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Q. I’m so glad your website turned up in my Google search! I took your advice (archive) over the weekend for Date #2 to a football game. Date #3 is dinner at my date’s house. He is cooking and I’ll be bringing the wine and myself. This is a great opportunity to see what he is like - his style, his apartment, etc. It’s time for me to show him my casual, cute, funky side.  What should I wear? I am 31 and I like to dress classically with something funky mixed in - like jewelry or fun shoes. I usually can pick out outfits but with this date, I am nervous and can’t think straight!
-Great Date

A. Since it‘s about being cute and casual, go for items in your wardrobe that you can get comfortable in.  For example, clothes that you can be cozy on the couch while you’re spending hours talking and enjoying wine.  Wear dark jeans and a great camisole and wrap sweater or a great v-neck fitted cashmere sweater with velvet pants and ballet flats.  Perhaps the flats are patent leather or animal print. And don’t wear too many layers since you don’t want to get overheated and give the wrong impression if you need to take something off. And since your signature seems to be the jewelry, wear one of your favorite necklaces or pair of earrings, but nothing too chunky or oversized.  Keep your look pretty and feminine. And bring along a great bottle of wine and perhaps a mini pie or fresh baked cookies for dessert.

Q. Living in New York, I am surrounded by stylish women. I’d like to adopt some of the popular styles, such as jeans tucked into boots and pencil skirts with heels, but I have a, shall we say, ample lower half and I’m not sure I can pull it off. Can pear-shaped girls wear those styles? Any advice on how to make it work?
-Curvy in NYC 

100506 Ashlee 200X400A. There are ways to make those trends look good on a curvy shape. If you’d like to sport jeans tucked into boots, look for a pair of jeans that are slimmer cut towards the ankle. BUT here’s the deal—these jeans are specifically to be worn with boots and a knit top or sweater that covers the hips or gathers around the hips.  Or wear a longer style button down that isn’t boxy in cut and wear it untucked and add a fitted vest.  You want to balance the top half with your bottom half without drawing too much attention to your curvy hips and thighs.  Ashlee Simpson’s look shown here would look great on a curvier girl.

As for the pencil skirt, there are styles that are cut straight rather than fitted.  While a-line skirts are truly best for just about everyone’s shape, particularly curvy girls, if you wish to try out the pencil skirt trend, look for fabrics that hug, slim and smooth your figure.  And don’t hesitate to add a little help underneath!  We’re big fans of Donna Karan’s Body Perfect shapewear pieces and Spanx undergarments since they are thin, comfortable and slim and smooth out all those imperfections.

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Both of these pencil skirt options from newport-news.com offer a figure flattering silhouette with added control properties that smooth and slim your shape. left to right: Fit & flare skirt (also available in plus sizes), $39 and Control pencil skirt, $39

Ashlee Simpson photo via InStyle

Q. I am attending an engagement party for some friends in Philadelphia in two weeks. I just got a great black halter from Black House/White Market that comes up to a collar neck and has that “subtly sexy Victorian” look. Is it appropriate to wear a halter at this time of year (I would wear it with slacks and boots), and if so, what would you recommend wearing over it? The high neck makes it a little tricky.
-Bare Shoulders

A. The simple answer-yes you can wear your halter top to the party, assuming you won’t be spending time outdoors. And bring along a cashmere wrap to keep your shoulders warm if the temps indoors are slightly chilly.

The longer answer is to consider buying a shortened cardigan that you can wear open, or invest in a fitted dressy jacket that you can wear for several years with dresses, skirts, even jeans and to this party.

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left to right: Nanette Lepore Bonnies Cropped Cardigan, $190 at saks.com; Halogen Jacquard Jacket, $128 at nordstrom.com; Juicy Couture Belted Velvet Jacket, $295 at nordstrom.com

Q. I am wearing a tea-length bridesmaid dress in the middle of January.  What type of coat can I wear?  The dress is lower in the back.   
-Cover Confusion    

A. It’s best to look for a dressy jacket that is slightly cropped and doesn’t go below the hips or choose a 3/4 length that is the same length as the dress.

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left to right: Nanette Lepore Turkish Delight Jacket, $415 at saks.com; Elie Tahari Riley Wool/Cashmere Coat, $798 at saks.com; Trina Turk ‘Ellsworth’ Satin Jacket, $498 at nordstrom.com

Q. I need an answer from someone I can trust. I have to attend a gala for the corporation I work at.  On the invitation it calls for cocktail attire. My son, who will escort me, has picked out a full-length black gown.  I am afraid it is too formal for this event.  Would it be tacky for me to be a little over dressed?  I am usually the one in the crowd that is a usually a little under dressed or barely in the appropriate category.  My son says that for once I should go all out and dress to impress, but I am uncomfortable.
-Overdress to Impress

A. First off, you should be comfortable in this dress to impress situation.  While I want you to look good, I also want you to fit into the setting and not stand out and have co-workers and colleagues wonder why you went full-blown.  In this case, a full-length gown would be too much for the occasion.  A gown is appropriate when the invite calls for it, like at a black tie wedding, a gala, a costly fundraiser, etc. It would be lovely for your son to escort you wearing a dress that hits just below the knee or a dressy skirt and top and perhaps a fitted velvet jacket or cardigan with beading or crystals.

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