A:  During the day, you can wear a black and white striped tank under your black dress to make it school appropriate.  Bonus points for wearing thin stripes.  To accessorize, add textured black tights and booties for shoes–perhaps in an eggplant color.  To make the look even cuter, add a brightly colored bag, such as this bright blue bag from Lulu.  Flashes of color with the shoes and bag will make your black dress fun and playful.

For evening, pair the black scoopneck sweater dress with a deep red camisole, black hose and a sexy stiletto or boot.  To add texture and shine, finish off the look with a black snakeskin clutch.

The black sweaterdress, like its cousin the Little Black Dress, has so much versatility–so be sure to have fun with it!

Pictured: Trumpet Sleeve Sweater Dress | $98 at Banana Republic.

You can wear the brown plaid skirt in a way that reflects these preferences.  Instead of pairing the brown plaid skirt with a frilly, feminine white top, pair it with a super casual (and comfortable) top–a tank top or a t-shirt.  As for colors, brown goes well with light and bright colors–such as turquoise, orange, and shades of white.  Finish off the t-shirt and skirt look with equally casual shoes–flats, sandals, or even sport sneakers.

Or, if that look is too casual, try a structured shirt with masculine influences, such as oversized pockets, epaulets, snaps, or D-rings. 

A: 
Black on black makes quite a statement. You can create (at least) three different looks with this style. For a look that’s…

1. Jazzy and zoot suit inspired, try Thomas Pink’s spotted knit tie.

Spot Knitted Men’s Tie | $49 at Thomas Pink

2. Sophisticated and urban, try Thomas Pink’s art deco inspired tie.

Wild Fern Printed Silk Men’s Tie | $49 at Thomas Pink

3. Artsy and unconventional, try TieLab’s Poppies tie. Dramatically graphic.

Pictured: Poppies Tie | $30+ at TieLab

A: 
Rain boots should be fun and whimsical - cheery for a rainy day! My favorites are Kate Spade rain boots. She has an adorable pair called Riley in green with one white bug on each boot, which makes them fun but not overdone.

Pictured: Kate Spade Riley Rain Boots | $128.95 at Zappos

If you live in a place where you need a selection of rainboots, add to your boot collection with a pair of classic Wellington boots. Wellies are not only classic but also chic. Choose a pair in a bright color, such as yellow, to spruce up your rainy day outfits.

Hunter "Original" Boot | $98 at Nordstrom

A:  To transition a summer floral dress into fall, I would recommend going for a "foho" look - folkloric and bohemian. Try pairing your blue flowery dress with:
(1) A cream colored cardigan with embroidered flowers on it to echo the flowers on the dress,
(2) Textured tights, perhaps in a blue which blends with the blue in the dress, and
(3) Fun little ankle boots. 

As far as wearing a summer dress in the winter, I wouldn’t do it - unless you live in a part of the country with mild weather. On the West coast, you could probably get away with layering the dress over pants and a long-sleeved shirt–and then topping it off with a cardigan or jacket. But on the East coast, it would just look wrong.  If you’re a East Coast gal, enjoy the  fabrics and colors each season has to offer, and be happy to pull out your loved dress next Spring!

A:  Since you’re tall and skinny, skinny jeans look great on you, however you wear them.  But we think that an ultra-voluminous top would overwhelm your figure (which can work, depending on the look you’re going for). 

How to wear the skinny jean?  Like Kate Moss, the Queen of the Skinny Jean.  Wear a camisole then add a vest.  The fitted look of the vest-over-camisole plays with the idea of menswear as womenswear.   Another option is to wear the skinny jeans with a very fitted blazer.  Bonus points for a blazer with a three-quarter sleeve.  To balance the sharp angles of the blazer and the jeans, wrap a soft, billowy scarf around your neck. Finish off the outfit with a black ballet flat, sexy black boot, or even calf-high minnetonkas, and people may just mistake you for Kate.

But what if you’re not tall?  Look no further for advice about How to Wear Skinny Jeans if You’re Short.

You can also try going preppy with the white blazer. Pair it with a colorful polo and shorts.  Or replace the polo with a striped or plaid shirt for even more visual interest.  You can get away with knee-length shorts in white or colored fabrics–or even seersucker.  Finish off the outfit with a pair of boat shoes or docksiders.  Very WASP.

More generally, you can wear blazers with almost any type of pants, if you’re daring.  It’s less about what you wear than how you wear it.  While most men keep to jeans or trouser pants in the same fabric for their blazers, you can expand your options to trouser pants in different patterns and textures (very sophisticated when done right), cargo pants, and even shorts. 

Should you be looking with shoes with a slight heel, though, Taryn Rose has a few styles to check out:

Taryn Rose Orbit Pump | $241.90 (sale) at Nordstrom (Pictured)

Taryn Rose Gaby Slide | $435 at Nordstrom

Taryn Rose Adore Wedge | $445 at Zappos

Taryn Rose Darcelle Wedge | $515 at Zappos

A:  The first thing you will need are comfortable yet stylish walking shoes, as you’ll be walking across cobblestone streets.  For uneven surfaces like these, flats are going to be your best bet.  I recommend shoes from French Sole, as they have a wonderful selection of these easy-to-wear flats. 

In Paris, the style was tailored and classic.  Everyone was well groomed and well accessorized–scarves are key. Handbags, eyeglasses, shoes and boots were stylish and edgy.  Think of classic shapes with interesting details–an oversized buckle, an unusually placed zipper. 

As a student, you would need a foundation of tailored jeans, comfortable tees and a few pretty sweaters–choose grey or navy for versatility.  Upon this foundation, add one-of-a-kind type pieces that will give your look personality.  A dramatic tulip skirt, a jacket with an oversized bow, a distinctive chapeau.  I would also pack a figure flattering basic little black dress (LBD), which you can dress up or down with a sexy stiletto. 

As for stores to visit, don’t miss Colette in the first arrondissement–very fashion forward and fun.  Also check out Annick Goutal perfume shops, which are beautiful little jewel boxes.  Galeries Lafayette should not be missed at Christmas–the lights at that store are spectacular.

Christmastime is tastefully beautiful in Paris, and as a bonus, the weather is rather temperate. A good wool jacket or coat in a slim silhouette with a beautiful scarf will keep you happy and stylish while ice skating at the Tour Eiffel.  Bonne chance!

A: 
When you’re wearing a knit dress, wearing the right undergarments is absolutely essential.  Spanx makes wonderful body shapers in a nude color–great because they’re not visible and they hide unseemly lines.

As for designers who make great knit dresses, try Abaete, James Perse, and C+C California.  Abaete knits are lined to prevent sheerness, and James Perse and C+C California knits are made of buttery soft and heavy cotton.  Not only do they drape beautifully, but they’re also not sheer. 

A discussion of knit dresses would not be complete without a note about fit.  Clothes should skim the body and not be so tight that undergarments are bulging. Proper fit and proper undergarments are the "foundation" to looking great in any dress!