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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; Rebecca Taylor Jeweled Cardigan, $284 + pencil skirt, $190 at; Diane von Furstenberg Besos Cardigan, $172 (sale) at; James Perse V-Neck Long Tunic and Stretch Turtleneck, $79.99 (sale) at

Q. I have just discovered your site and it is now marked as a “Favorite.”  Wow!  I will be attending my best friend’s engagement party in mid-February.  It is an evening party, thrown by a very wealthy family at their home, which only begins my troubles.  The guests will be a mix of old friends and people with whom I would like to network.  I am an attorney, but I would like to wear something fun that makes a good impression.  HELP!  Also, a little help on what the husband should wear… the invite does not indicate a dress code.
- Party Wear Perfection

A. Since the party is for your best friend, you should make a good impression and dress up for the fete.  Even though you hope to network, this is a festive occasion, so you want to avoid anything resembling workwear. Ask your girlfriend what she intends to wear and use that as a guide while shopping at the store or sifting through your closet.  A little black dress or a patterned wrap dress will surely do the trick, or wear a pretty top and skirt. Be sure nothing is too revealing and wear some great heels and knockout jewelry.

Your husband should wear a sports jacket, button down shirt, tie and nice pants.  He can always remove the tie if the guests are dressed more casually.  Have fun!

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

Some sexy shapers:


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

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:


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

Q. Wow!  Great web site.  I was unable to find the answer to my question, so here goes: I am a 48 year old plus size woman and work as a Legal Secretary for a corporate law firm.  The Powers-That-Be have decided to switch our holiday evening party to a luncheon this year at a trendy restaurant in Washington DC.  I am at a loss as to what would be appropriate holiday attire for this event.  I know it is more casual than an evening event, but I am not sure what would be appropriate for a luncheon. We will be at work in the morning, then walking to the restaurant from the office.
-Work Wear Wonder   

A. While the timing may have changed from evening to lunch, there is no reason you shouldn’t wear something more stylish for the occasion - especially since it’s at a trendy restaurant. This calls for a dress. Wearing a dress will help you stand out from the pants and shirt crowd, give you a youthful appearance and allow you the opportunity to break from the “what you wear to work every day” look.  Add some nice hosiery and heels and you’re ready for holiday cheer.  I’ve picked out some great dresses that are age and event appropriate:

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left to right:
Maggy London Faux Wrap Shirtdress, $138 at
Lily Three Quarter Sleeve Surplice Dress, $92 at
Ruched Surplice Dress, $116 at
Poet Sleeved Faux Wrap Dress, $128 at

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