I have a high school reunion to attend and am very confused on what to wear. The invitation stated "business dressy". I was just at another social event with the same attire description and was very disappointed at the array of clothing I saw. Some women were in evening gowns, others in slacks and sweaters, and some, myself included, were in blouses and skirts. Some women were clearly so confused they wore the flashiest outfit they could find! I actually felt under dressed. My instinct is to wear the evening/ cocktail gown because I would rather be over-dressed than under-dressed. However, I don't like not following the rules, just in case everyone else does. Do you have a recommendation on what I could wear that would be dressy enough without being out of place and not make me feel under-dressed?

On the whole, I agree with you that it’s better to be a bit overdressed than to be underdressed. Nonetheless, it’s always best to “dress up” within the range suggested on the invitation, as people who are extremely overdressed or underdressed appear ill informed or perhaps ignorant.

“ Business Dressy” attire (for women) does not include evening gowns or that type of apparel. The word “business” implies suits, skirted or pantsuit styles. The word dressy means elegant or somewhat fancy. The combination, with business as a key word, still renders a different flavor from typical cocktail or formal evening wear for women.

With that said, I must admit to being suspicious of a high school reunion party requesting “business dressy” attire. It’s clearly not a business event, so it’s possible that there is a confused label that actually means “semi-formal” attire. Now why did I take that leap? Business dressy attire equates with semi-formal wear for men as both allocations dictate that men wear suits and ties. But for women, there can be a wide gap, which includes both classic business attire and dressy social wear.

Given the above concerns, I have two recommendations for you to wear. #1) a dressy pantsuit. #2) a dress (long or short style) that has a matching jacket. The jacket in both ensembles keeps you in the business dressy range, but gives you the freedom of removing your jacket after properly assessing what the other attendees are wearing.

The second step is to choose a fabric that makes a dressy statement, but one that is still somewhat businesslike. Wool crepe is such a fabric. From there, choose a rich color that looks terrific on you. The suit jacket, either for pants or a dress, could have some embellishment, such as beading or a fabric trim like velvet, leather, or suede on the lapel, collar, and/or cuffs. If you chose the pantsuit, add a blouse or top made of satin, lace, or metallic type fabric. The blouse or top can also have some sparkle to it, with a smattering of beads or sequins. If you plan on exercising the option of removing your jacket, be sure you like the way the dress, blouse, or top fits and looks when you’re not wearing the jacket.

For either outfit, choose elegant jewelry, such as pearls, diamonds, or other semi-precious stones or facsimiles. Avoid black-tie (ball gown) type jewels for this type of event, but your overall look should be quite dressy.

With either of these options, you can be confident that you will be dressed appropriately and that you will make a smashing statement. Enjoy!

Good luck to you,
Sherry Maysonave