A:  These are certainly sexy motorcycle boots!  With standout boots like these, you want to keep the rest of your look relatively simple.  Pair your boots with items that aren’t blatantly sexy–with provocative items, less is more.  Three outfit ideas for you:

(1) Classic Cool: A slim jean in a dark wash and a black turtleneck would complement the boots’ edginess without competing with it.
(2) Menswear Inspired: Wear a crisp, fitted white button down shirt, slim jeans, and a cropped, fitted black blazer. Bonus points for a skinny tie.
(3) Technicolor: Use color as a secondary focal point with a brightly colored overcoat or handbag.  Round out the rest of the look with layered sweaters and a pair of ultra-cool grey jeans.

Pictured: Carlos by Carlos Santana Women’s Pistol Boot | $149.99 at Shoes.com.

A gentleman’s watch should be subtle and classy, not pretentious and grotesque. It can have diamonds and jewels, but only in tasteful quantities. And if it is expensive, it should be not because the 4 karat, D-colors on the face of the watch manage to spell your name, but rather because of the craftsmanship and its timelessness.

What watch to buy? We present to you five watches worth investing in. These watches all have leather bands, the more formal band material of choice, and they look great any time you want to appear sophisticated and refined. Treat them as investments.

A:  There are no hard and fast rules for layering necklines.  However, we have two guidelines that will help sort out the eyecatching combinations from the ones that are just so-so.

Guideline 1: Layer Necklines of Contrasting Shapes
Try a deep-v wrap neckline, for example, over a scoopneck top or a camisole.  Contrasting shapes create visual interest for the eye and, as such, more sophisticated combinations.

Guideline 2: Find Pleasing Proportions Through Your Balance Point
The distance between necklines should be in a pleasing proportion to your own body type.  One technique that helps you discover this pleasing proportion has to do with finding your balance point. 

If you measure your face from the top of your forehead to your chin and then drop down the same distance to your chest area, you’ve found your balance point.  This balance point is the most flattering spot for a necklace or blouse to hit.  From Stonehenge to the architecture of ancient Greece to the art of the Renaissance, there appears to be a cognitive preference towards the Golden Ratio (1:1.618).  Try the Golden Ratio to find the most flattering spot for the second neckline. 

Here’s an example: If the distance from the top of your forehead to your chin is 9 inches, your first balance point (and the mot flattering spot for your first neckline) is going to be 9 inches down from your chin.  The most flattering spot for your second neckline is going to be approximately 14.5 inches (calculation: 9 in x 1.618) down from your chin. 

Pictured: Laila Azhar Standing Cowl Neck Dress + Diane von Furstenberg Caridad Top | $385 and $225, respectively, at Shopbop.

We asked: Are Gloves In or Out?

Style tip?  You can play it safe with neutral colored gloves in white, black, or grey.  But gloves are a great way to experiment with color.  Go on, be daring–and try purple, orange, or green!

A:  The best fashion makes a woman look alluringly stylish, while projecting an image of good self-esteem.  In our humble opinion, wearing skirts that are too short or tops that are too low cut can detract from dignity of the person who wears them.

Flatter your curves with well cut clothes that accentuate your figure without being overt.  Don’t waste money on filler items to build an outfit around clothes that make you uncomfortable. Depending on your age and your body type, a few inches above the knee is usually the most attractive length for a short skirt. Longer pencil skirts can be very flattering and quite sexy as well.

Tights will not hide the fact that the skirt is too short–so say goodbye to the teal skirt and update your look with a skirt that is flattering for your body type - you will look great and feel great!

A percentage of the event’s proceeds will go to Baby Buggy, a non-profit organization dedicated to providing New York City’s families in need with essential equipment, clothing, and products for their infants and young children. 

Lucky Shops
Metropolitan Pavilion
125 West 18th Street (between 6th and 7th Avenues)
New York City
Friday, October 26, 12 pm - 7 pm
Saturday, October 27, 10 am - 7 pm

You can make your blazer less “country club” by changing the buttons from gold to a dark navy blue (if they aren’t already).  Changing buttons is a fairly simple task for a tailor and shouldn’t be too pricey. 
   
As for what to wear with your blue blazer, you can’t go wrong with jeans, as long as they aren’t too similar in color.  You can wear blue, of course, but you can experiment with other colors, such as a darker gray denim.  For more formal occasions, you can still look young in gray pants, such as chinos or flannel trousers. Earthy tones such as brown or olive also work here.  Avoid khakis, which will give your blue blazer an older feel.  As for fit, look for pants that are well fitted and slimmer rather than baggier.

For shirts, a crisp white oxford works well here (when doesn’t it work well?).  You can make the blue blazer more casual by wearing a graphic tee.  For something different, though, try a windowpane plaid or smaller gingham shirt, but don’t get too crazy here.  For those blazers that are dark and inky (the ones I like), a skinny-but-not-too-skinny tie looks great here especially in a dark purpleish/gray. 

Complete the look with brown shoes, a brown belt and even a crisp white pocket square.  You could even get away with wearing white sneakers, but be careful – if they’re too athletic-looking you might give off the Jerry Seinfeld vibe. What to wear?  You can’t go wrong with lowtop Jack Purcells. 

A: 
Even though your dress code may be casual, it’s best practice to dress professionally by choosing a boot that complements your business casual attire.  Rain boots, though functional, often have a playful feel, so it’s your challenge to find one that is not frivolous looking.  Rule of thumb?  When wearing rain boots to work, choose a boot in a classic style. 

We recommend:

Hunter Original Sparkle Boot | $113.95 at Zappos
Love the classic buckle detailing.

Marc by Marc Jacobs Casual Rain Boots | $193.95 at Zappos
You don’t have to sacrifice style when the weather gets wet with these chic drawstring-tie boots.

(Pictured) Aquatalia by Marvin K. Wasabi Boot | $238.95 at Zappos
Patent leather kicks the style quotient of these rain boots up three notches.  We know they’re expensive, but they would look sophisticated paired with a trench coat at work or with a cute jacket and jeans on the weekends - a worthwhile investment.

Style Note: If you happen to work in a more conservative office (e.g. law firm), skip on the rain boots at work and bring an extra pair of dressy shoes with you in your bag.