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EdressmeQ. I have an engagement party to attend (my boyfriend’s cousin) on July 29th.  The event is at 6p.m. at a winery/vineyard and I have no idea what to wear.  Any suggestions?   

A. A dress, a dress, a dress—something summery, not overdone.  A pretty sundress will do with strappy heeled sandals.  Engagement parties are not the wedding, so no need to overdo it. Just look pretty and toast the engaged couple.

Print Strapless Dress by Betsey Johnson, $380 at

Q. I’m 15 years younger than my husband.  We both work out and are fit.  His son is getting married - afternoon wedding.  The bride and I are very close.  She said she doesn’t care what I wear to the wedding.  My concern is that I want to look elegant but not draw too much attention to myself from my attire.  The ex-wife is much heavier than I am, and also 20 years older.  I’m struggling finding the appropriate attire.  A beaded suit is not me at all, yet I don’t feel a black little dress is appropriate.  I’m a very outgoing upbeat person — any advice on what I should wear?
-Formal and Fretting 

A. You’re fit and fabulous and there’s no reason to look dowdy or play it safe and be a wallflower.  Weddings are a girl’s chance to dress up, heck, we just don’t get enough opportunities during the week to pull on a gorgeous dress. And don’t worry about drawing attention—all eyes will be on the bride, everyone else is just an afterthought when we all compare what we’re wearing. So look good in a dress and heels.   I scoured the stores and came up with options that are elegant and sophisticated without being daring.  You can stand proud and know that you look good, but are not making a statement.

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J Crew Avery silk short cross-back dress
(available in many colors)
$195 at

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Maggy London Halter Dress with Charmeuse Waist
$160 at


Anne Klein Dress Silk Georgette Dress
$220 at


Anne Klein Dress Charmeuse Waist Dress
$210 at

Q. What in the world do I wear to a company picnic that I’m attending with my husband July 30?  He works for a rather large corporation.  There will be sports and swimming (which I’m not about to do…swimsuit, yuck!)  Here is my major concerns:  I want to look conservative but stylish.  Also, my biggest physical liability is my arms, so nothing sleeveless!  If you can answer this email I would be eternally grateful!  
-Corporate Dressing Coward   

WhattoweartocompanypicnicA. This is meant to be a fun occasion that boosts employee moral and builds company relationships. You’re there to support your husband and simply enjoy the festivities.  You’ll probably see a sea of men wearing shorts and golf shirts while the women will vary from skirts to shorts to sundresses depending on the activities they wish to participate in.  It only reflects well on your husband to look good, but comfortable, be friendly and join in some of the sporty activities. 

Shorts are such a huge trend this season, we just did a segment on “The View” with tips on finding the best style for different body shapes and have a new style recipe, Shorts Story, with plenty more options.  I think shorts with a short-sleeved top or a fitted button down shirt with the sleeves rolled up will allow you the flexibility to join in activities, fit in with the crowd and sit on a blanket without worrying about what you may be exposing. 

Wear stylish espadrilles that give you some height and bring along cute kicks (not your gym sneakers) to slip into for a few of the competitions. And carry a pretty tote or straw bag to hold your essentials for the day like sunscreen and sunglasses. Add in deodorant and a travel pack of baby wipes so you can clean up a bit and appear fresh if the day is really hot.

summer weight Bermuda shorts, $49.50 at; sport shirt, $35 at; Yellow Box Bolton woven leather wedge, $39.95 at; Skechers Sightsee sporty flats, $49.95 at

Q. I’m under 5ft, a size 14/16 and over 50.  What length of skirt do I wear since I now only wear flatish type shoes.  Do I wear a short skirt, knee length or a skirt to my ankles.
-Skirt Concerned 

A. For your age and petite height, avoid long skirts that hit around the ankles, they will only stunt your height and make you appear even shorter. Obviously avoid the mini since you’re not in your 20’s or 30’s. Look for skirts that are not too voluminous that hit just below the knee.  The length will balance your proportions better and just because you’re wearing “flatish” shoes, don’t give up on choosing stylish shoes whether they’re flats or kitten heels.

Here are 3 skirt options we found at in your size:

Mac & Jac Abstract
Watermelon Print Skirt, $72


Jones New York Signature
Knot Print Skirt, $74


Softwear Soft Touch
Print Skirt, $64

Q. When is the season for cropped pants? What is the best way to wear the new summer short trend?
-Shorts Unsure 

V0416340339630 V1 M56577569831226572-1A. The stores are so flooded with cropped pants and shorts this season that it’s difficult to find a good pair of lightweight pants. Cropped pants have become a year round length for pants, but in order to wear them for each season you need to choose appropriate fabrics.  For summer, choose cropped pants in cotton, linen and denim and pair with flats, sandals, wedges and espadrilles.  For winter, choose cropped pants in wool blends and velvet and wear them with your knee-high boots.

As for shorts, inseam lengths matter. Unless you’re under 25, skip any inseam that isn’t 5 inches or longer - nobody needs to see butt cheek when you bend over or bend down!  Obviously, shorts worn with tees and tanks and cute kicks (sneakers) are meant for sporty activities.  If you’re looking for a stylish option, pair your shorts with a cuter top, add long beads and wear with sandals that have some kind of heel. For a “night out” wardrobe or even casual Friday at the office, pair your longer length shorts (they hit just below or at the knee) with a cute top, fitted jacket and sassy wedges or espadrilles to give you height. For a classic look, wear your shorts with a crisp, fitted button down shirt and roll up the sleeves, a belt with a bigger belt buckle and sandals.

BCBG Max Azria Diana Cuffed Shorts (shown here), $108 at

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