Tao of Bachelorhood

(Photo by Stuart Conner)

You’re looking in your closet the day before your big date. You see some old button-down patterned shirts, some polos, an old pair of pleated khakis and about nine t-shirts from concerts you attended in the ’90s. You start to panic. You look at your shoe storage area, which is the space behind the front door, at your Air Jordans and a pair of rain-ruined brown suede sneakers, and you break out in a cold sweat.

Not to fear. There’s still time to pick up a few items that will not only get you through that date, but also have you looking sharp at work, at the sports bar with your buddies, and maybe even at a relative’s wedding. They won’t go out of style next year or even in the foreseeable future.

For this list I’m leaving out the two extremes: a suit and jeans. If you don’t have a suit, you’ll eventually need one, but not for the vast majority of your daily life, unless you’re a lawyer or stockbroker. Plus, with the items below you can fake your way in some situations. Jeans…well, you’ve probably already got jeans. I’m not including sneakers for the same reason, but a pair of nice white ones can give you a more casual option.

Before you grab that credit card and head out, don’t forget to follow my two cardinal rules of clothes shopping:

1. Buy quality. This doesn’t mean you should pay the highest price; it means you should look for items that are well-made. You want your clothes to last.
2. If in doubt, get a second opinion. Enlist someone you know who dresses well to help you with color and fit.

Now to the items that will make up the foundation of your new wardrobe.

1. Sport coat.

The sport coat, sports jacket or blazer is incredibly versatile. You can wear it with a fitted, colored t-shirt and jeans for a casual evening out with friends, with a nice sweater and chinos if you’re meeting up with that Match.com date, or even with dress pants and a tie for a job interview. It can go places a suit jacket can’t.

The most appropriate color for your first sport coat is blue. I recommend a dark blue, which can look dressy when paired with a nice pair of pants, or go well with a pair of jeans. If you’re extra adventurous you might look at a casual corduroy sport coat or something with a herringbone pattern, but a deep, solid blue is classic, with a two-button front. Trendy patterns, designs and fabrics like velvet are for advanced users.

2. Dress shoes.

A pair of nice black dress shoes can also match up with a variety of looks, and the most versatile of the dress shoes is the lace-up Oxford. You’ll want to pick up a pair with a regular toe (not square, and not the elongated pointy look that will be out of date in a year or two) and quality construction.

A good pair of shoes can last you several years if you’re not wearing them every day. When you’re ready for more, a pair in brown can look good with jeans, and a pair of boots can accentuate your party look. Grab a pair of good white sneakers or stylish casual shoes like Sketchers for urban hiking and you’re ready for anything.

Don’t forget to pick up a black leather belt as well—let’s make that 2a.

3. Casual pants.

This is where you’ll normally get advice to buy a pair of khakis. However, I look in my closet and see about seven pairs of casual pants, not a single one of which is a pair of khakis, and can say you’ll be better off with something different. However, paired with the other items on this list even khakis will look better on you than they do on 90 percent of guys.

Look for cotton casual pants such as chinos, or some casual wool pants. Gray, navy, tan, or black are all good color options—try some on and see which color works best, but you probably won’t go wrong with a charcoal gray wool or cotton pant. Just make sure it’s not too dressy if you’re depending on it as the foundation of your wardrobe.

4. White dress shirt.

This probably sounds like the easiest item to pick up, but there are a surprisingly large number of styles and cuts of the basic white dress shirt out there. However, there’s one secret to looking great in a dress shirt: tailoring.

First, look for a shirt made with Oxford cotton. It’s a cloth with a basket-weave or waffle-like look. You don’t want a button-down collar: usually a “straight” collar, pointy with no tabs or buttons, will work fine. As you expand your shirt collection, consider a “spread” collar for wearing with a tie, and a button-down as a hangin’-with-the-guys option.

