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Click through to see what happens when a handful of Lucky editors invite the main men in their lives to pick out their head-to-toe Valentine's Day date night looks.
Deputy Editor Leigh Belz Ray and Husband Kevin

HIS: "Leigh has the luxury of being a statuesque brunette, which means she’s equally gorgeous and comfortable in jeans, a James Perse v-neck and some Flyknits as she is in a flirty, feminine kit. For something like Valentine’s Day, I imagine she’d opt for the latter.

I started with the dress. She’s very fond of Rag & Bone and this cocktail dress is sexy with the splash of color that she always enjoys. She’s also very fond of dresses with pockets. So two birds with one stone and all that. She doesn’t feel terribly comfortable in proper heels for long stretches of time, and I love her in boots with a bit of a heel, so I’ll go there next. Alexander Wang is one of her favorite brands, so it’s a safe enough bet to pick something from him. The Anouck Chelsea boot is a great silhouette and this color has a little shine on the black. She looks cute with a big bag, so even though she might not need all this space for a date, I’d give her this Mulberry Bayswater in a nice gray. Leigh isn’t fond of particularly logo-y stuff, but I personally think this little Chanel necklace is fun and would look nice on her. So I’m picking it."

HERS: "There's something very reassuring and 'me' about a shift dress. I love this A.P.C. piece because it takes the simple shift and makes it a little more interesting with the v-slit neckline, front breast pockets and ever-so-slight flare. It's a super versatile piece that can be dressed up for special nights (like Valentine's Day) but also could work in the office with a blazer and tights. But for Valentine's Day, I think there's something romantic about a mostly black/white/red palette, so this great dress is the perfect foundation. I'm very ready for spring, but it's still extremely cold here in New York City. So cute outwear remains a must. For Valentine's Day, I'd love to cover up with this jacket. I dig the silhouette and wide-cropped sleeves—they add a little shape to my look, since the shift I picked is essentially straight up and down.

Jean-Michel Cazabat is one of my favorite shoe designers: his pumps just feel next-level sexy to me. And they manage to be comfortable too — which means I can wear them all night and actually focus on Kevin instead of throbby feet. I covet this grey lizard print—it goes with everything! I'm definitely a bag and shoes kind of girl. They have the ability to get me excited like nothing else—and they're where I'll splurge a little. I first saw this iPad clutch when I was looking through Cellairis' amazing new Lily Kwong Collection collaboration line…and I've been obsessed ever since. Not only will I use this to transport my iPad, I plan to use it as a night-out clutch as well. I love the soft brown pony hair and the little peek of the red suede lining. It adds a little fun to any outfit, including my Valentine's Day look. I keep my jewelry look pretty simple, but I'd love a little pendant to peek through the v-slit neckline of my dress. R is not only my married last name, Ray, but is also me and Kevin's new daughter's first initial. (She's Riley Ray, so a double R.)

I like a red lip even on a not-universally-romantic night so on Valentine's Day I'm of course going to go red. MAC lip pencils give a great saturated color, so I know it'll last all night. I'll continue the red theme on my nails. I can't decide if I want to go with a shiny red or add a little bit of sparkle. It'll be a game-time call. I'm pretty specific about perfume — I've essentially worn one scent for the past ten years. Until recently, that is. I met the lovely Leilani Bishop in Venice, California and am a new convert to her amazing fragrance oils. My favorite is Pikake—a beachy musk that instantly relaxes me. Kevin's pretty observant, so we'll see if he notices something different on Valentine's Day."

Senior Digital Editor Elana Fishman and Boyfriend Ryan

HIS: "Elana has a very particular style. I can't imagine her showing up for anything wearing jeans and a t-shirt, for example. In a way, that made this easy for me. I picture her wearing an outfit like this, which to me is a little bit French fashion and a little bit Zooey Deschanel quirk.  Before we first met, I saw a picture of her trying on an A.P.C. jacket in my best friend's store. That first impression stuck with me (it's the picture for her in my phone), so I had to include this coat. And I love nights when she carries a bigger bag, like this one, because it has room to hide an adult beverage or two when we go see a movie."

