Need inspiration for date night outfits? These chic date looks are stylish, sassy, and your date will definitely love them too!
Dating can be stressful, but your date night outfits don’t need to be! Whether you’re going on a casual date or a fancy dinner, the perfect date night outfit is cute and comfortable enough so you can relax and enjoy yourself.
I’ve put together seven date night outfit ideas that I’ve worn out on different dates–all repeat looks in my book. Keep reading to find the perfect outfit for a first date, a Valentine’s Day dinner, or your weekly date night with your partner.
This post is all about date night outfits.
Best Date Night Outfits
1. Simple Date Night OUtfit: Basic LBD + Leather Jacket
I can’t think of anything more classic as a date night outfit than a little black dress. The simplicity of the dress makes a good background against a statement jacket and any fun accessories you add to the look. Pair your LBD with a leather jacket or a moto jacket and you have a look that can be styled year-round.
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For matching footwear, try combat boots for an edgy look, tall boots for a fall date night outfit, or strappy sandals for a summer date look. The footwear options are endless when styling with a black dress. And let’s not forget a classic black pump to add some feminine flair. Add a pop of color with a cute clutch or mini bag.
Shop The Style:
- Banana Republic Factory Vegan Leather Short Jacket (timeless + of-the-moment)
- Bernardo Edge City Moto Leather Jacket
- Good American Stretch Rib Knit Scoop Back Midi Dress
- Lululemon All Aligned Stretch Rib Midi Dress
- ATM Anthony Thomas Melino Stretch Pima Cotton Jersey Mini Dress
- John Elliott Gemini Rib LS Keyhole Midi Dress
- ba&sh Cimo Leather Boots
- Dolce Vita Rainier Boots
2. Winter Date Night Outfit: V-Neck Sweater + Matching Jeans + Tall Boots
Styling a duotone look is simple when your shoes are the pop of contrast. Tonal looks help create length and fluidity in the body while contrasting pieces add interest to a simple date outfit.
Style a v-neck sweater with a pair of your best-fitting jeans to create a sexy, but casual date night outfit. A wide v-neck may show some extra skin, which is flirty and fun, but still keeps things a bit cozy. Amp up the sass with a pair of tall boots that easily style over your jeans for a definite head-turner at a sports bar or a brewery.
I love to add a contrasting piece like the black boots to create an unexpected look for a winter date outfit. This is a style tip used for any casual chic look, something done well by Parisian women.
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Shop The Style:
- Quince 100% Organic Cotton Fisherman Sweater
- Fore V-neck Cropped Cardigan
- COS Rib Knit V-Neck Vest (chic sleeveless option for a spring outfit or layering)
- And Other Stories Slim Cut Jeans
- Madewell The ’90s Straight Jean
- Nisolo Vegan Noemi Belt
- Banana Republic Cinza Nubuck Leather Belt
- Topshop Tara Premium Leather Knee High Boots
- Staud Wally Boot
3. Casual Chic Date Outfit: Tank + Wide-Leg Trousers + Flats
I’m a huge fan of monochromatic and tonal dressing (in similar or matching colors). The obvious choice for a cute date night outfit is all black, which I’ve chosen to style.
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A simple tank, even a knit style, with a pair of relaxed trousers is the perfect go-to date outfit when you’re in a rush or you don’t want to look like you’ve tried too hard. It doesn’t get much simpler for summer date night outfit with a cute pair of ballet flats or sandals.
Style a simple date outfit like this with a pair of elevated flats as opposed to a cheap, basic pair. Footwear says a lot about a person, so it’s an important component of your outfit on a first date.
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Shop The Style:
- L’Agence Kaeli Top
- Banana Republic Sublime Silk Tank
- Amanda Uprichard Ariya Pant
- Massimo Dutti Ballet Flats With Gathering
- Kenneth Jay Lane Satin Gold Long Leaf Pierced Earrings
4. Date Night Dresses: Belted Mini Dress + Tall Boots
Mini dresses are the perfect choice for sexy date night outfits, but have you thought of changing it up with a stylish waist belt? Not only does a belt add a personal touch to a one-piece outfit, it also helps enhance the shape of your curves (and helps give you curves if you’re lacking).
