12 Date Night Outfit Essentials

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Whether it’s your first date or your 50th, pulling together a date night look can be exciting. But more often than not, a little inspiration is needed when figuring out where to go and, of course, what to wear—especially if you’re feeling slightly overwhelmed by your closet.

Jami-lyn Fehr, founder and CEO of Modiste, will always run the risk of being “too dressed up” when it comes to dates. “I take every opportunity to dress up, and I’ve never felt uncomfortable with the idea of being slightly overdressed,” she tells Bazaar. “Date night gives me a reason to pull together an outfit that both flatters my figure and nods to my personality!” Fehr doesn’t let a relaxed setting stop her from adding a bold accessory. Even if she’s opting for her brand’s simple cashmere top and vintage jeans, she’s adding a pair of heels for extra confidence. When she’s feeling particularly daring, Area and Blumarine are her go-to brands for their signature sparkly pieces.

Our date night guide below features three phenomenal restaurants with corresponding date night looks. Whether you can make it to one or not, we hope the accompanying looks help spark inspiration for your next night out.

Glamorous Details at Drusie & Darr

Nashville, TN. Experience fine dining like you never have before at Drusie & Darr, celebrated chef Jean-Georges Vongerichten’s debut in the American South. Fehr, a Nashville resident, is familiar with the glamorous restaurant’s artful interior and modern menu. “I was so thrilled when it was announced a Jean-Georges restaurant would be opening in Nashville several years ago,” she says. “Outside of the food, it’s got the most stunning interior design.”

Located inside the Hermitage Hotel, the restaurant has a storied dining room that features a simple palette of leather, metal, wood, and stone; decorated with lamps made from mother-of-pearl and bespoke curved banquettes. According to Fehr, the restroom interior is as beautiful as the main dining room, and she suggests stopping inside without a reservation, even if just for a Instagram photoshoot. If you’ve been looking for an excuse to dress to the nines, this is your date night spot. Whether you’re celebrating an anniversary or nothing at all, we suggest a sleek maxi dress and sultry high heels with soles that match a striking red lip.

Betty Maxi Dress

“Anna October’s dresses are the epitome of femininity! Somehow, her understated silhouettes flatter every body type, and I always feel my best in one of her pieces,” says Fehr.

The empire waistline of the brand's Betty maxi dress is so classic, and the simple colors make styling it so easy.

Confession Lipstick Red 0

This is the perfect date night lipstick. The creamy, satin finish on this red hue instantly draws attention to your lips, and can add a pop of color to an otherwise simple fit.

Rosalie Leather Red Sole Stiletto Sandals

And while red lipstick is sexy, we'd argue that red soles are even sexier. These strappy Christian Louboutin’s should be your go-to for formal dates. If given the chance, Fehr will always choose a similar option. “Heels give me confidence a flat can’t quite provide, especially if I’m on a first date.”

Jardin de Peggy Pearl & 14kt Gold Necklace

What’s more classic than a string of pearls? Wear them layered around your neck or at full length to highlight the delicate beauty of each freshwater gem.

Lush Pink Interiors at Contessa

Miami, FL. Take a trip to Lake Como without leaving the States at this glamorous, old-world inspired restaurant. As you step inside the lush two-story space at Contessa, expect to be blown away by the rich designs, from pristine marble floors to dreamy chandeliers. This dining destination is seated in the heart of Miami’s design district, so don’t expect to see your fellow patrons in anything but their best cocktail attire. With a vast menu of traditional Northern Italian cuisine and classic cocktails, choose a colorful look to match the vibrant, energetic atmosphere.

Fortuna Dress

It would be best to keep Miami’s party scene in mind for this date—you’ll want to wear something to dinner that can also transition into a going-out dress for the afterparty. This darling Emilia Wickstead mini is just as beautiful with a pair of chunky heels as it is with a pair of sky-high stilettos.

Lennox Tennis Bracelet - White Gold

Melissa Kaye’s Lennox Tennis Bracelet is simple but luxurious. It will catch the light beautifully without feeling too in your face.

Tabi Pumps

While Margiela's Tabis aren’t everyone’s cup of tea, if you love the split-toe shoe, you can't go wrong with these block heel pumps. Made from soft nappa leather, these are the perfect neutral option that adds a little quirkiness to any look.

Bambinou Small Padded-Leather Shoulder Bag

Carrying Jacquemus’s padded shoulder bag in a fitting sky blue is as close to carrying a cloud that most of us will ever get. It's big enough to hold you phone, wallet, and lipstick but also small enough to fit comfortably under your arm or around your shoulder.

Outdoor Dining at Twenty Three Grand

Manhattan, NY. Set beneath a state-of-the-art, retractable greenhouse, Twenty Three Grand is an oasis in the middle of SoHo. Enjoy brunch, lunch, dinner, or just cocktails in both the indoors and outdoors. The menu features global flavors with a Mediterranean flair; feast on everything from fried olives and tuna carpaccio to angel hair pasta and prime rib burgers. Casual but elevated pieces are ideal for this eatery, as you’ll want an outfit that fits both the vibes of the green-filled terrace and the cozy bar. For outfits, think white waistcoats, wide-legged trousers, and a classic handbag that matches the deep teal booths you’ll be sitting on.

Vest with Rose

One of Fehr’s top brand picks when she’s looking to be bold is Blumarine. Even its basics are decked out with playful details, like this Vest with a rosette in the middle. Make the statement style more casual with informal bottoms—Fehr suggests pairing elegant tops with vintage Levi’s for a more effortless look.

Bottega Veneta

This iconic Intrecciato Bottega Veneta bag is made even more special in this rich, teal suede. If you’re looking to expand your wardrobe from only neutrals to more color, use this as a starting point.

New Didi Wide Leg Trousers

Khaki, wide-leg trousers are a must-have for any wardrobe. Easy to wear to the office with a blazer or to a date with a chic crop top, you’ll get so many wears out of these by TWP.

Vienne Mule - Blanc

A necessary addition to your shoe collection is a pair of flat mules. We adore these ones by Alaïa. They'd look just at home on a beach as they would in an office—or on a hot date, of course.

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