Dress shirts are sized according to sleeve length and neck circumference, so make sure you get measured before shopping. When you’ve found your shirt, it’s time to have it tailored to fit you. Most shirt manufacturers make their garments like tents around the middle, and the billowy-fabric look went out with pirate shirts. So take it to a seamstress (many stores offer this option) and have the shirt altered to fit properly.

5. Solid tie.

When you need to go dressier, the tie brings it all together, turning your basic sport coat, shirt and pants a little closer to formal. This is where you can add a splash of color to the basic pieces above. A deep red or a complementary shade of blue are the best options for your first neckwear. From there you can go to a diagonal stripe for a traditional business look.

6. Sweater.

Listen, you can’t wear a sport coat all the time. And when you do wear it, you want to have more options to go under it than just a white shirt. A good cotton or cashmere v-neck sweater can add interest and color to this wardrobe. Again, find a color that complements your jacket. A deep red or contrasting blue are my choices.

Try on a few different cuts and colors: some people can rock a red sweater that others can’t, and not all v-necks are created equal. You don’t want to walk out of the store unaware of the man-cleavage that plunging neckline will expose. You might even find that a crew-neck is more “you”: so be it.

When all is said and done, you want to feel comfortable in your clothes, so shop carefully. These six pieces can form the foundation of your everyday wardrobe, and the only thing more important than looking good in them is feeling like you look good in them.

Related Articles:

• Talking Shirt
• Talkin’ Pants
• What’s Up With Those Shoes?

(Photo by kennymatic)

…and you’re not a member of the Norwegian men’s curling team, I will personally come to your house and slap your hand with a ruler.

I’m fighting an awful head cold right now, but I can finally see straight enough to work on some new stuff for you. Coming up…

Apparently there's a drug dealer nearby. (Photo by Hauggen)

Men struggle with fashion. That’s a plain fact you can prove for yourself just by going to a sports bar. But with some simple guidelines we can all dress better and maybe attract a few more women in the process.

I’m not talking about something like 12 mistakes men make when dressing. When women write these things they get caught up in the minutiae that women may understand, but complaints like “too many fabrics” and “length of t-shirt” are a little fine for many of us to really absorb (unless you’re wearing a belly-t-shirt, dude — that’s just wrong).

No, when an average kind of guy writes a piece like this it turns out more like Asylum’s Top 8 Men’s Fashion Mistakes to Avoid, by Brad Adam, who for the most part nails it:

• Worrying too much about what your buddies will think. This is usually an excuse for dressing down rather than dressing up. Just worry about looking good and let your buddies catch up, which they’ll do sometime around the third girl who flirts with you.

• Not spending where it counts. Find some really nice basic pieces, and spend most of your fashion dollars there. You can wear an awesome jacket with a $8 t-shirt and look great, but the reverse is almost never true. I do differ from Brad here: if you don’t wear a watch in the first place, don’t start just for fashion. But if you’re wearing a plastic digital impulse buy from the drug store, then yeah, upgrade.

• Wearing a dark dress shirt with a suit. This is close to cutting it fine, but dark-on-dark is advanced fashion and even some celebrities do it wrong.

• Wearing dirty clothes. You know that “dot” on the pocket that you can “barely see”? Everyone sees it, they’re just too polite to mention it. And Brad didn’t mention the smell factor: even a clean-looking shirt shouldn’t be worn in public if you had to run 10 blocks to the bus last time you wore it.

• Wearing clothes that are too large. At best, you’ll look 20 years out of date. At worst, your friends will ask when you’re due.

• Mistaking expensive clothes for good-looking clothes. I’ll add that the Ed Hardy t-shirt era ended when Jon Gosselin started showing up in tabloids wearing them. Instead, find something cool at BustedTees, or better yet, a nice-fitting solid colored t-shirt and save yourself money and your friends nausea.

• Trying to be too fashion-forward. You know what the new thing is? Skirts for men. That ought to keep you from straying far.

• Not dressing to the occasion. Again, find a look that works for you, but also remember to adapt to the situation. Jeans to a funeral are always wrong, even if they’re black jeans.

