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Q. I have my own engagement party to attend at the end of this month and have no idea what to wear.  The theme is basically an Après Ski Party, but I really cannot wear just a turtleneck or be all bundled up.  I will be switching between inside and outside and it probably will be below freezing.  Any ideas for a cute, somewhat sexy, outfit without looking too much like that Pillsbury doughboy?
-Pretty Not Puffy

A. You want “Ski Bunny” with warmth.  Start with a pair of boots that can translate from sitting by the fire to walking outside in chilly temps. If you have warm feet and good gloves or mittens, you can pop outside for quick moments without sacrificing your look.  And instead of a coat, why not have a down vest that’s not too puffy nearby.  Choose a stylish cashmere sweater, layer a knit or silk camisole underneath and wear a skinny cord pant or a skirt with tights and nubby socks to peek out the top of your knee high boots. Here are some sweater options:

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left to right: BCBG Max Azria Chunky Cardigan, $118.80 (sale); Max Studio Metallic Striped Tunic and Chunky Rib Sweater, $98.99 (sale) + $218; Aqua Cashmere Car Coat Sweater, $178; Alice + Olivia Long Wrap Sweater, $149.99 (sale) - all at bloomingdales.com

Q. My boyfriend and I are celebrating our two year anniversary in March.  I’ve recently come off worker’s comp and I have put on quite a bit of weight.  I’m 5’8“ and I weigh about 160-165 (I used to weight 130).  The restaurant that we’re going to mandates that he wear a jacket.  I’m wondering what I should wear.  I’m a heavy girl now, so I can’t fit into those form-fitting dresses anymore.  I’m trying to lose weight, but I know I’m not going to accomplish anything in a month’s time.  I was thinking a black dress, since black is a slimming color.  However, should I wear a dress or would a skirt and nice top be okay?  Just remember, he has to be in a suit.  Please help me.
- Dressy Date Jitters 

A. Wear a dress. This season’s multitude of empire waist and kimono style dresses look great on curvy figures and are perfect for concealing a few extra pounds.  Just choose a dress that drapes well and will move with your body. And you can always wear a sexy undergarment that will also help smooth and slim your figure if you feel you need a little extra help. 

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left to right: Sweet Pea by Stacy Frati Empire Waist Dress, $98; Maggy London Matte Jersey Dress, $108; BCBG Max Azria Knot Front Jersey Dress, $240; Maggy London Matte Jersey Dress, $118 - all at nordstrom.com

Some sexy shapers:

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left to right: Wolford Lace - Up sheer tights, $68.60 (sale) at figleaves.com;  Spanx All The Way Up High-Waist Pantyhose, $28 at barenecessities.com;  Bali Lace Convertible All-In-One, $41.60 at barenecessities.com

Q. I’m going on a first date to a restaurant that describes its attire requirement as dressy-casual. I understand that means no jeans, but what are other ideas of what I should wear. Since it is a first date, I don’t want to overdo it and I want to be comfortable, but appropriate. Also, I’m in the Midwest, so it’s cold here.
-First Date Stumped 

A. While I understand you don’t want to overdo it, there’s no reason you can’t still dress up a bit.  I believe part of the fun of dating is dressing up and having fun with your wardrobe—it’s not your work clothes and it’s not the clothes you wear with your girlfriends. I’m a big fan of wearing a dress on the first date.  A simple jersey dress with a wrap sweater or trim fitting cardigan sweater, tights and knee-high boots.  It keeps you warm, it’s not overly dressy and you still show you put effort into your attire.  If not a dress, then wear a skirt, tights, knee high boots and a pretty top.  Skip the pants on the first date, you can always wear dark jeans and a cute nubby sweater on a date to a movie.

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left to right: Ya-Ya Swan Sweater, $345 at shopbop.com; Rebecca Taylor Jeweled Cardigan, $284 + pencil skirt, $190 at shopbop.com; Diane von Furstenberg Besos Cardigan, $172 (sale) at shopbop.com; James Perse V-Neck Long Tunic and Stretch Turtleneck, $79.99 (sale) at bloomingdales.com

Q. First of all, you are absolutely my style lifesaver! I check this website constantly, always hoping to find that you’ve updated your column. It’s wonderful and really useful!

