, rectangular models are the most traditional, and coincidentally, those that look the least like purses. Sticking with a slim, black, "boxy" briefcase, then, is a safe bet.
What you can wear it with: Any matching combination of blazer, shirt and jeans, or a two-piece suit and overcoat.
staple stylin' man
For most of us, the items listed above are necessary for our day-to-day lives. Following some of these ideas and tips will help cut down on the stress involved with having to replace these items, and hopefully, they'll delay that reality for as long as possible.
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