The list could go farther, including “Being a mortal enemy of the ironing board” and “Wearing anything with ‘TapouT’ or ‘Affliction’ written on it” but we’ll let it rest there for now. Now I have to go purge my memory of Jon Gosselin again. With hard liquor.

Top 8 Men’s Fashion Mistakes to Avoid [Asylum]

I’m not someone who watches American Idol until they get to about the Top 5, and even then only if there’s someone interesting, but this was awesome:

I know, I know, I’ve talked about this before, but the General makes a point: after the age of about 16, droopy drawers are an indication that you haven’t mentally aged past 16.

And let me include another link to some great pants: Bonobos makes some well-tailored drawers (although their “signature” slash pocket linings may need a re-think) at a decent price. Their self described “mission to banish the saggy bottom” is a noble quest.

And don’t worry about those saggy jeans: they’ll still come in handy.

With one week until Christmas, you may be sweating the eventual trip to the jam-packed mall to do battle with the masses over the ugly sweaters and iPod knockoffs that remain. I have done this, and found myself waiting in enormous lines to buy pitiful crap that the recipient must then pretend he likes.

Don’t do it.

Let me give you a few options for your buddy, your boyfriend or yourself. Options that are recommended by those who own them, with attractively low prices. The best part is, via Amazon.com you can order these up with two-day or overnight shipping.

Iron Gym Total Upper Body Workout Bar

I just ordered one of these for myself — the recommendations are awesome. This device fits in most doorways (and doesn’t require bolts or screws) and enables you to do pull-ups whenever you feel like it. You can also use it on the floor to make push-ups easier, and even to hold your feet for sit-ups. The Iron Gym folks also say it lets you do dips, but the range of motion for those dips is so limited you’d be better off using a sturdy bench.

But for pull-ups most Amazon users swear by it.

With this you’ll be able to do virtually the entire no-weights workout at home, giving you a workout option anytime you have a spare 20 minutes.

Kenneth Cole Reaction Men’s Wool Pea Coat

If you’re going to buy him an article of clothing, you can’t go wrong with a basic pea coat. They’re great for any occasion that isn’t formal, they work with button-downs, t-shirts or sweaters, jeans or slacks, and best of all they keep you warm.

The Kenneth Cole name won’t do you wrong here. It’s 80% wool, which means it’s warm, and it comes in black or charcoal. Just remember that pea coats tend to run a bit large in size, because they’re meant to be overcoats. They also require dry cleaning, but as long as you don’t spill on it or perspire heavily without a shirt on under it, you should only really need to have it cleaned once a year, before you put it away for the warmer months.

You’ll feel like the guy from the Old Spice commercials — except you’ll smell better (as long as you stay off the Old Spice).

Garmin nüvi 260W 4.3-Inch Widescreen Portable GPS Navigator

Personally I don’t use a GPS — any directions I need I get with my iPhone and Google Maps. But most of my friends love their GPSes, so who am I to stand in the way of that?

This Garmin is the most popular GPS at Amazon (here’s the whole list), and after 493 reviews has an incredible four-and-a-half-star rating. What about the features? Glad you asked. It has a 4.3-inch screen with 2D and 3D map modes, turn-by-turn voice guidance that reads street names, a rechargeable battery, and a touchscreen with a JPEG picture viewer, world travel clock, currency and measurement converter, calculator and more. You can use it in the car or on foot. It comes preloaded with North American maps, and more features are optional via an SD card slot.

If you or someone you know is directionally challenged, stop driving in circles or pulling off at every other gas station. This small investment can pay off in saved time alone.

A word to the wise though: don’t leave a GPS (or even the suction-cup mount) visible in your unattended car. Thieves love them as much as my friends do.

Rules of the Game

Neil Strauss’ original book about his experiences as a pickup artist, The Game, is an all-time bestseller on Amazon. For that reason you may not want to give that book as a gift: chances are your friend/boyfriend/husband has already read it.

