Valentine’s Day: February 14th — Cupid’s day of reckoning. A 24-hour stretch during which the winged archer — also know as the mythical Greek god of love, Eros — flutters about mischievously igniting love’s passion between mortals, whilst inhaling the mix of pheromones and roses hanging in the air.

And while all are invited to join the champagne celebration in honour of Cupid on his special day, the fine print requests one “bring a date.” Cue the mad rush to the nearest flower shop, chocolatier, lingerie boutique, or for the lucky lot, Tiffany & Co., all in preparation for an evening of peacocking and courting.

As couples — new and old — plan grand gestures and plays of affection — they also must find the perfect outfit to be adored in; a head-to-toe look that at its best suggest just what sort of gift matches both their ensemble and their heart’s desire. Below, our style guide to dressing for the occasion…and the gift.

For girl-next-door types who prefer voluminous a-line skirts and anything with a Peter Pan collar, this particular mash up of clothing items will keep you snuggly in your comfort zone, while also flirting with your edgier side.

Valentine’s Day is all about illusions, and Zara’s faux leather skort is trickery at its most stylish. The asymmetrical overlapping leather conceals the fact you’re wearing shorts (necessary considering the short length of the bottom), all the while flaunting your sexy. Remember the hem line? We suggest pairing the piece with plain black tights – opacity dependent on mood and desired effect.

What’s on top? A girly printed sweater that embraces all things sweet. Our pick is from Lord & Taylor 424 Fifth, Hudson’s Bay Co.’s new women’s private-label brand. The mod floral print pullover from the line is just the super feminine top a more daring bottom demands when piecing together a Valentine’s Day date look for a woman who has an enduring penchant for bows.

Now for what to wear underneath. Skip your average patch and string of lace, and opt for a more modern and alluring choice in undies from Fortnight Lingerie like the Lyra bandeau set shown above. Or for something more classic, go for L’Agent’s Danita bra in red satin. Designed by sisters Penélope and Mónica Cruz in partnership with the British luxury lingerie label Agent Provocateur, the undergarment is part of the  brand’s spring/summer 2014 collection, inspired by fashion photographer Helmut Newton’s iconic lingerie shoots.

To complete the look, move on to finding the perfect accessories. Try Pour La Victoire’s Alsace cross-body bag — after all, the bow and arrow emblem may just be lucky on Cupid’s day. And lastly, literally polish off your look with a coat of Deborah Lippmann’s “Just Walk away Renee” (created in collaboration with actress Renée Zellweger). The nail shade will serve as a reminder that you do not belong in Bridget Jones Diary. You can always walk away in your Rag & Bone Harrow boots — boots made for walking…and flirting.

As for what your sugar and spice date outfit will inspire in the realm of gifts, you can trust that your modern take on the signature Doris Day look will translate into a present with fairytale appeal. Time to start dropping hints about Tiffany & Co.’s Tiffany Enchant collection. For the stylish girl-next-door, we envision a pair of Tiffany Enchant heart earrings wrapped up in a little blue box.

If chains and whips excite you like in Rihanna “S&M” track, you may want to rein in your flair for  playing the dominatrix for at least the dinner portion of your Valentine’s Day date, especially if it’s a new Mr. Right [Now] sitting across the table.

Looking sophisticated and feeling sexy are not opposing style designations; they can easily go hand-in-hand. If Mrs. Robinson-at-the-club is your fashion M.O., try on a look that more subtly flaunts your feminine prowess. Define your silhouette in a body hugging dress by Pink Tartan (above). The pale pink shade is soft and girly, while the formfitting tailoring of the piece is polished while sultry.

Continue to tease in designer Pamela Mann’s signature love seamed tights (available in natural and black), best worn when the back seam sentiment is read above a comely pair of AnnTaylor’s Juliette ankle strap heels in black.

And let’s not forget the fun part. Stay true to form underneath it all dressed in Fleur du Mal’s lace bondage triangle bra and panties. This matching set of intimates will send hearts racing, as fast as any femme fatale could hope for.

Next, match the look with a classic bag that shows off modern sensibilities like the PS1 Pouchette in black leather by Proenza Schouler. Finally, finish off your look in a shade that is only to be expected of a vixen such as yourself: red. NARS Jungle Red Semi Matte Lipstick will render lips irresistible come time to say goodnight.

Bad girl though you may try to dress yourself up as, gifts that are sweet and simple go straight to your heart. This chilled out temptress look is a mismatch for leather panties, but the perfect fit for a variety of Valentine’s Day gift every girl’s heart would skip a beat for: In God We Trust NYC’s Sweet Nothing Necklace, available with custom engraving. Can you say, “Awe?”