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Q. My boss wears chunky winter shoes (recently a pair of black Mary Janes with a wide heel) with bare feet. I think this looks incredibly tacky, not to mention being ridiculous because it is cold outside.  She claims it is ok because we live in Florida, and thinks the only reason I find it unacceptable is because I am from a “cold state.”
-Shoe Style 

A. It’s not our intention to outright criticize your boss, but stylewise, we’re not fans of chunky wide heel shoes unless they’re a wedge or platform style with a thicker heel.  Most chunky shoes with wide heels are meant for the younger teen set.  Slimmer, sleeker looks, from flats to kitten heels to pumps, are far more appropriate for the adult set.  There are many comfortable round toe pumps and even Mary Janes that could be pulled off with a bare foot and look more stylish.  As for the bare feet, we girls like to go as long as possible with a bare leg before we have to pull on tights or hosiery.  I have a feeling that with a more stylish shoe, her bare legs may look better to you. Many people in Florida are used to having bare legs all year long so it may take some getting used to on your part.

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left to right: Dolce Vita 6020-4, $125 at zappos.com; Aerosoles Transpose, $84 at zappos.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.

Q. Is it ok to wear high heel boots with cute capri pants in the fall?
-Viva la Capri?

Picture 3-3A. Yes, you can wear capris, just be sure that your capris don’t look summery.  We like to call them cropped pants in the Fall and they should be of heavier fabrics like corduroy, denim or wool. And your cropped pants should cover over the top of your boots, if not then wear fun tights or have nubby socks that peek out just above the your boots.

Theory Calvan C Velvet Pants, $245 at saks.com

Q. I’m hoping you can help me! My cousin is getting married on November 5, 2006 at 4pm on Perdido Beach, Florida. What is appropriate to wear? Nothing has been said re: dress formality. While it’s the Fall season, it’s still the beach and should be warm and I’m unsure of the appropriate clothes and shoes to wear!
-Beach Be-Wonder

A. Since it’s on the beach, my first choice would be a dress that is cocktail length skimming just below your knees, second choice would be a skirt and top. Don’t wear pants—boring for a wedding and you want to move freely on the beach. Choose a light fabric like cotton or silk jersey, but skip linen since the season for that is over. Look for a dress that perhaps has short or 3/4 sleeves or wear one that is strapless, sleeveless or has spaghetti straps and bring along a little fitted cardigan or wrap. Since it’s a late afternoon into evening affair, feel free to wear pretty prints. And be sure to wear flats or low-heeled sandals and assume you’ll be taking them off in the sand so be sure to have nice painted toenails.

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from left to right: Nicole Miller Tiki Print Dress, $310 at bloomingdales.com; Single Wrap Dress, $268 at bloomingdales.com; Lumiani Quarto, $89.95 at zappos.com; J. Reneé Pixie, $78.95 at zappos.com

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