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Q. My mother is searching for a dress to wear to my brother’s August 5 outdoor wedding, taking place at 4 PM, at a B&B-type locale outside of Boston.  As I can’t shop with her, I was hoping for some style suggestions that I could share with her.  I’m assuming that it will be hot, but she told me that she does not like sleeveless dresses – I believe she is a little self-conscious, being a size 14-16, so am hoping to find something elegant yet flattering for this special occasion. (Also, she probably will not want to spend over $200, knowing her!). It’s a tall order, but I would appreciate any help you could provide!
-Dress Frustration

A. It’s her son’s wedding and surely your mom is fretting over what to wear that fits her body and looks great since plenty of attention will be given to her.  I’ve found options that all give arm coverage, range from long to knee length and formal to semi-formal with a few color choices as well. They range in price from around $150 to $300.  It’s an important day, so find the dress that looks and fits best, a few extra bucks will be worth it when you see the photos.


Sean Collection Beaded Dress with Jacket
$278 at




Sean Collection Three Piece Ensemble
$318 at



Edressme 1905 5279716-1



Plus Size Gold Lace Cocktail Dress
from Kiyonna
$178 at




JS Boutique Beaded Mesh Dress
$158 at

Q. I have a predominately white skirt with navy trim.  What color shoe is best?  Navy, white, silver?   
-Color Confusion

A. Skip the white.  Choose silver for a festive, sassy look and navy or black if you wish to be more conservative. If it’s a casual skirt, a nude espadrille or nude/light tan kitten heel sandal is a great choice. Also, be sure to avoid anything heavy or chunky with a white skirt.

Q. My daughter is going to a birthday party, cocktail attire.  She has a beautiful navy blue dress, and doesn’t know what color shoes to wear with it.  I suggested silver or cream, she and her friends say white.  What do you think?
-Who’s Right? 

A. I’m proud to say you’re a mom who still has her cool factor.  You suggested the best answer—your daughter should choose silver shoes. It’s a cocktail party and that means her look should be a little fancy.  Silver shoes will rock her look. White is hard to work into a wardrobe and even if she finds a strappy pair, they just don’t look as sophisticated, stylish or dare I say “fashion forward” as metallic.  A fantastic silver pair can be worn with multiple looks from jeans to colors like white, black, pink, etc. I’m sure there are many more parties in her future and silver is far more appealing.

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 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

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