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Tall boots are so flattering with mini dresses, whether they’re knee-high or over-the-knee boots. Add a pair of dark stockings to create more allure to your outfit and you’re set for a hot date!
Style with a medium or large clutch to add some contrast to the mini factor of the dress.
Shop The Style:
- Current Air Autumn Ruffled Mini Dress
- Misa Los Angeles Saffie Dress
- Tory Burch Tall Banana Boot
- Tory Burch Split Mignon Multi-Strap Heel (perfect spring or summer sandals)
- Calzedonia 20 Denier Back Seam Sheer Tights
- HautCuir Meera Wide Leather Belt
- The Bridget Mini Satchel by Melie Bianco
- Tory Burch Kira Velvet Mini Flap Bag
5. Sexy Date Night OUtfits: Sheer Top + Satin Pants
Lace is the ultimate sexy material for a date night outfit, as is its younger sister, mesh. You have the sultry, see-through factor you can choose to layer a cami or bra under depending on the look you’re going for.
Style a pair of slinky satin or silk pants to create a super, feel-good look that’s equally comfortable without being too dressy (although perfect for both the stylish restaurant and the nightclub after).
This date night look can be styled with any type of footwear for a year-round date, indoors or out. I love dressy jogger pants because they’re so comfortable for how cute they look.
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Shop The Style:
- Helsa Sheer Sleeveless Knit Draped Top (perfect for spring and summer)
- By Anthropologie Draped Mesh Tank
- Free People Lady Lux Layering Top
- Marcella NYC Eloise Sheer Turtleneck
- Reformation Olina Silk Pant
- NIC+ZOE Elevated Satin Tapered Leg Cargo Pants
- ba&sh Battista Belt
- SARTO by Franco Sarto Amaya Flexa Flat
- COS Leather Trimed Lace Ballet Flats
6. Fall Date Night OUtfits: Flirty Top + Belted Long Skirt + Boots
This may be my favorite outfit combination to wear on a date because it’s so versatile. Take any flirty top whether it’s a low-cut knit top, a sheer blouse, or a bodycon sleeveless turtleneck, and belt it with a slinky maxi skirt.
Add a heeled boot or shoe to give a little height and you have a super feminine date night look that works year-round with different tops.
If you’re attending a winter concert or a jazz concert for a date, a slinky skirt is a great option. This outfit is perfect for dancing in and ensures you won’t overheat. Opt for an open-toed boot in spring and summer.
Shop The Style:
- H&M One Shoulder Rib Knit Top (spring & summer outfit ready)
- H&M Rib Knit Sweater
- Reiss Dani Rib Tank
- J. Crew Collection Maxi Skirt in Lightweight Chiffon
- COS Asymmetric Pleated Midi Skirt
- ReddApple Starry Beaded Necklace
- Steve Madden Cashel Black Leather
7. Casual Date Night Outfit: Blazer + Band T-Shirt + Jeans
There’s not a going out outfit post that goes by without me mentioning a band t-shirt. But hey, I’m a huge fan of the style (especially when a personal touch is added, re: below). This date outfit look would totally work with a plain white t-shirt as well, so you do you!
But, if you go to a lot of concerts (or maybe you’re going on a concert date) this is a winning outfit. The blazer just takes the look to a different level, a mix of classy and casual, which never fails to please.
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Style with a pair of western boots or patterned boots, like I did, for a rock and roll aesthetic. You can also add a cute hat with this outfit if you’re going on an outdoor date or traipsing around the streets of Nashville.
Shop The Style:
- Camila Coelho Arielle Blazer
- Open Edit Relaxed Fit Blazer
- Liquid Blue Grateful Dead Carpet Ride T-Shirt
- Mother The Hustler High Rise Ankle Fray Jeans
- Reformation Margot High Rise Flare Jeans
- Reformation Otto Mini Western Boot
- Marc Fisher Elma Perforated Western Bootie
Which of these date night outfit ideas were your favorite? Comment below.
This post was all about date night outfits
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