(2) When you wear a dress over leggings, the rule is that your dress should fall at or above your knee.  If your dress falls below your knee, you run the risk of visually cutting off your legs.  Not very flattering.

(3) The key to wearing leggings in style is to get the big-over-small silhouette.  So when you choose a shirt to pair with your leggings, look for a roomy shirt that’s anything but skintight.  Skintight top + skintight leggings = Minus points for style.

(4) When you look for shoes to pair with your leggings, look for three styles: flats, boots, and pumps.  Other types of shoes tend not to work as well as these three styles.  Our personal favorite is booties with leggings for a rocker chick inspired look.

A: Boston living is particularly extreme.  Outside, the winter weather can be brutally frigid,  and inside, the buildings tend to be highly overheated – so we feel your pain!

How do you keep warm in super cold weather? The key is to keep your core (e.g. your torso) warm.  If your core, head and feet are warm, your body will keep your extremities (arms and legs) warm too.  So—to keep warm in cold weather, you need lots of layers over your core, but you don’t need as many layers over your arms and legs.  This insight helps you stay warm without looking like you

The key to layer your clothes without looking bulky is alternating the length of your sleeves through the layers. Wearing a long sleeved sweater over a long sleeved shirt, with another long sleeved jacket on top, for example, can really bulk you up.  Here’s how to put together a chic layered cold weather outfit:

1.  Start with a solid base: a turtleneck sweater and a pair of jeans.  To give your waist some extra definition, try a belt over the sweater.  This waist definition is key to not looking bulky– especially if you’re wearing underlayers for extra warmth.
2.  Next, add one of my favorite layering elements: a puffer vest (preferably stuffed with down feathers). Down keeps your core very warm, and it gives you more options for your overcoat.
3.  Over the down vest, bundle up in a long wool (or wool cashmere) coat.  The wool coat will give you a more urban look than a more outdoorsy looking down coat—and it traps the heat generated by the down layer. As for warmth, the wool coat without the down layer would generally be less warm than a down coat. But by layering the down vest under the wool coat, you get the best of both worlds: the warmth of down, but the sleeker, more stylish look of wool.
4.  Accessorize for the cold.  180s earmuffs are a part of any stylish woman’s cold weather wardrobe.  Note that the faux fur lined hood on the puffer vest will also act as a hat/wind-blocker, which gives you an additional layer for your ears and head.

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).

by Colleen Geary, fashion stylist and image consultant

A: To understand how to pair shoes with clothes, you first have to look at silhouette.  Shoes should complement the lines and proportions of an outfit, particularly the bottom that you’re wearing.  We’ll start with the basics—regular trouser pants and a knee length skirt—and then we’ll expand out into other options:

Regular Trouser Pants
For regular width trouser pants, the classic choice is a medium height (approximately 2” tall) shoe.  You can wear pumps, loafers, two-tone shoes…and you can also experiment with different toebox styles.  For a sophisticated look, try pointier toed shoes.  But for a more chic, casual look, you can try a round toe.  If you’re not a fan of heels, you can also try a more subdued kitten heel (usually around 1.5” tall).

Knee Length Skirts
The perfect shoe for a knee-length skirt is a heeled shoe.  Most women prefer to wear a medium height heel to visually elongate the leg, but a shorter kitten heel is also a common choice.  Women who are blessed with extra long legs can also get away with flats, but the rest of us should steer clear of them. 

Wide Trouser Pants
To balance out the width of a wide trouser pant, you’ll need to wear a high heel (3” or taller).  The high heel visually (and physically) elongates your leg line, and it gives your bottom half balance.  If you’re blessed with long legs, you can also try a medium height heel.  But for optimal figure flattery, no low heels or flats allowed!

Skinny Pants
Channel Audrey Hepburn when pairing shoes with skinny pants.  What did Audrey wear?  Ballet flats, of course!  When you’re wearing tight pants, you want a shoe that’s not overly sexy.  So steer clear of high heels and shoes with “toe cleavage.”  The ballet flat (or even really short kitten heels) will do the trick.

Short Skirts
Short skirts are best paired with a kitten heel or ballet flat at work.  If you’re wearing a revealing skirt, you don’t want to go overboard with an overly sexy shoe.  That said, the woman in the miniskirt pictured above made the sexy shoe and miniskirt look work.  How did she do it?  She wore tights to cover up her legs (and tone down the miniskirt), and she wore a heeled bootie.  Because they provide more coverage, booties are a less risqué shoe option than an equivalently high heel.

Long Skirts
Because long skirts and wide trouser pants share similar characteristics (length and width), long skirts require the same shoe options as do wide trouser pants.  So the same rules apply: high heels are best, and no flats are allowed.

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.

Simply wrap the scarf around your neck once and then just let the ends drop where they will.  I think this method is appropriate for indoor wear, as it adds color without overwhelming the wearer or the outfit.  Keep in mind though that it does look pretentious to wear a big cashmere scarf wrapped once or twice around the neck when one is inside.
Best For: Long, narrow scarves.

With a square scarf, you can place one pointed side down in front of your neck, and then take the ends and wrap once around your neck ending with a little tie. 
Best For: Small to medium sized square scarves.

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.