What to Wear…And When

By Abby and Elle

Evening dress by Tadashi Shoji

Evening dress by Tadashi Shoji

So you have an event to attend, but you’re unsure what to wear. Naturally the answer depends on the what, when and where. For instance, if you will be attending Cleveland Fashion Week’s Black Tie Gala and Runway Show this coming May, you best not show up in your jeans (even if they do have jeweled embellishments). But if you’ll be attending a wedding on the beach on a July afternoon, then a sundress will work splendidly.

There is a dress code for every reason you can possibly have to leave the house. Let’s start with the most formal:

  • Black Tie: This type of affair is the most demanding, but you’ll still want to look fabulous, yes? Wear an evening gown or classic-style cocktail dress. Strappy heels are a must, so make sure you valet park or have your beau drop you at the door. Dig out your most expensive (or expensive looking) jewelry. And leave the big bag behind for cripe’s sake. Grab a clutch instead — you know the kind: it holds a driver’s license, a tube of lipstick, and a twenty-dollar bill. Nothing more.
  • Formal: While similar to black tie, you can be more relaxed. For example, instead of an evening gown, choose a cocktail dress. Don’t be afraid to be daring here: Have fun with funky styles, colors and cuts. Try mixing it up by pairing vintage jewelry with a trendy dress; combining textures such as tulle with faux fur; or pairing a conventional piece with something flirty.
  • Dressy Casual: To our minds, this is the most difficult to pull off. Think of it like you’re going to your office job, and then replace one of the pieces with something more casual: Khaki pants and an oxford shirt; flouncy skirt and dressy T (sans hose, of course); colored denims (i.e., not blue) and a blouse. Anyhow, don’t make us belabor this point. We hold dressy casual in disdain and, besides, you get the picture.
  • Casual: Pull out those jeans and whatever else you want to pair with them. Crisp white oxford? Chunky sweater? Almost anything goes. But save the sweats and yoga pants for sleeping, lounging around the house or going to the gym.

Follow these Two Rules of Thumb: 1) Try not to look like everyone else, so keep an eye out for a fresh design that you can be comfortable in; and 2) Better to overdress than underdress. Why? Because the better you look, the better you’ll feel. Plus, as Nina Garcia writes in The Little Black Book of Style, the better you look, the better you’ll be treated. We couldn’t agree more! Dress like a princess, and you’ll be treated like royalty.

Says Abby, “I wish I had known this several years ago when I attempted to attend a bridal fashion show. My then-fiance and I showed up at a country club in jeans and T-shirts. We were wandering around from building to building because we had no idea where this event was actually taking place. Finally we ran into a crowd of well-dressed people. Just then one of the wait staff asked if we were lost and if he could help us … leave. I was so shocked I started to cry, and, worse, I nearly fell down the stairs because the tears blurred my vision.”

Well, let that be a lesson to all. So if you’re ever stumped about what to wear to a special occasion, don a little black dress. As Karl Lagerfeld so aptly said, “One is never over- or underdressed in a little black dress.”

PacificPlex peacock cocktail dress

PacificPlex peacock cocktail dress

Evening dress by Tadashi Shoji

Evening dress by Tadashi Shoji

Cocktail dress by Zac Posen at Neiman Marcus

Cocktail dress by Zac Posen at Neiman Marcus

Cocktail dress from JJ's House

Cocktail dress from JJ’s House

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