Evening appropriate

When I get married, it will be to a man who knows me well enough to propose with a custom-fit black cocktail dress, not a ring.

This asymmetrical rosette-trimmed frock from 3.1 Phillip Lim (right: $485 at net-a-porter.com) not only costs a fraction of a what a diamond would but also captures "Will you spend the rest of your life with me?" in a much more meaningful, much more Johanna-inspired way.

Some women are at their most powerful in lingerie, some in gym clothes, and others in fitted business suits. For me, that one article of clothing that makes me feel as insightful as Eleanor Clift, as classy as Grace Kelly, and as alluring as Monica Bellucci is the black evening dress.

A satin mini with Dolman sleeves, a Roland Mouret-style wool shift (left: Jackie O dress by Black Halo, $285 at activeendeavors.com), a strapless tea-length bubble-hemmed gown with Chantilly lace trim at the bust -- I love them all equally.

Well, maybe the last one a little less, but that's just because I like to show as much leg as possible.

This leads me nicely into setting the ground rules for a sophisticated evening look. Almost identical to the guidelines I laid out yesterday for casual outfits (dress for your audience, be age-appropriate, don't wear anything too tight, too short, too sheer, or too forcibly trendy), evening wear has but one critical addition:

Identify your body's strengths, works-in-progress, and weaknesses, and dress accordingly.

Case Study: the Strapless Dress

I've been waiting for an opportunity to rant about an offense I encounter every time I attend a wedding or walk through Georgetown during graduation party season. No, I'm not talking about drunk 60 years olds hitting on me, I'm talking about women who haven't earned the right to wear a strapless dress flagrantly doing it anyway.

Contrary to what most brides think, a strapless neckline - straight or sweetheart - is not universally flattering. In fact, I think it's one of the most difficult to pull off. Yes, I did notice 2/3 of the women at the Golden Globes shot this look and scored, but I also know that a major part of a Malibu Barbie's day is spent sculpting her shoulders and back for the sole purpose of always looking red carpet ready. It's not just about being thin, it's about being toned. But not too toned, or else you risk looking like a wrestler. Jessica Biel, in my opinion, doesn't look as good in a strapless dress as she does in any other style; her muscular upper body overpowers the rest of her when it's fully exposed, making her look much more masculine than she does even in a string bikini.

If your shoulders, back, and arms meet the standard, the last consideration is the chest. Your ladies need to be large enough to hold up the gown but not too big that they pour out the sides and overflow Salma-style at the top. How many women do you know who have thin, toned, shoulders, back and arms in tandem with a B/C-cup?

I don't, either, but for some reason, every time I attend a party, I meet nice women who I know would never display their muffin-tops in jeans and a crop-top, yet there they are, in formal settings, baking it up at eye-level in front of hundreds of people.

I could go through every permutation of neckline and hemline possible on a cocktail dress and/or evening gown and offer my opinion on what type of body looks best in each, but I already know my bottom line will always be the same: among the dresses that flatter your strengths, choose the one you like the most.

I think deep-down all of us know that it takes thin muscular legs to wear a mini, it takes perky symmetrical breasts to do a deep v-plunge, and it takes a thin-as-Molly-Sims frame to wear an empire waistline and not look pregnant.

I believe the everyday woman's failure to choose the right evening dress is not due to fashion ignorance but rather a refusal to accept the fact that the dress she loves highlights her weaknesses instead of her strengths.

But if she loves the dress enough, she'll hit the Washington Sports Club five days a week, eat more sensibly and turn that weakness first into a work-in-progress, and ultimately, into a strength. If a Hollywood starlet can do it, a DC lawyer, intel analyst, and Hill staffer sure as hell can, too.

In the course of writing this post, I decided that in my ideal proposal, in addition to the 3.1 Phillip Lim dress, I'd also like a pair of shoes to go with it. These patent leather D'orsays from Prada ($495 at saks.com) will do just fine.