A: To transition seamlessly from chilly New York to tropical Tobago, try a lightweight cashmere sweater over jeans.  It’s a comfortable casual outfit that travels well on a plane.  Add a pashmina for style - and to use as a blanket on the plane.  If you carry a large handbag on the plane, you can toss the pashmina right into the bag upon your arrival in Tobago.

While in Tobago, you’ll want to be ready for temperatures in the 70s and 80s. Here’s what you need to bring:

Tops: Pack some cotton tees and tank tops, as well as one dressier top.

Sweaters: A single cotton sweater will suffice.

Bottoms: Bring one pair of shorts and one pair of cropped pants.  You can also bring a casual skirt, if you’re going to need to dress up.

Dresses: One sundress should be enough for your short trip.

Shoes: One pair of flip flops for the pool and beach, and one pair of shoes that works for dressier occasions.

Accessories: Hats and sunglasses are a must, since sunny Tobago is so close to the equator.  Try to stay out of direct sun for long periods of time; try shady spots under umbrellas and trees.  Don’t forget your sunscreen!

Clockwise, from left: 3/4 Sleeve Zip Anorak, Bustle Back Trench Coat, Dahlia Loose Cropped Sleeve Tailored Jacket, Karen Millen Casual Funnel Neck Lightweight Coat.

Since it’s nearly Spring, it’s hard to find good chilly weather coats in stores.  Here’s four suggestions for coats that bridge the gap between Winter and Spring:

3/4 Sleeve Zip Anorak | $74.99 (sale) at Banana Republic
The light color and collarless neckline allow this anorak to transition between casual and formal.  And I love the look of this crisp white jacket over a printed dress.

Bustle Back Trench Coat | $97.41 at ASOS
I know you don’t want a trench, but would you consider an unconventional take on the classic style?  The ruffled bustle on the back of this coat makes it flirty and feminine–perfect for bridging the gap between Winter and Spring.

Dahlia Loose Cropped Sleeve Tailored Jacket | $115.57 at ASOS
For a more unconventional look, you can try an oversized blazer.  The cropped sleeves on this tailored jacket are singing Spring.

Karen Millen Casual Funnel Neck Lightweight Coat | $328.55 at ASOS
The military style of this crisp cotton coat will elevate your Spring dresses.  It’s not a lighter style - but it will pair well with your cheerful, bright dresses.

A: How lovely—March is the most popular time of year to travel to Japan.  It’s the beginning of their Spring season, which means that their famous cherry blossoms will begin to bloom.

Fashion wise, Japan is a fascinating country.  Fashion forward young people are so creative in dress—influences range from Harajuku (which encompasses a variety of styles, from gothic Lolita to cosplay) to Hime (a new princess craze).  But these edgy styles aside, Japan is a very conservative country when it comes to fashion.  You can get away with casual dress when you’re out seeing the sights, but remember that Japan is a place where attention to appearance is paramount (especially in business situations).  Japanese women have a penchant for meticulously tailored garments—and often wear heels even with casualwear.

For sightseeing in Japan in late March, here’s what you need to bring:

Tops: Bring an assortment of nice, relatively conservative shirts and blouses, both knits and wovens.  Sleeveless styles are OK, but nothing that shows cleavage, nothing tight or clingy.  For late March, long sleeved blouses and knits are going to be your best bet; it may be Spring, but the weather is still going to be a bit chilly. 

Sweaters: Pack a couple of versatile sweaters to layer over your tops; this will allow you to dress in layers to adjust to the heat and cold. 

Bottoms: Your bottoms wardrobe is going to center around long pants.  Pack a couple of pairs of casual pants, and one pair of dressier pants.  You can also bring jeans—tourists do wear jeans; however, they’re somewhat less common amongst the more formal Japanese women.  Skip the shorts, but cropped pants are do-able if they work with your figure. 

Dresses:  If you’re going to be attending any more formal events, you can also pack a dress (knee-length or longer) for the occasion.

Outerwear: For late March, a light jacket should suffice to keep you warm (especially if you’re layering with sweaters).

Shoes:  If you’re planning on bringing only one pair of shoes, you will want a comfortable yet stylish flat that will work for sightseeing and dressier occasions.  I recommend a pair of Cole Haan flats with Nike Air technology or a pair of Softspots with a tempurpedic footbed. 

A: High quality fabrics and structured silhouettes are the key to a more professional and mature look, while extra details add a fun and casual element to a work outfit without taking away sophistication.

Do a different take on the suit jacket: the cropped length and flower pin are a little more casual than your normal business attire, but the silhouette is still put-together and business-casual.

Flower Pin Blazer | $24.80 at Forever 21

Wide Leg pants in basic black, dark grey or a dark pin stripe pattern are a must-have. After all, pants feel more business-like than a skirt. Remember: tight-fitting pants are a dead giveaway to youth, so make sure you choose a cut in a wider leg and a looser fit to keep your attire appropriate for work.

A blouse is an essential for a young female professional – it can be paired with skirts, dress pants or trouser jeans depending on the type of workplace, and it fits nicely under a blazer. If you choose a blouse like this one, the bright coral fabric adds a touch of youth, but the elaborate detailing at the neckline adds an air of sophistication.

Patterns are a great way to add some flair to a work outfit. The knee -length hem and sleeves are all relatively conservative, but the geometric print adds visual interest, so you get the best of both worlds. To add another element of maturity and structure to the silhouette, you could replace the fabric waist tie with a more substantial wide belt.

Patent Pumps are an easy, everyday work outfit complement. Pumps are classic and sophisticated, but the patent leather shine makes for a younger look and will stand out more than your typical leather pumps.

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: 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:

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.