A: How exotic to being to the "golden triangle" in India for your honeymoon - I’m quite jealous!  The weather should be lovely - March is Springtime there, so it won’t be too hot or too cold.

I suggest packing a small, colorful, flirty wardrobe for your honeymoon. As Indian people dress so colorfully, you will be sharing in the spirit of the country.  Don’t feel as if you need to bring everything - there are so many beautiful clothes to purchase - or have made for you. 

Do keep in mind India’s traditional culture.  As you suggested, conservative dressing is a must, especially in the towns that you will be visiting.  As such, you’ll want to dress appropriately (e.g. knee length or longer skirts, no exposed cleavage, respectful clothing for the holy sites).

Here’s what you need to bring to India:

Pleated Geo Print Dress | $150 at Banana Republic
A few pretty dresses that pack easily are always practical.  They can each be an entire outfit, and they don’t take up too much space.  Look for dresses with conservative necklines and hemlines. 

With your wardrobe buttoned up, let’s talk about shoes. I suggest flats, perhaps in a somewhat edgy style to counter the feminine outfits.  Flats are the easiest to walk in and are so easy to pack.  Avoid open toe shoes or sandals if you mind having dirty feet (the streets can be very dusty).  One last consideration for shoes - select shoes that slip off easily as some sites do not allow you to wear shoes at all.

As you travel around the country, carry a bag that closes securely, as there is a lot of petty theft.  You can bring a little clutch for evenings when you dine out or go dancing.  Lots of pretty, sexy lingerie should round things out for a wonderful honeymoon.

Last thoughts?  Save room in your suitcase for any beautiful silks or pashminas to bring home.

A: Thanks to the "it bag" craze of the last few years, the price of handbags went through the roof.  But despite this rapid price inflation, great bags can still be had for reasonable prices.  As a rule, you get what you pay for; a high quality investment bag is generally going to last longer and wear better than a lower quality (but much more affordable) bag.  But it’s also important to note that price doesn’t always correlate neatly with quality. 

For a work handbag with maximum versatility, you’re going to want to select a good neutral colored leather (black, chocolate brown, cognac, etc) in a classic shape.  Avoid overt logos, candy colors, and overly trendy styles that will quickly date your bag.  Another consideration as you choose your handbag: the scale of the bag should complement your size.  If you’re petite, for example, we’d recommend opting for a smaller sized bag. 

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).

A: We’ve said this before, but the key to winter style on the East Coast is layers, layers, layers.  The weather can be very unpredictable, especially during the winter, so you’ll need to be prepared for anything.  On top of that, you’ll be going between indoors and outdoors throughout the day, so you need to be able to adapt quickly. January in DC will likely have lows below freezing and highs around the 40s.  Here’s how to get a youthful-yet-sophisticated look for Inauguration:

A: I’ll address the “his” part of this question.  The “bad weather shoes” problem is much simpler if you’re not a white collar worker.  Without a doubt, the first pair of bad weather boots I’d recommend are by Quoddy, makers of high quality bad weather shoes.  As you can tell, however, they are for people who experience a few feet of snow in the winter.

Desert boots are another viable option if you live in a place with a less harsh winter.  Clark’s desert boots have always been around, but nowadays you can find stylish desert boots everywhere from J. Crew and the GAP (via Pierre Hardy) to high end retailers like Tom Ford.  The beauty of desert boots is that you can wear them while walking around the city as well; it’s a bit harder to “urbanize” those rugged Quoddy boots.

If you’re a working man, you have it a bit harder.  You have to wear dress shoes to the office, unless you work in a creative industry.  Certainly, you can wear galoshes, but that option is more practical than stylish (even though Esquire endorses it).  If you live in the city, where the streets are a bit more groomed (e.g. less snow on the sidewalks), you can try wearing dress boots, but again, at a formal, conservative type office, I’m not sure that would fly.  If you do decide to wear dress shoes or dress boots, do wear ones with rubber soles.  The snow and slush will wreck havoc on your leather soles.  If you absolutely must wear leather soled dress shoes to the office, do not wear them outside; instead, change into them at the office.

Last words?  Please feel free to beat up your shoes; in fact, I encourage you to wear them in.  A lot.  Tom Ford ran a series of ads a year or so ago in which a man in alligator shoes was walking through the mud.  I love this; “beat up the pretty things,” as they say.  Buy high quality things and wear them out.  This kind of nonchalance is the essence of American style, so embrace it.

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.

A: While I appreciate the idea of dressing up a plain button-down shirt, the expression "you can’t make a silk purse out of a sow’s ear" comes to mind.  A plain cotton button down shirt is a workhouse garment; it’s not really meant for dressing up for going out at night.

For casual wear, however, I recommend emphasizing the sleek simplicity of the shirt by pairing it with a dark rinse jean and a pair of heeled boots.  Layer on a great looking jacket to keep the look long, lean, and simple.  Bonus points for topping off the outfit with a long scarf, like Clemence Poesy (pictured, left).

To make a plain button down shirt a little more dressed up for daytime, here’s a few ideas for standout accessories:
Necklace: Layer on a bold necklace—or two, or three.  Don’t hold back.  The bigger and bolder, the better!
Scarf: It’s amazing how a scarf can turn a simple outfit into one that’s simply stunning.  Give your plain shirt some personality with a patterned scarf.
Belt: To jazz up a plain shirt, take your belt to the extremes.  Either wear a belt that’s wide or one that’s super narrow.  If you go for the narrow option, consider wearing a two or three belts for a very downtown cool look.
Necktie: Do as men do and don a necktie.  Wear it loosely knotted for a casual menswear-as-womenswear look.