Proper layering is absolutely foundational to a man’s style.  Whether you live in snowy Boston or sunny Miami, whether it’s the peak of summer or the valley of winter, the principles of layering will help you craft the right look for whatever your day brings you.  Presenting our five golden rules for layering:

The dress shirt and tie is one of the most foundation combinations for men, but it doesn’t have to be boring.  Sure, you can mix your solid colored ties with solid colored dress shirts - or even your striped tie with the colored dress shirt - but you needn’t limit yourself to a single print or pattern.  We love the look of mixing and matching patterns with shirts and ties, especially now that mixing and matching different prints in the same outfit is no longer reserved for the fashion forward.

But when you’re mixing and matching different prints, how do you make sure they work together?  The key is to tie the prints together with a motif - be it size, pattern, and/or color.  

Size: If you have two different prints, they’ll work together if the scale of the print is similar.  Two small prints will complement one another, as will two oversized prints.

Pattern: If you have two patterns of the same style, such as two plaids, you’ll do best by mixing up the scale of the print.  A small plaid with a large one, for example, will create visual interest.  Otherwise, the look can come out feeling too matchy-matchy.

Color: Sometimes all you need is a shared color to make two wildly different prints work together.  Color can work its magic to synchronize even multiple prints in an outfit; it’s the motif of choice to leverage when you’re combining three or more patterns in a single look.

A: Just as dark colored clothes are more versatile than their light colored counterparts, shoes are also more versatile when they are dark.  Darker shades of brown, for example, work with many more colors than do lighter shades of brown.  Because of this versatility factor, I’d recommend that your shoe wardrobe include a few good pairs of black and darker brown dress shoes in a variety of styles (captoe, bucks, wingtip, etc.) before expanding to lighter colored shoes.  

Even though light brown shoes aren’t super versatile, you still have a few good options.  As you mentioned, light brown shoes complement navy blue nicely.  And they also work with light sandy colored pants.  Beyond that, you may also want to try dark olive green dress pants with your light brown shoes.  Other than these three options, however, it’s going to be tricky.  I’m not saying light brown shoes and other colors can’t work; I’m just saying I haven’t seen it done that well (at least, not yet).

A: If you’re reading blogs like this one, then you must be dressing much better than a typical government man in a sack suit, in which case, you’ve already won half the from-work-to-a-night-out battle.

First, if you’re going to more…intellectual…events such as museum exhibit openings or galas, feel free to keep wearing the suit.   Chances are most guys will be wearing one, too (well, at least I would hope they would be).

There are also a few quick things you can do to “casualize” your suit.  Go ahead and loosen your tie to add a nice bit of sprezzaturra to your look.  You could always just lose the tie (and belt, perhaps) altogether.

If a full suit is too formal for you, you could try the dark denim and suit jacket look, with or without the tie.  Make sure you tuck in your shirt though.  Warning: this look is rather cliché, but at least you’ll fit in, right?

If you wear a three-piece suit to work, you can lose the jacket altogether, so you’re just sporting a waistcoat over your shirt and tie. Or, replace the jacket with a sleek, leather bomber jacket, with or without your waistcoat.  Black leather jackets make for very sophisticated, urban nightlife wear, and when they’re done right, you look great.  Switching out your trouser pants for jeans (and keeping the waistcoat) will give you a refreshing take on the dark denim look (and one that I favor at the moment).  You may look like you stepped out of a Spurr catalog, but that’s really a good thing.  Keep the tie in all these outfits.

I don’t know what’s happening, but the level of sloppiness in what some guys are wearing is simply getting out of hand.  Loud colors, ill-fitting clothes, sunglasses at night– it’s not stylish, it’s sloppy.

If you want to look as if you don’t care, that’s fine, but please do it with style.

Or more specifically, with sprezzatura, the Italian term for “artful dishevelment” as I call it (it’s not a literal translation).  You may do it already without knowing: sprezzatura is dressing like you don’t care, taking a nonchalant attitude with your appearance—when in fact you do take time and effort to create your look. 

