There really has been some great literature coming out lately to teach guys what not to do. Undateable is just such a book.

The book, coming out next month, is a collection of 311 things a man can do to be instantly unattractive to a woman. But the blog is something more: an ongoing chronicle of insanely poor decisions men make, rated on a scale from Red Flags (innocent mistakes) to Kiss of Death (you are a freak). This one’s definitely making my Google Reader.

Check it out, and let me know your favorites. This one tops my list so far. [via the Trib]

UPDATE: Of course the minute after I write about how great the blog is, the blog is taken down and replaced by some corporate rubbish advertising the book. (Sigh.)

Although I may occasionally talk about a product that I find interesting, my real concern in this space is overall style. I was thinking about this the other day while attending a fashion show here in Chicago. Many people were wearing things that look good today, but they’ll be embarrassed about tomorrow. In my mind, fashion is transient. Style is enduring, because it involves much more than what you’re wearing.

I think Gore Vidal said it best: “Style is knowing who you are, what you want to say and not giving a damn.”

So if style is much more than the fashion of the day, how can we dress fashionably, but in a more perennial manner (i.e. avoiding fads)? I propose the framework of the three S’s:

Smart Style

Or you could say “sophisticated style”. This means avoiding, for the most part, things that you’d be embarrassed to have your boss see you in. Things that make you look like a child. I admit that I may sometimes dabble in the outlandish accessory department, but overall it’s important to look good while looking like an adult. Remember: the goal is to not be embarrassed when your grandchildren one day see the photos.

Subtle Style

“Subtly is the cornerstone of style.” According to me. This is why, for the most part, you want to avoid high fashion looks. Not only can they make you look unprofessional (see above), but rarely are they subtle.

Also, subtly is about the details. I’ve already mentioned things like your hair and your socks. These are the things that separate you from the guy standing next to you. Use the details, especially when dressing conventionally, to stand out.

Solid Style

I don’t mean solid as in a lack of pattern. I mean solid as in everlasting, stable, reliable. Buy things that are well made and aren’t going to fall apart in a year. Buy things that are going to look good on you for years to come. Buy things you’re not going to come to regret in a year’s time. (I’ve been down that road, and it’s not pretty.)

Within this framework, there is a lot of room for personal expression and experimentation–without the fashion hangover.

What kind of frameworks are you working with? How has your personal style come about?

Photo credit: The ultimate fashion photographer: The Sartorialist

Avid 30 Rock fans will realize that the title of this post is a direct quote from none other than Jack Donaghy. And the man has a point.

Too many times I’ve seen a man impeccably dressed, only to have his hair ruin the entire ensemble. You can’t look like a well-put together gentleman with the hair of a 12-year-old. So here are a few tips to get you started down the road of adulthood hair, Jack Donaghy-style:

Find a Barber

Unfortunately, the barbershop has faded into irrelevance as the men in our culture have begun to seek out cheaper, unisex salons. The problem with these places (as I’m sure we’ve all experienced) is that they have a rotating staff — meaning your hair comes out looking differently every time even if you ask for the same thing.

A good barber will get to know you, and more importantly, he’ll get to know your hair. And he’ll know exactly how you want it each time you walk in the door.

For information on how to choose a barber, check out these guides by GQ and The Art of Manliness. I also found TAofM’s Barbershop Locator to be quite helpful.

Choose a Style

This step is a little more difficult, because what style looks good on you won’t look good on the next guy. So don’t just assume because you see a guy on TV with a haircut you like your barber will be able to make you look the same. A good barber should be able to recommend a hairstyle that looks good on you.

That doesn’t mean that you can’t tell him what you like and what you don’t like. For instance, if you’re a big fan of the show Mad Men (who isn’t?) and want to pull off an old-school style like that, your barber should be able to work with you. In the meantime, this guide should get you started.

And once again, GQ also has an excellent guide to different hairstyles and how to pull them off.

Choose a Product

Different men will swear by different hair products, and rightly so. They don’t come in one-size-fits-all models. It depends on what you’d like your hair to do (see above).

So I’m not going to say to go out and buy any specific type of hair product. But I will say that I’ve been a fan of John Allan’s hair products for years, especially the pomades Blu and Matte.

