I stick with the Preppie look; one can't go wrong by wearing the same clothes your granddad wore. The secret is to concentrate on classic American looks, natural fibers and materials, top-quality stitching, and lots of woodsy plaids and country-club pinstripes. Silkscreened T-shirts, polyester garments, flared pants, and other trendy swish-of-the moment styles are for teenagers and the Queer Eye patrol. One should always dress appropriately for one's age; nothing's more embarassing than seeing a grown man who ought to know better slouching around in public in kids' clothes.
Buying clothes isn't difficult if one follows a few simple rules.
First rule: you get what you pay for. Although not all expensive clothes are quality clothes, all quality clothing is going to be somewhat more expensive than clothing of lesser quality due to differences in materials and workmanship. Over time, a thifty man will develop a feel for which labels represent a good quality/value balance and which are overpriced junk; the idea is to buy the best clothing available at less-than-retail prices. (A good rule of thumb is “Think Yiddish, Dress British”.) In my own experience, I've found that good-quality clothing can be had from Ralph Lauren (i.e. Polo), L.L. Bean, Réne Lacoste (the “alligator shirt” people -- no longer affiliated with Izod, by the way), Burberry, Brooks Bros.,Harrod's, and the Neiman-Marcus' Men's Shop, among others. These are all reliable sources of classic, masculine apparel.
Rule Two: Shop by internet or mail-order catalog whenever possible. Most stores that carry men's furnishings are located in malls or similar environs and will almost certainly be full of slack-jawed yokels, gum-snapping/hair-tossing teenage girls, guys with their pants around their knees, and clucking mother hens. These nightmarish situations are to be avoided at all costs. If you must buy from a physical store, avoid endlessly preening in front of mirrors or stripping to your skivvies in dubious dressing rooms; instead, know your sizes (write them down!), go straight to what you want, buy the items with a minimum of fuss, and try the garments on at home. If an individual garment doesn't fit, look, or feel right, take or ship it back and exchange it.
Rule Three: Dress Yourself. It is your duty as a man to know which clothes are appropriate for your age, body type, and pattern of activity. Feel free to accept advice from the shopkeeper and/or your wife, but allow no one to decide for you what you will wear; you're a big boy.
Rule Four: Steer Clear of Trendy/Casual Crap. At all costs avoid the “fashion” sections of department stores and trendy joints like Structure, The Gap, Banana Republic, and other mall-type retailers -- all they sell is cheap crap, lo-ryder gang pants, homo-riffic club clothing, and other junk fit only for teenagers and degenerates. One should also avoid “workin’-class” stores like Wal-Mart and other discount chains -- their clothes are almost always shoddy, ill-fitting imported junk meant for the Trailer Park / NASCAR set. (No offense to manufactured-housing residents or stock car racing fans.) If one needs cheap everyday-type clothing, the Army-Navy store is an excellent source of quality goods -- especially for winter clothes, work clothes, and hats. Goodwill and Salvation army thrift stores, yard sales, and rummage sales are also good places to look for good clothing at unbelieveable prices -- a bit of careful shopping can net you great deals, like the pair of London Fog trenchcoats (retail price: $60-$100 each!) my wife found for me at a church jumble sale for $2 apiece.
Rule Five: Remember Your Head and Feet. Want to look like Michael Moore? Wear the same grubby sneakers, wrinkled chinos, rumpled plaid flannel work shirts, mustard/kraut-stained logo t-shirts, and Cubs ballcap as he does and you will. (Forget to shave or shave badly to complete the picture.) Want to look like '60s-era Sean Connery? Wear shoes and hats that are clean and are appropriate for your age and the clothes you're wearing them with. The point? Your top and bottom extremeties need clothing too; all the quality threads in the world won't do one a bit of good if one wears the wrong hat and shoes with them. (Tennis shoes are for the gym; wear leather shoes for everyday use, boots for yardwork, and dress shoes with a suit. Never wear oxfords, brogues or other lace-up dress shoes with white or black tie; patent leather opera pumps are the only correct shoes with a tuxedo.) In short: a real man wears the correct shoes and hat for the occasion. (And never wears a foam hat, a tam o'shanter, or a backwards baseball cap.)
Good clothes and good grooming are a natural part of the life of a gentleman, but there's a world of difference between a well-dressed, well-groomed man and what in German might be called ein parfumetier Schwöller (a “perfumed pansy”). A Real Man wants to dress handsomely and appropriately for his age, station, and activity, but never seeks to be “on display” or otherwise “fabulous”.
Screw metrosexuality, foppishness, and dandyism. The 1955 Highland Park Texas look (i.e. classic Ivy League prep) is handsome and manly and won't look stupid a decade from now. The secret of looking good is not to follow fashion but to stay neat, clean, and buy the best-made, best-fitting, most conservative clothes you can at the lowest price available.
You mean you don't have a magical closet? I have a magical closet. Old clothes vanish into the void, and new clothes appear. Every man should be so lucky.
Rule Five: Remember Your Head and Feet. Want to look like Michael Moore? Wear the same grubby sneakers, wrinkled chinos, rumpled plaid flannel work shirts, mustard/kraut-stained logo t-shirts, and Cubs ballcap as he does and you will. (Forget to shave or shave badly to complete the picture.) Want to look like '60s-era Sean Connery? Wear shoes and hats that are clean and are appropriate for your age and the clothes you're wearing them with. The point? Your top and bottom extremeties need clothing too; all the quality threads in the world won't do one a bit of good if one wears the wrong hat and shoes with them. (Tennis shoes are for the gym; wear leather shoes for everyday use, boots for yardwork, and dress shoes with a suit. Never wear oxfords, brogues or other lace-up dress shoes with white or black tie; patent leather opera pumps are the only correct shoes with a tuxedo.) In short: a real man wears the correct shoes and hat for the occasion. (And never wears a foam hat, a tam o'shanter, or a backwards baseball cap.)
Absolutely. Head and feet are important. Engineer boots should be worn for everyday activities. Steel toe is preferable, but if you're not very active, or ride a moped, soft-toe is ok. White Reeboks are ok at the gym AS LONG as the other guys see you put your boots in the locker. Under no circumstances are pumps acceptable.
I won't be caught dead without a do-rag. Flames for casual BBQ's, solid colors for nights out on the town and leather for formal wear. Occassionaly a skull cap or speed sock can used in lieu of a do-rag, but trendiness comes with a price and RUB's are pansies. The best thing about the do-rag is that the pump wearing pansy knows you're going to beat the **** out of him if he complains.
As soon as we solve your pump problem, I'll help you understand when it's proper to wear a chain belt (At club when you can't carry a gun or a knife), and which hand to hold the belt in, and which hand to hold the knife.
Lol, now watch someone take this too seriously.
One of the greatest benefits of my weight loss program this year is that I can now buy normal looking clothes and not that overpriced and atrocious looking junk from the Big & Tall shops that I was forced to frequent before. When you go from a size 50 waist to a size 36, your options multiply tremendously. I happily threw all my old clothes away during the summer and once I get to my target size (34), I'm buying all good quality stuff. In fact, I'm heading to L.L. Bean online to get some of my fall clothing shortly.
And let me add...Since my lifestyle only demands me getting "decent" once a month or so(Golf, wedings, and funerals), Second hand stores are a valuable resource for obtaining "preppy" type clothes at great prices.
And you're right, the "preppy" look (especially these days)is easy for us "fashion challenged" blue collar types to get right fairly easily. How hard is it to match kahki?
A good place around Atlanta for new, custom tailored suits and business attire is "The Men's Warehouse".