The trick to pulling it off is subtlety, confidence and an otherwise impeccable outfit.  Let’s examine probably the greatest example of sprezzatura, Mr. Gianni Agnelli. Look at this picture of Mr. Agnelli in deep thought.  What is peculiar about his outfit?

Look carefully…do you notice his wrist?  It’s more apparent in this photo because your eye is naturally drawn to that area, but it has to do with his wristwatch.  Mr. Agnelli would often wear his watch outside his shirt cuff but under his jacket. 

The trick to successful artful dishevelment is twofold: subtlety and great sartorial know-how.  Imagine meeting Mr. Agnelli.  Would you even notice the watch?  Only if you looked carefully.  And that’s the point: the fashion quirk is subtle and understated.  If Mr. Agnelli didn’t comb his hair or if he wore an extremely wrinkled dress shirt, the dishevelment would no longer be “artful” but simply sloppy.

But even more important is that Mr. Agnelli’s suit is impeccably well cut.  He has great sartorial knowledge and flawless taste—and it shows.  If he wore an ill-fitting suit and a strange shirt/tie combo, people would consider him sloppily dressed.  But because his suit fits him perfectly, he still looks sharp.  That’s the fine line between artful dishevelement and simple sloppiness.

First of all, notice the loosened tie.  Many men do this out of comfort, but they don’t consider how sloppy it can look.  But when Mr. Bastian does it, it looks stylish. Also, notice his jacket cuff.  See the two buttons unbuttoned?  Finally, look his unbuttoned jacket.  There’s a style “rule” that suit buttons should always be fastened whenever you’re not sitting.  Mr. Bastian looks like he’s giving that rule the proverbial middle finger.  You know he knows that rule, but he doesn’t care.  Sprezzatura is as much about confidence and attitude as anything.

I’ll share one more sprezzatura example: Stefano Tonchi.

Take a look at two things: (1) the single button fastened on the jacket, and (2) the part of the collar outside the jacket lapel, but not in a Tony Montana kind of way.  That’s his subtle quirk; what’s yours?

Notice in all three cases the lack of obnoxious wear: well cut suits with no loud colors, and confidence without cockiness.  That’s what separates these three from the average guy at a club on a Friday night.

It’s hard to look like you don’t care when you do.  When it’s done wrong, you have stereotypical “Los Angeles fashion”; when it’s done right, you have Mr. Agnelli, Mr. Bastian, and Mr. Tonchi.  It’s the difference between sloppily bad and eternally cool. 

Style tip? Steven Alan produces a great line of shirts that come wrinkled (if you’ve never seen a display of his clothes, they even hang on the rack at stores wrinkled and creased).  These shirts are a great place to start if you’re trying to get a feel for this sprezzatura.  But the bottom line is that true sprezzatura can’t be done for you and no one can tell you how to pull it off; it’s about feel.  And it varies from outfit to outfit; a wrinkled shirt in one outfit won’t necessarily look good in a different outfit. 

A: Yes, tweed does seem to be back, but take care in how you wear it.  The tweed jacket can be refreshing and cool, but it needs to be done right.

I think tweed gets a bad rap from old school professors who wear it with patches on the elbows.  It can be worn with style, but I’m a bit more classic than the folks at GQ and Esquire, who seem to be pushing tweed as a trend for Fall.  I tend to think of tweed as “country” wear, where sophisticates sip on cognac and smoke pipe tobacco while wearing a fine tweed jacket.  Maybe that’s just me.

If you want to do tweed in the city at night, you may be able to pull it off with the right fit and complementary clothes.  If I had to make one outfit with a tweed jacket, I would start with a medium to charcoal gray tweed jacket (with a slim silhouette, lapels and no patches, of course).  Under that tweed jacket, wear a sweater or button-down.  And finish the outfit off with a pair of dark denim jeans (navy or black, if you like this Fall’s black jeans trend) or even pinwale cords. 

Whatever you do, keep your outfit simple; you’ll already be attracting attention for wearing tweed.  Let people admire the cut of your jacket—don’t distract them with a complicated pattern.  Oh and contrary to the pictured J Crew example, skip the t-shirt under the tweed blazer look. The wool and the rich tweed texture make this jacket more dressy, and the t-shirt tends to make the look immature, not young. The J Crew guys saved the look by layering the cardigan over the t-shirt.