HERS: "I don't know if designer Guillaume Henry possesses some sort of bizarre magical power, but I never feel prettier than I do when I'm wearing a Carven dress. So this one, with its full skirt (an Elana necessity) and very V-Day-appropriate lace insets, was a no-brainer. Ryan loves it when I wear heels, but since we're exactly the same height (5'10) and I like being on even footing with each other, I usually wear flats when we go out—plus, comfort! These J.Crew smoking slippers fit the bill perfectly. I picked two pretty little pieces of jewelry from Catbird, my favorite jewelry store—at this point, Ryan knows he can literally walk in and pick anything in the shop and I'm guaranteed to love it. My New Year's resolution this year was to read more books—and my guy takes resolutions very seriously (his is to run the New York City Marathon), so he loves to put on the pressure. I feel like this gorgeous Olympia Le-Tan novel clutch sort of pokes fun at my goal—in addition to being beautiful, of course. And no, I haven't read Rilke's Edelweiss. Oh well."

Social Media Director Virginia Nam and Fiancé Jason

HIS: "Virginia enjoys being flashy in small ways. She won't wear anything emblazoned with tacky logos or names, but she loves wearing shoes that grab your eye. She also has a fondness for accessories that reflect her tough personality—items that warn you not to be fooled by her small frame. Comfort and warmth are essential for her, but they always take a backseat to style."

HERS: "I like to combine ladylike and tough items together. I picked the Preen dress because it's a pretty silhouette that (I think) my fiancé would like. The dress alone is a bit too girly for me so I wanted to offset that with the biker jacket. Up until now, the outfit is pretty standard so I would add the Sophia Webster heels and checkered Charlotte Olympia clutch to inject some personality and fun."

Associate Digital Editor Alison Syrett Cleary and Husband Patrick

HIS: "I tried to go with the names of places I knew that Alison liked, or remembered going to in Paris, because it would be a nice touch to include our honeymoon on a day all about love. However, I think I might have too many moving parts here. Does this outfit make any/enough sense? I'm not sure if I made a cool V-Day outfit for her or just one that every 14-year-old girl would wear to a vampire prom."

HERS: "So long as it doesn't affect my comfort, I'm all for dressing a little sexier than usual on Valentine's Day. This dress is exactly the type of thing I would look for while V-Day shopping since it's figure-flattering but not in a tight waisting-cinching way that means I can't partake in every course on the prix fixe! My husband knows that would kill the date anyways—I'm no fun when I'm hungry!"

Senior Fashion Writer Jayna Maleri and Husband Jon

HIS: "Jayna has great style and she's not afraid of mixing elements that you wouldn’t expect to work. She always pulls it off. She says I like when she dresses like a little man, but I just don’t like high-heels or anything that looks difficult to wear. I was trying to recreate an outfit she tried on when we were in Bologna at a store called Neirami. These pants look similarly fun to wear. I guess there is something Charlie Chaplin chic about it, but more feminine."

HERS: "I tend to dress pretty casual, and always comfy, but it’s nice to go a little more glam and a little more sleek every once in a while. This outfit my version of both of those things, but it still feels very much like me. My husband will HATE that I chose heels, but too bad for him, because heels rule. Happy Valentine’s!"

Digital Fashion News Writer Maura Brannigan and Boyfriend Matt

HIS: "When approaching the idea of creating Maura's ideal outfit, one needs to blend together conflicting themes: dress her as if she were a six-year-old while still being trendy. With that, the first thing that came to mind is some sort of buttoned-up, white dress with either an element of lace or florals. She has an affinity for pumps, and since we're talking V-Day, they may as well be red. Throw in a matching-color clutch and you're good to go. Note: I think these are different reds, but I've made it this far, so let's just go with it. Also, let's just be honest, a clutch is all a lady needs—she shouldn't be paying for anything. Chivalry is not dead, America."

HERS: "I tend to favor schoolgirly dresses and skirts five out of seven days out of the week. To that end, a pink dress (I own almost no red) is a natural pick for me on Valentine's Day—which is especially fortunate considering the majority of my closet is comprised of blush and coral shades. I'm also not huge on showing a ton of skin (whether Matt likes it or not...), but a dress that's shorter and perhaps a little tighter above the waist would be fitting for something sexier. And finally, pink and black is one of my favorite color combinations, so a mix of slightly edgier, black leather accessories and minimal, pretty jewelry will do the trick."