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Q. I’m attending a wedding in October in the Berkshires in Lenox, MA. The wedding is in a historic mansion and is at 1 p.m. The bride is encouraging guests to wear fall colors, and said that her friends are wearing cocktail dresses. Cocktail dresses seems a little dressy to me for an afternoon wedding in artsy Lenox. Any suggestions for this 40 year old?

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A. A cocktail dress typically refers to a shorter length dress, which is perfectly appropriate for a 1:00 wedding. And if the bride recommends a cocktail dress in fall colors, then you should do your best to honor her wishes. Here are some great age-appropriate dresses to wear to the wedding that you’ll surely wear again:

Q. I’m going to a HS reunion in an area that is beach casual. It’s a typical dinner and dancing type reunion. I want to look good, but not overdressed.

A. Want to wow everyone at your high school reunion? You can’t go wrong with a flattering, flirty dress or a sexy top worn with slim pants. Here are two looks for inspiration:

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Q. I’m in the process of losing about 50 pounds. I’ve lost about 10 pounds already and my clothes are starting to get loose. I know I’ll need new clothes soon, but what should I buy? I don’t want to spend too much and would like options that can last me a little while. Yet I’d still like to look stylish while losing. I’m a mom (SAHM) in my mid-30s. Help!   

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A. Congratulations on the weight loss and your ongoing commitment! Buying clothes while in the process of losing a significant amount of weight can be a challenge. Luckily, as a stay at home mom, you can get away with a pared down casual wardrobe.

Since you don’t want to invest a lot of money in clothes that may not fit you for very long, your strategy is to choose simple pieces that mix and match so you can get a lot of wearings out of each piece. In other words, you want to be able to get a lot of looks out of just a few basic pieces.

Some things to look for:

  • Tunic tops - these can be very forgiving and will continue to fit fairly well as you lose weight
  • Leggings - when worn with casual dresses and tunic length tops, leggings can look more flattering than you think
  • Jersey dresses and tops
  • Drapey cardigans and belted sweaters
  • Belts - invest in a few belts that can be used to cinch tops and dresses as you lose weight
  • Inexpensive pants with built in stretch - pants tend to be the least forgiving as you lose weight, so you don’t want to spend a lot of money on items you may quickly grow out of. Opt for slim-fitting styles that won’t look as saggy as you lose weight.

Shop for sizes that fit perfectly now, or perhaps even just barely snug, to ensure that they’ll fit as long as possible.


Q. What’s the best suit alternative in this sweltering heat? I can’t bear the idea of wearing a suit in summer, but need to look pulled together and professional on occasion for work. I am more of a pants girl, so I don’t have a lot of dresses or skirts. Thanks!

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A. For women who prefer wearing pants, the key to dressing comfortably in the summer heat for work is to choose lightweight, breathable pieces. We created 3 looks below using skinny summer pants, silk blend slouchy pants and twill trousers. Start by adding a pretty summer blouse which can either be worn by itself or with a belt. Layer a lightweight cardigan or summer blazer over your blouse to change up the look. You can always remove the outer layer when you head outside for lunch or commute to work.

Q. I am going to a Vegas nightclub in a couple of weeks and I want to look HOT but not hoochy, what can a 40-ish woman wear that will still catch my husband’s eye while looking classy?

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A. Take a cue from our favorite 40-something women: the ladies of Sex and the City. In the latest movie, Carrie (Sarah Jessica Parker) wore several dresses from Halston Heritage for a night out on the town. These retro-inspired dresses are sexy and sophisticated, without showing too much skin. Add a pair of dramatic earrings, gold bangles and your sexiest metallic heels and you’re set. Another option is a pretty printed top with slim white jeans and heels. Here are some looks for inspiration:

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