Instead, if the guy you’re giving the book to is unattached, get him the sequel by Strauss, Rules of the Game. Where The Game was a story about “Style’s” experiences, Rules is a handbook for meeting women and convincing them to go out with you. It includes word-for-word routines and steps you through the whole process, from openers to getting her home.

Keep in mind that Strauss “works” mostly in the world of nightclubs, which requires a different touch than, say, a supermarket or art gallery. You won’t want to breathlessly recite the “two girls fighting” opener to a girl you see at the bookstore, and not every guy is cut out to dress up like a rock star (for example, I give you Jon Gosselin). However, there are some useful tips you can use in your daily life, and the book is full of stories from Strauss’ life among the party culture of LA.

However, if the guy you’re buying for does happen to have a wife or girlfriend, a better choice might be The Book of Basketball. Bill Simmons is such a good writer he almost makes me care about basketball, plus every minute I spend reading him is a minute I’m not reading Rick Reilly or Mitch Albom. Or if he’s not into sports, get him something by Chuck Klosterman — dude is funny.

I hope this has helped. If so, now you’re golden until his birthday. No, a beer bong is not appropriate then, either.

Dude with woman and cup of coffee, not drawing attention to his package. Unfortunately, not representative.

Underwear is important. If you’ve read my guide to all things boxer and brief but you’re looking for a wider selection, you might want to try the Men’s Underwear Blog. From jockstraps to long johns, MUB keeps tabs on the manufacturers, styles and stores who offer a dizzying array of cuts, colors and patterns.

Word of warning: there’s a slight overtone of guys who like to look at other guys, if you know what I mean (not that there’s anything wrong with that, as Jerry Seinfeld would say). And even if there wasn’t, there’s only so much browsing I can do before burning out on looking at guys in nothing but their skivvies. but I think that even for straight guys like you and me, if you want the lowdown on, say, Xmas-patterned shorts from AussieBum, or eagle-themed trunks from Ginch Gonch (“gonch” being Western Canadian for “underwear”), they’re ever vigilant for these vital advances. And they link directly to the stores so you can buy safely.

Pop on over if you’re curious – but perhaps not from work. Remember how everyone talked when that manager down the hall brought in an International Male catalog…?

[Men's Underwear Blog]

See also:

• Tighty Whities: A Cautionary Tale
• For God’s Sake, Man, Buy Your Own Underwear

You will never look as good in y-fronts as she does.

A new survey by British department store Debenhams says men don’t like buying underwear. And while I think surveys like this are self-promotional junk, there are a couple of points to be made.

First, the survey notes that men under 26 say they prefer “tight briefs,” men 26-33 say they prefer boxers, and men over 33 like “y-front undies.” Since I’ve always understood that briefs and “y-fronts” both mean what we call “tighty-whiteys,” the gist is that guys grow up and gain some sense at about 26, then lose it again after age 33. This jibes with what I hear (not that I talk underwear with a lot of folks — imagine that ad with Charlie Sheen telling Michael Jordan “I’m wearing your underwear” for why).

Maybe I can help you gain some sense earlier: I’ve already gone over the styles you should wear if you remotely think anyone might see your underpants.

Second is this puzzling quote:

“If [a man] buys more than 31 pairs every year, he’s either still trying desperately to impress the woman in his life – or else she’s not The One.”

Who buys 31 pairs of underwear a year (other than Howie Mandel), even when they’re seeing someone? Now that all transactions are computerized, a department store should have average purchase figures, but somehow I don’t think they bothered to use them here.

Also, according to Debenhams most guys are happy to let their mom buy their underpants until their second year of college, and as soon as they get married they pawn off the duty to their wives. I’ve got to say, that seems slightly Oedipal, but it’s probably that the women in guys’ lives notice holes before most guys do.

Just buy enough decent underpants that you have a week or two worth of clean, stylish drawers in your drawer, and replace them when they wear out. No personal assistant required, but a little taste is.

Average man buys his own underwear for just 17 years of his life – and only if he’s got a hot date [NY Daily News]