Tim Gunn: How to Dress for a Big Night Out

It's fascinating to me that dressy evening events — cocktail receptions, charity galas, premieres — elicit such excitement of anticipation, yet so frequently disappoint from a fashion perspective. Why is it that so many people choose eveningwear that is lackluster? I write choose, because it is a choice. If you want a look that's humdrum, then, OK, accept responsibility for wearing it. But I find it hard to believe that all of those humdrummers out there are really satisfied with their look. In most cases, people are simply in a fashion rut. Here's how to get out of it:

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Handbags

Why, oh, why do people persist in dragging around luggage-size handbags to evening events? I see this with more frequency than I care to recall. What are people thinking? Do they line these behemoths with plastic in order to escape with leftovers? There is an easy prescription for getting this right: The dressier the affair, the smaller the handbag. I want to sing the praises of the clutch style, which comes in dozens of iterations. The clutch is precisely that — a handbag that one clutches. My advocacy for the clutch has caused some women to balk: "But what do I do during a cocktail reception?" You place the clutch under your upper left arm with a cocktail in your left hand. This leaves your right hand free for greetings.

Legwear

There is no simpler way to be on-trend this season than to don a pair of fashion hosiery. They are loaded with glam and pizzazz, and I can think of nothing easier — and more affordable — to lift the spirits of a basic black cocktail dress than these shimmering, sparkling, or iridescent newcomers. Furthermore, I believe that when one is wearing stockings, one should look like she's wearing stockings (few things offer more dowdiness than sheer hosiery). I rarely state that a particular item provides something for everyone, but in this case it's true!

Cover-ups

Forget about global warming; just plain ol' air-conditioning and heating are enough for me to salute the benefits of layering. But let's banish the pashmina, please, and consider some alternatives. You can play it safe with a dress or skirt with a matching jacket, but I want you to consider the evening cover-up an opportunity to have some fun with a novelty item, like a metallic gauze stole or an embellished cardigan, or a plain cardigan in metallic wool, cotton, or silk. (Warning: Don't combine any of these with fashion hosiery or risk being mistaken for a float in a parade.)

Apparel

It goes without saying (so why am I?) that the basic black dress is the core of evening attire. It provides a neutral platform for accessories. But I want to suggest separates as well. Think about the impact and fashion counterpoint of a pencil skirt paired with an exuberant white top. Or how about a fitted bustier with a voluminous skirt? There are limitless options. Just take a chance!