A:  For your tour of Italy, you’re going to want a solid pair of shoes that will not only protect your feet but also comfort them from all of the walking you’ll be doing.  But as you know, shoes that are not only comfortable but also attractive are notoriously difficult to find.  Here’s three brands that we recommend checking out:

Sacco Shoes: Known for a combination of comfort and style, Sacco Shoes can be found at their own online store. Sacco Shoes are especially popular amongst New Yorkers–a huge walking town.

Tsubo Shoes: Tsubo combines athletic details and high-tech comfort features with street style for a fresh take on comfort footwear. 

Pr!vo Shoes: Though they’re a division of Clarks, Pr!vo doesn’t sell your typical clunky comfort shoe.  You’ll see athletic detailing and bright colors–or more classic leather styles.  Our personal favorite?  The Pr!vo "Oso" Skimmer (pictured).

Pictured: Pr!vo "Oso" Skimmer | $79.95 at Nordstrom.

A:  Bomber jackets are versatile and can work with almost any look, from casual to chic. Our best advice is to make the jacket the focal point of whatever outfit you create.  To get you started, here’s three looks you can easily recreate with your bomber jacket:

Everyday Casual: The jacket would look fabulous with a dark wash boot cut jean and a little chocolate brown boot. 

Cozy Chic: Wearing the brown bomber jacket with a camel colored sweater dress is perfect for the autumn weather.

Fashion Forward: Pair the jacket with a crisp white blouse and a pair of black cigarette pants.

Pictured: GoldSign Astor Leather Bomber Jacket | $850 at Shopbop.

The "must haves" for Fall are the clothes that are not only on-trend but also figure flattering.  Here’s our Top 5 Most Flattering Trends for Fall:

Sleeved Dresses
Style Tip: These dresses, which are great for covering heavy arms, work best in solid colors or small prints.

High Waisted Trousers
Style Tip: Balance your slouchy high-waisted trousers with a fitted top for a small-over-big silhouette.

Geometric Prints
Style Tip: Wear a single geometric print at a time–and spice up the outfit with something brightly colored that picks up on one of the colors in the print.  Note that you don’t have to go designer to find great looking geometric prints.  We love H&M for designer-inspired prints at cheap chic prices.

Metallics
Style Tip:  We love metallic shoes, which are versatile enough to pair with this season’s brightly colored dresses.  Which metal to choose?  Try pairing warm colors, such as reds, oranges, and yellows, with gold.  Pair cool colors, such as greens, blues, and purples, with silver.

Oversized Collars
Style Tip: To focus attention on your face, make this dramatic detail the focal point of your outfit—and keep the rest of your look simple.

Citizens of Humanity has a corduroy pencil skirt that hits an inch above the knee that would work well with your lace-up boots.  The corduroy skirt and Frye boots complement each other–very casually sexy. 

To complete the look and to create more visual interest, I would add a pair of textured tights. By keeping the color palette of the skirt and tights neutral, the textures would serve as the focal point of your look.  Enjoy your boots!

Lisbon is a coastal town that oscillates between old and new, formal and informal, work and play.  Fashion is guided by the climate, which is hot and humid during the summer and remains relatively temperate even during the fall and winter.  Think creative layering, unstructured dresses, chunky jewelry, and bright colors.

Berlin is a cosmopolitan, distinctly multicultural city whose style reflects its unique demographic mix.  Berlin style is more experimental and has a somewhat "underground" feel.  You’re going to see more one-of-a-kind pieces, dark colors, and severe silhouettes.  Short shorts, tulip skirts, drapey silhouttes, and dramatically oversized shirts are all fair game.

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: 
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.