When it comes to date night, choosing the perfect outfit can be as exciting as the date itself! But with so many styles and occasions to consider, it can be tricky to know what to wear. The key to a memorable date night isn’t just the location or the activity, but the way you both dress for it. That’s why we’ve put together some matchup date night outfit ideas to inspire your next night out (or in). Whether you’re dressing up for a fancy dinner or keeping it casual for a laid-back date night, these outfit pairings will have you both feeling confident and ready for anything.
Classic Chic + Casual Cool
For a timeless and stylish look for your date night , why not mix classic and casual? A little black dress (LBD) for her paired with a sleek blazer or button-down shirt and dark jeans for him creates the perfect balance. The LBD is always a safe bet for an elegant, confident look, while the sharp but laid-back blazer and jeans combo for him exudes effortless cool.
Romantic Boho + Modern Edge
If you’re heading to a more relaxed date night, like a wine bar or casual dinner, try pairing a flowy, bohemian-inspired dress for her with leather boots or strappy sandals. For him, opt for a relaxed, modern look with a fitted denim jacket over a plain tee and slim-fit pants.
Sexy and Sophisticated
If you’re aiming for a night of high-end dining or an upscale event, an outfit that balances sexy with sophistication is the way to go. For her, think a silk slip dress in a rich jewel tone paired with heels and delicate jewelry. For him, a well-tailored suit or a dress shirt with a fitted blazer creates the perfect contrast.
Casual Cool + Playful Layers
For a more relaxed date, like a movie night, bowling, or a fun outing, opt for a cool graphic tee paired with denim jeans for him, and a trendy jumpsuit or casual romper for her.
Edgy Glam + Polished Sophistication
For a date that requires a bit of edge—think live music, a night club, or a cool rooftop bar—try pairing an edgy leather jacket with a sleek bodycon dress for her, and a black bomber jacket over a turtleneck sweater and slim jeans for him.
Cozy Casual + Effortless Chic
When you’re in the mood for a cozy night in or a casual stroll, pairing oversized sweaters or knit dresses with leggings or skinny jeans offers both comfort and style. For him, go for a cashmere sweater or a casual knit polo with your favorite pair of chinos or jeans.
Flirty and Feminine + Polished Masculine
If you want to go for a playful yet classy vibe, you can play hard on your feminine energy by rocking a flirty dress or skirt. For him, go for a blazer in a neutral tone styled on a tee.
Sporty and Chic
If you’re going for a sporting or casual activity such as golfing, a day in the park, or just a casual outdoor activity, consider sleek joggers or leggings paired with a crop top for her and a cool track jacket, zip-up hoodie, or bumper jacket for him.
Winter Cozy + Luxe Details
When it chilly outside, you may want to layer up and so so stylishly. Consider styling a faux fur coat or wool trench coat over a cashmere sweater for her and a peacoat or wool blazer over a turtleneck sweater for him.
Laid-Back Lounge + Stylish Comfort
If you’re considering staying indoors for your date night, you can match comfort with style in a matching loungewear, jogger set, with slip-on sneakers or house slippers.
