Big Night Out

When I was little, my father took me to the Kennedy Center for symphonies and other performances on several occasions. I remember one in particular — perhaps my first? I must have been five or six, and nothing in the world seemed more sophisticated or glamorous. My mother dressed me in a “party dress” (anyone else remember having frilly socks and patent leather Mary Janes also dubbed “party socks” and “party shoes”?) she and my father had brought me back from Paris that summer. It was green and white striped with little balloon sleeves and a green sash. My mother spritzed a little perfume on me and, as I headed down the stairs, my father said “Ooh la la!” That sealed the deal. I was officially in love with the way that dressing up and heading out for an evening made me feel. I was head over heels with the drama of a Big Night Out. Whether it’s the opera, a black tie gala, or an uber-formal wedding — yes, please.

And while these to-dos are sadly few and far between in this day in age, a girl can still dream. Ideas for a future Cinderella-at-the-ball moment? It all begins with a formal dress. And if we’re talking fantasy, I’m going to reach for the Big Guns: Valentino. This one-shouldered black gown is the stuff of legends ($6,990, Neiman Marcus):

Then a classic Judith Leiber minaudiere ($2,995, Judith Lieber) and some faux cils:

Add some dramatic lace Valentino pumps ($895, Nordstrom) and a fistful of diamonds. Insta-Cinderella.

Of course, some of us have to contend with the real world and issues of affordability (myself included), so let’s shelf those over the top dreams and look for ways to get the look in more realistic terms. I’m pretty much obsessed with this Aidan Mattox one-shouldered evening gown ($385, Neiman Marcus) — I stumbled upon it in my search for a white dress to wear to my rehearsal dinner (don’t worry, I won’t be wearing full-length — or anything quite so formal — but it caught my eye):

Adore. Can you imagine pulling your hair up, adding some sparkling enorma-studs (below, Ylang23 Vintage — $170, Ylang23), and heading out for the night? You’d be the belle of the belle.

I’m partial to the design of the above earrings because they remind me of the spectacular lighting on the ceiling of the Kennedy Center opera house:

Love the drama. Pair the above gown with these off-the-charts t-straps by Louboutin ($1,995, Barneys):

I know, I know. Shame on me. I said I’d try to stay within the realm of reality, but — how can you resist? You could also pair the dress with some unfussy heeled silver sandals. Stuart Weitzman’s Delovely heels are pretty much the most classic evening shoes you can own ($285, Zappos):

If you owned a pair in gold and silver, you’d pretty much be set for life. And maybe it’s because I’m getting married this August, but this Grecian goddess gown in ethereal white has me at hello (BCBG, $214, Saks):

The same goes for this jaw-dropping Notte by Marchesa gown (on sale for $440, The Outnet):

LOVE. And Marchesa is the premiere evening-wear designer du jour — favored by Rachel Zoe, it’s the most coveted label of all at the moment. Add this little eye-catching bag to either gown — fireworks in clutch form! — by Whiting and Davis ($125, Endless):

And some chunky danglers — I’m partial to this clustered, knotty pair by J. Crew ($65, J. Crew):

They’d look equally stunning with this simple black bustier dress by Ports 1961 (on sale for $455, Shopbop):

Pair with some killer shoes — either champagne or kicked-up black will do the trick. These Stuart Weitzman’s look lovely and sort of vintage in the “Misty” color ($325, Shoebox):

However, if you’re an all-black kinda gal, these Sergio Rossis caught my eye in the Saks sale section ($482, Saks) — very Carrie Bradshaw in my mind:

Consider pairing with a structured clutch — Amanda Pearl’s are to.die.for (the one below is from last season, but she has lovely new versions for this season), but they are an investment ($1,595 apiece).

Alternately, try this flashy little Felix Ray soft-sided clutch (comes in a few different colors and similar styles — $220, Felix Rey):

Up the ante with this gorgeous, glitzy chrysanthemum ring ($175, nOir jewelry — my go-to for fun, unexpected cocktail rings, which are kind of my signature):

If you’re not into the oversized ring look, or if you want to appear absolutely dripping in jewels, add this crystal link bracelet ($125, J. Crew):

Into the super-femme look? Test drive this 1970s chic Halston Heritage gown ($455, Shopbop):

Pull out all the stops with these show-stopping swarovski crystal studded peep toes by Rodo ($880, Forzieri):

Definitely glass slipper status. You could add this chunky pearl Lee Angel ring to further beef up your heavenly angel look ($66, Shopbop):

I’m also kind of enamored of this clustered pearl-and-pink stone ring — the wiring accent adds some interesting edge ($114, Couture Candy):

If you’re into the pearls (very opera house), I like the idea of a drapey black dress (this Ella Moss “Haze” Dress — on sale for $114 at Saks — could be lovely):

And add this lovely little pearl-encrusted clutch ($50, Aldo):

And because nowadays you can get away with shorter dresses in the evening, consider this lovely navy-and-black Adam Lippes number (on sale for $289, Adam):

For some reason, navy-on-black bespeaks subtle sophistication to me. The artful folds of the dress above really transform the dress into something novel and unexpected. Don’t you die over it? This full-skirted, asymmetrical mini by Thread Social is also evening-ready, despite its abbreviated hem (on sale for $325, Thread Social):

The sparkles and length keep it youthful, but it’s still romantically elegant. And now — if you want to relive a moment of true movie magic — let’s take our cues from Julia Roberts in Pretty Woman.