I don’t know about you, but I’m a spiller.  Sauces, drinks, errant food items.  To keep my clothes clean, I have to be vigilant about stain removal.  For tough stains, I use a stain stick (which fits conveniently in a small handbag).

Especially useful if you want to revive a sweater that’s been sitting in your oversized handbag–or a blouse that’s gotten crumpled.  A steamer is easier on your clothes than an iron is, and it’s even simpler to use.  If you’re sans-steamer (e.g. on vacation), try hanging your clothes in the bathroom and run the shower on the highest heat.  It’s not as effective as a real steamer, but it works in a pinch.

Have a small rip?  A button that falls off?  You don’t need a mini sewing kit (though props to you if you have one).  Simply use a safety pin or two to pin your clothes back together.  I keep safety ins in different colors (black, matte silver, and white) so I can choose the pin that best blends with my clothes.

Did your hem fall down?  You don’t have to bother with pinning it.  Double stick tape will do in a bind.  Just remember to splurge on extra sticky tape–and to get your hem sewn back up afterwards.

What’s your best fashion emergency tip?  Share it with us in the comments!

To find the right sunglasses for you, start with the shape of your face.  Everyone’s face is unique, but there are a few general shapes into which faces can be categorized.  The basic idea is to get a pair of sunglasses that balances out your face shape; that is, a pair that exemplifies the opposite of your face shape.  Moreover, the edges of the glasses should “frame” your face exactly.  If the outer edge of the lens’ frame is wider or narrower than your face, the glasses don’t fit.  Oh, and always make sure you try on the pair in person before buying them.

(2) Often, like with the classic Wayfarer (probably the most timeless pair out there), you can put in regular lenses and wear your sunglasses as a stylish pair of regular glasses.  Go to your optometrist for more information.

A: One time I was at a fancy restaurant in San Francisco.  It was the kind of place where you have to wear a jacket to get in, and if you show up without one, they give you one from their closet.  I sat down and looked at the menu, which was pretty much completely inaccessible to anyone who’s not a Michelin-rated chef.  Rather than try to decipher it, I asked the waiter as casually as I could, “So how is the steak?”

“Oh, it’s terrible,” he replied.

Now, he was being sarcastic, but I got the point: whatever I ordered, it was going to be great.

If you pick the right restaurant, you don’t have to know anything about food and can rest assured that you’ll get a good meal.  Likewise, if you pick the right tailor, you don’t need to know anything about clothes, and you can rest assured that you’ll get a great suit.

Sure, I could give you a long laundry list of things to look out for.  But if you’re going to the right place, I’m certain that the tailor will be doing these things anyways. My one piece of advice would be to know exactly what you want in terms of color, fabric, and style going in.  The best tailors don’t give their input; rather, they simply do what you want them to do.  Besides, the whole point of bespoke is to make a suit for exactly for you.

If you haven’t gone down the bespoke path before, you likely don’t have a good bespoke tailor you can trust.  So do your homework.  Search online for user reviews of tailors in your city.  The bigger the city you live in, the pickier you can be, of course.  When you find a tailor that gets consistently favorable reviews, go visit the tailor and ask to see his/her work.  See if the tailor will let you talk to some of his/her customers and ask them about their experience.

Also, a “huge premium” can actually be really huge when talking about bespoke.  The Kiton “K50,” aptly named because it takes approximately 50 hours to create, costs $30,000 to $50,000, and is made exclusively by Kiton’s chief tailor who personally measures and fits the client.  If you already knew this and still are willing to pay this kind of premium, try Wilkes Bashford in San Francisco, which measures bespoke Kiton, or Kiton in New York.  If you’re in London, check out Kilgour or any other fine tailor on Saville Row. 

Finally, keep in mind that a true bespoke suit isn’t created overnight.  A bespoke suit will take you a few visits to create.  And a good bespoke tailor will allow you to wear the suit, get it cleaned a few times, and then go back for more tailoring for a perfect fit.

Style Tip 1: For more information on the bespoke process, and what you should expect to do (roughly) with each visit, be sure to read this discussion from Ask Andy About Clothes.