I don’t know if it’s the start of Gossip Girl (YES!) or the autumnal promise of winter holidays, but for me, fall means new adventures—and in New York, that often means first dates. We have something of a dress code in Manhattan anyway (read: black) and, after recent talks with friends anxiously tearing apart their closets and bathrooms in search of the right date outfit, I’ve been thinking about what exactly makes such important and nerve-wracking nights go smoothly. My advice (to myself and others) when trying to impress without looking stressed: wear whatever you will put on and promptly forget you are wearing it. No one wants to be messing around with misplaced straps, peekaboo bra lace, tangled chains, or scratchy fabrics when focusing on much more important things over a strong martini. Easy beauty is especially vital when adrenaline’s high—to me, sexiness is embodied in simplicity.

The Bag
The bag is up there with the most crucial elements of date-night ensemble because it’s highly visible and needs to function. Personally, I prefer petite bags with handles: that way we don’t run the risk of awkwardly forgetting a clutch in a cab or losing our ringing cell phone in the bottom of an overlarge hobo. The grey Morning After Mini bag by Rebecca Minkoff pretty much sells itself, designed for exactly this type of occasion (all in the name): it’s small, classy, and in grey, provides totally fuss-free elegance. I also love the Lorca day-to-evening clutch by Hayden-Harnett ($335) for the same reason, as it works as both a tiny shoulder bag as well as sexy evening clutch. In grey, it’s understated and gorgeous.

The Shoes
All right, this is highly personal to everyone, but I’m a firm believer in wearing whatever you’re most comfortable in so there is no Carrie-style face planting on Houston Street. For heel girls, this fall’s hot thing are booties, and this pair of cut off booties from Loeffler Randall ($576 at Shopbop) look like strappy heels as much as boots. Perfect with denim or a dress—and in the grey I love so much more than basic black. And for taller gals with a more casual style, I cannot say enough about the Sloop ballet flat from French Sole ($95): I own them in black and I swear, I’m complimented constantly, and they are akin to wearing slippers. No problems with tripping or toe crunching, no fussy bows; just round-toed, Hepburn-style chic that disappears into the outfit.

The Main Piece
On a first date, there are pretty much two options: go for jeans or go for the LBD. Either way, make sure the piece looks relaxed. I own the Earnest Sewn Harlan jeans ($178) and love them because Earnest Sewn is masterful at making elegant cuts with an American edge: chill, a bit rustic, not too polished or schmancy, but obviously expensive (which they unfortunately are). These skinny black ones are exactly right for an evening out. On the dress front, for fall I like this Turtleneck LBD from Mint Jodi Arnold ($385): it’s very simple and classic with a weird twist in the ultra-high neck (also helps hide the blushing when things go well!). This works with a cardigan or leather jacket, and alone in a warm restaurant.

The Face
The final touch—the makeup—should not be neglected. I believe Tarte has the solution to every problem when it comes to rushed prep time with big results required. I could leave the house in only these two products and feel like Heidi Klum: the Lock & Roll eyeshadow ($17) promises to be crease-free and IS, requiring a simple brush-on and finger-dab and all-night shimmer fit for Titania. The natural swirl cheekstain ($28) pretty much does the same for glowing, dewy cheeks.

Photo courtesy of Store Adore