Spend Some Time

I’m not saying you have to take as long as your significant other doing your hair, but don’t just wake up and go either. Treat the top of your head like it should be treated: as a detail that makes or breaks your look.

This post originally appeared on Smile Like You Mean It. Reposted here for your enjoyment.–cg

Buying a good suit is something akin to purchasing a work of art. You can no more tell a man exactly what kind of suit he should get than you can tell him exactly what he should be hanging from his walls. There are too many styles and genres from which to choose, and every man’s preferences will be different.

However with the right training and a keen sense of style, you can tell good art from the stuff hanging in the Holiday Inn. Similarly you can tell the difference between a man wearing a suit and the suit wearing the man.

First and foremost, it’s a matter of choice. Fabric, cut, lapels, vents – these are all decisions that need to be made. Since suggesting what you should buy depends on a number of factors, from body shape to the occasion, it’s difficult to make specific suggestions as to which suit is right for you. Owning your own shape and your own style will go a long way to figuring out what you can pull off.

So in general, I’m going to go ahead and suggest that, especially if this is your first suit, you should be buying a single-breasted, two-button wool suit with notch lapels and a center vent in the jacket. This should serve you well at most occasions and through most seasons. If you’re a slimmer gentleman you can take a look at a European cut; otherwise stick with the classic American. But no matter what you decide to go with, the most important thing to remember is what I would urge you to keep in mind with your entire wardrobe: fit.

Especially if you’re not familiar with your jacket size, try them on in ever decreasing sizes until you find the one that’s obviously too small for you – then get the next one up. Make sure your shoulders are being hugged, and there are no protruding shoulder pads. You shouldn’t be able to fit more than a fist’s worth of space between your jacket and your body, but should be able to button without straining. Your pants should only have a slight break, and should fit comfortably around the waist.

[Side note : the sales guy is not always your friend. He’s looking to make a sale, not make you look good. Know what you are looking for, and then stick to it.]

Then comes the ever important final step: tailoring. If the place you’re buying your suit from doesn’t have an in-house tailor (or you don’t trust theirs for some reason), take your new purchase to someone reputable. Tell him you want a quarter inch of shirt cuff to show on your sleeves, and if necessary have him alter your pants or take in your jacket. Remember: he’s not a miracle worker, so do everything in your power to get it right out of the store. Under no circumstances should a tailor attempt to reduce shoulder pads or alter a waistline any more than one inch either way.

I hope this simple guide will be a good starting off point for you. If you need any more specific advice for your situation, don’t hesitate to send me an email. I’d love to help you find your work of art.

Photo credit: FromTheNorth

Sometimes things are obvious. Sometimes they’re not. For instance, to me it’s obvious that white athletic socks make any young attractive man look instantly like a grandpa. But for those to whom this is less obvious, let’s state it outright: if you must wear white socks, wear them only to the gym.

While we’re at it, could we also ban gym shoes to the gym? They have that name for a reason.

Socks are like any other accent to your ensemble: they can make or break it. Need some good ideas in this area? Check out this primer to choosing a good pair of socks at the Bonobos blog.

You know that Radiohead poster you’ve had up on your wall since college? It may be time to take it down – especially if you’re considering having dates over. Women may have found that charming back then–or at least pretended they did–but now you’re a full-blown adult with a full-blown adult life. Your walls should reflect as such.

Don’t worry. You can still show Radiohead affection and have a grown-up place. Why not replace it with this print from the Bouf Designer Marketplace? Now your excellent taste in music can be matched by your excellent taste in decorating.

Not a Radiohead fan? I forgive you. Try Louis Armstrong, The Dude, or for some Chicago love, Muddy Waters or Bill Murphy. [via Cool Material]

And if you’re looking for tips on what creepy looks like…

I’ve always wanted one of the functions of this blog to be to give normal guys practical style tips for everyday life. And what could be more practical than buy less.

Specifically, buy fewer jeans. Get one pair that fit well, look good, and go with anything. That’s the advice Scott Schuman gives in the latest British GQ, and I wholeheartedly concur. It took me a few years to catch on to this simple idea. I went through lots of pairs of jeans–but I always had my favorite. It was freeing when I realized I didn’t have to wear the jeans I didn’t like.

Get a pair that work and are meant to last. Give the rest away – maybe they can be someone else’s favorite.