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.

A: It’s hard to go wrong with a suit for any interview, but of course it may be unnecessary given the industry.  Then again, there’s that saying that those who overdress may feel like idiots, but those that underdress are idiots.  Moral of the story?  Wear a (casual) suit.

I really do think that while suits are traditionally a formal look, they can also be made to look very casual.  It’s the little things that matter.  Here’s three ways you can make a suit more casual: no belt, a skinnier tie that’s loosened just a little bit, and no socks.  Oh yeah, cufflinks don’t scream "formal," they scream pretentious—especially for a creative job. Leave them at home.  Skip the contrast collar too; you can wear it when one day you’re on the other side of the interview table.

And suits can still be "edgy" – a suit by Thom Browne takes some real confidence to wear, for example.  I’d be safe (and thifty), though, and avoid the Thom Browne suit, unless you’re going into a really artsy industry (no negative connotation intended).

Sidebar: If you’re trying to get a job on Wall Street, stick to navy or charcoal and a white shirt.  You can’t go wrong with a solid or striped tie, either.  The conservative culture of such firms may cause the interviewer to frown upon anything more.  Besides, you should be more worried about trying to answer questions about WACC and Deferred Tax Liabilities than what you’re wearing.

A: Congratulations!  I applaud you for having the courage to do what you love, and taking the first step towards your dream of working in fashion publishing.  Just as transitioning from a professional environment to an academic one will allow you much more freedom in scheduling your day, it will also give you much more freedom in what you choose to wear.

That said, I’d recommend placing your suits and blouses in a good storage place, as journalism will also require professional clothes until you reach the heights of Anna Wintour or Carine Roitfield, when designers will be begging you to wear their clothes!  Fashion journalism is no exception, though you’ll get to mix things up a bit more.

As you prepare to enter the world of fashion, make sure you have your foundation pieces in place.  These 10 pieces will provide you a foundation from which to grow your wardrobe—and evolve your sense of style.  Since you’re going back to school, I’d add jeans to this foundation wardrobe as well.  In addition to your standard issue dark rinse blue jeans, try a pair of trouser jeans and a pair of grey jeans. 

Moving beyond the foundations, I encourage you to play with silhouettes and color.  Now is the time for experimentation. Layer!  Take what’s in your wardrobe and try to create new and interesting combinations. 

Once you’ve started to exhaust the possibilities with your current wardrobe, make a shopping trip to add pieces that you may not already have.  Things like layered tops, asymmetrical dresses, cute boots, and an oversized, slouchy bag (which should hold your school books nicely).  But don’t be too anxious to fill out your wardrobe too quickly. You’ll start to develop a more critical eye as you study fashion.  And you’ll no doubt be influenced by the designers you study—not to mention your fellow students. 

A: It’s an odd request, but it’s a valid one.  Looking more mature will not only reduce the "how old are you?" questioning, but it’ll also help you to be taken more seriously at work.  We have a few quick tricks to add age to your look:

Balance out your Round Face:  I’m guessing that the youthfulness in your face comes from a round shape; the rounder your face, the younger your look.  To counterbalance the roundness, look for geometric shaped earrings, pointed collars, and more angular clothing.

Wear Structured Clothes:  The more structure in your clothes, the more mature the look.  I’d recommend building your wardrobe around tailored garments and accessories - double breasted coats, belts, blazers, and other fitted items.

Drape Yourself in Jewel Tones:  Bright primary colors are youthful looking, but deeper jewel tones like emerald or turquoise are more refined.  Neutral colors will also add to the maturity of your outfits.

Wear Makeup:  The key here is to wear makeup that’s not too heavy.  Try makeup that’s sophisticated, like a soft smoky eye for evening.

Slip on a Pair of Heels:  Since you’re only 5 feet tall, you’ll also benefit from a couple of inches of extra height.  Height will help you add years to your look, especially if the shoe is in a sophisticated style.