Dress for Sex-ess: A Guide to Looking Like a Serious Goddess on Each and Every First Date

Joke, the title is a joke. I would never advocate for sex on a first date. (Although nor would I condemn – it’s your world, lady…)

At any rate. It may be that the onslaught of online dating means you go on some first dates that you’re not totally stoked on. And it may be that when you’re 33 and still going on first dates you don’t necessarily expect to be stoked anyway. But as I see it, a first date is still a first date and a few things are going to happen:

1. I’m going for drinks (not coffee dude) – not dinner.
2. The drinks are going to be paid for by the gentlemen (this rule ONLY applies to the first date in my book, but it’s hard and fast: if the man accepts my offer to pay, he’s not getting a date #2).
3. I’m going to put in some effort to charm and entertain, not just because it’s a first impression that forms the foundation of a potential “something” but because I think that’s the respectful thing to do when a stranger takes the time to meet up with you.

And that third point flows into how I put myself together for a first date. And because I’ve been doing it for enough years, I have a pretty standard formula for success.

The overall look: Effortlessly put-together evening casual.

What is evening casual? It’s a definitive step-up from jeans-day-Friday and absolutely not any evening look a Real Housewife would select.

I start with my favorite and most flattering pair of jeans. Personally, I discovered my best-fit years ago at a little place that both I as well as legions of middle-American teens both enjoy – American Eagle.  I love the Jegging Ankle, which runs you a steep $29.99 when on sale, which 9 times out of 10, they are, because hey, when you live on allowance, that’s your budget.

I pick a top with great fit and drape that works for my figure and has some level of visual interest (a pretty fabric, an interesting neckline) but isn’t distracting or overdone (backless…sequins…crazy prints).  I like to show off my manly shoulders and tan arms, so I typically go with a tank. In particular, I like neutral solid colored tanks that I can accessorize, like Joie’s silk tanks. If you’re a boob girl, show a little bit of cleave (not all your cleave). If you fear the bat wings, go with sleeves, but ensure it has some shape or perhaps a more open neckline.

I like to go with a sexy shoe. Subtle sexiness. Not exotic dancer sexiness. I’m not opposed to the stripper shoe look, but they’re not first date material. I go with a mid-level heel, and typically I pick one that has a classic silhouette but adds a pop of color. Just ordered these classic pointy-toed pumps from J. Crew (in fresh strawberry) and they’ll absolutely be plucked out for yet another first date, I’m sure. Hot summer? Try a moderately-heeled sandal – as long as your feet are prepped for exposure (no chipped polish, no oozing blisters, no icky flaky skin). Cold winter? Great boots (neutral color; no pleather; not overly trendy). Personally I think heels, even if they’re low, are the way to go. Even if you’re tall. They’re just more flattering.

Those are the foundational pieces. From there, it’s about layering elements that make it look thoughtfully pulled-together (but not overwrought or overdone). For me, these are the details that let your individual sense of style shine through.

I have a great new jacket that I’ve been wearing every chance I get. It’s a military-style jacket from G-Star in a neutral color that has strong detailing and adds some edge and contrast to a silk tank and ultra-fem heels. Jewelry-wise, I’m personally into a more-is-more approach – I like to layer a lot of pieces in both gold and silver that are complementary but eclectic – often purchased on trips or from small hole-in-the walls places – stuff that no one else owns – it’s all me. Point is, choose pieces that demonstrate your own style, not someone else’s, not only tied other trends of the moment.

Being pulled-together extends into tasteful makeup and hair. Stick to neutral shades and light applications that make you look approachable and touchable – not like a little china doll. Even if you’re into a bright lip or dramatic eyes these days, leave them behind on a first date. Dramatic makeup is for pea-cocking to other women – they don’t show off you for you, and dudes tend to find heavy makeup frightening. Go with hair that looks clean, shiny, healthy, simple. Hair that you can run hands through. Not that anyone will run hands through it, but, just you know, if the opportunity arose, hands wouldn’t stick in curls and sprays. And by the way – it’s biology that guys dig hair – thick, long locks are a sign of fertility. So I wear mine down for at least 5 minutes…then I tuck it up into its preferred bun.

There you have it: perfected first date dressing fully dissected, from the foundational pieces to the layers and details that bring it together. The rest – witty commentary, smart debates, flirtatious banter, avoiding over-imbibing, finding the it-factor…all up to you, my friends.