I am going to New York in February, and need advice on what to pack. I know it will be cold and that I will be doing a lot of walking, so I specifically need a few suggestions for footwear (I was thinking maybe a tall black leather boot that could be dressed up or down?) and also just general style advice for a Southern girl who prefers not to stand out like a sore thumb when visiting the big city. My hostess in Manhattan is extremely stylish (works in fashion) and I know we’ll be going out quite a bit, so I need some suggestions for outfits and especially shoes that will be warm, comfortable enough to sight-see and shop all day in, and still look great.
-NYC Style 

A. First off, you need a coat that will transition from day to evening, whether you wear jeans or a dress.  A shearling or wool blend coat that hits around the knees and is tailored to your shape should work for the whole trip.  Dark jeans, a fitted jacket in velvet or wool with a belted waist will work with a t-shirt or sweater by day and a jewel toned top at night.  Pack a knit or jersey dress — by day, layer tights and knubby knee highs with knee high boots, and at night pair it with lace tights and patent leather peep toes.

Include a black or brown pencil or a-line skirt and an animal print top that you pair with the skirt and a belt.  Pack a long sweater that you can layer with a thinner knit or long sleeve top and wear with skinny jeans tucked into knee high boots.  Bring along a pair of stylish “sneakers” or as I call them “kicks” that are meant to be worn with pants or jeans, not to the gym. 

Accessories can help any outfit, from a chunky necklace to a thin long chain that can be doubled or tripled around the neck.  Pack an Hermes or “Hermes-like” scarf to wear around your neck with a white button down shirt, dark jeans and great earrings. Don’t forget a wide belt that can be worn high to make an empire waist look, and if you have patent leather you’d be right on trend. As for boots, you may want to pack two pairs: one with a high heel for night and one with a low heel or nearly flat for day.  And consider two colors to also stretch your wardrobe—like a black high heel and a brown low heel. Here are some suggestions for day and night boots that can be worn with multiple outfits:

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left to right: Nine West Elwell, $161.10 (sale) at zappos.com; Aerosoles Rodeo, $89.99 (sale) at aerosoles.com; Aerosoles Minnesota, $89.99 (sale) at aerosoles.com; Nine West Blum, $107.10 (sale) at zappos.com

Q. For years I have been wearing athletic sneakers with jeans whenever I have on a t-shirt.  My husband recently told me that he thinks this looks terrible!  He considers these shirts as ‘nice’ shirts because t-shirts have logos.  I am at a loss as to what type of shoes to wear with jeans and ‘nice’ t-shirts.  I am not a cutesy type girl, so the little ballet shoes, while adorable, are not me.  I also wonder what color to buy.  Is there a color that “goes with everything”?
-Tee Wonder 

A. Trade in your true athletic sneakers and opt for what I call “kicks” or “trainers.”  They’re the kinds of sneakers that you wouldn’t work out in since they don’t have full support, but they’re cool to walk around in and come in a range of stylish colors.  When it comes to kicks, avoid a pair that is white since they’ll resemble the athletic sneaker too closely.  Black also has a hard time being stylish.  Choosing a main color like brown, blue or green paired with another brighter color as trim will go far in your wardrobe. Also, flats can be stylish without being cutesy and are one of our favorite options to wear with nice t-shirts. 

Since you enjoy wearing t-shirts, why not kick it up a notch to polo shirts or tops with any kind of extra detail like ruching, scoop neck, or puffed sleeves in varied colors.  A colorful pique collared shirt will look far more interesting and can go from activities to a casual dinner while a t-shirt alone is limiting.  Here are a few suggestions of shoes and shirts to expand your wardrobe within a comfortable range:

 

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left to right from zappos.com:  Converse Jack Purcell Dance Slip, $45; PUMA Future Cat Low, $100; Converse All Star Slip, $47; dollhouse Praise, $55.95

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left to right from nordstrom.com: Halogen Long Sleeve Pinch Front Tee, $28; Michael Stars Johnny Collar Top, $51; Hard Tail Cap Sleeve Bubble Tee, $60; Juicy Couture Bubble Sleeve Tee, $62

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