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August–what!? I feel like summer just started. 😭 But by now, you’re probably sick of the same old “summer date outfit” rotation now that we’ve been in the swing of hot weather for the last couple of months. So if you’re looking for some outfits to shake things up for your next summer date night…you’re in the right place!
As you probably know by now, I’m a big fan of “outfit formulas” that I’ve gravitated toward over and over throughout the years. Below, I’m rounding up all my favorite summer date night outfits that never go out of style, so if you’re in a style rut, you can always come back here and hopefully get some new ideas on how to recreate the same looks in your own wardrobe! (Don’t worry, you’ll find links below each look if you are hoping to do some shopping, too!)
27 Summer date night outfits
Black Puff Sleeve Poplin Top (TTS, wearing small) also love this one / Abercombie White Jeans (TTS, wearing 26) / Nude Heels (TTS)
BLACK AND WHITE: PUFF SLEEVE POPLIN TOP AND WHITE JEANS
This is a really simple date night outfit that works for any occasion! That’s the best part about white jeans—are they formal? Are they casual? It depends on how you style them! For this look, I went with a black poplin top with a statement sleeve and nude block heels, making it semi-formal. To dress it up even more, though, you could add a few pieces of simple gold jewelry. Black and white never goes out of style!
Abercrombie Ultra High Rise Linen Tailored Shorts // Abercrombie Linen Blend Foldover Top // Abercrombie Bubble Strap Poplin Top
HIGH-RISE LINEN SHORTS AND A CROP TOP
Here’s a simple but elevated look for a hot outdoor summer date. (Hot as in weather, but can also be applied to your date 😉) To wear this outfit, pair breezy white linen shorts with a print crop top. For shoes, you could go with sandals, heels, or even white sneakers. The top’s elegant style and print make it pretty versatile! (I love the neckline!)
Madewell Gingham Lightspin Dress // Madewell Court Sneakers (TTS)
CUTE CASUAL: GINGHAM SHIFT DRESS AND WHITE SNEAKERS
This dress–a swingy silhouette–is super cute and easy to style. Add white sneakers and you’re basically done! This is the perfect thing to wear on a casual daytime date, to the farmers market or an outdoor concert. You could swap the sneakers for heels too if you want something a bit more dressed up, but still want “girl next door” vibes.
Amazon Maxi Dress (reviewed here–go with your smaller size if in between unless you need room in the chest!) // Amazon Nude Sandals (TTS)
BLACK MAXI, WHITE DENIM JACKET, AND NUDE SANDALS
Black maxi dresses are one of the most versatile pieces in your closet. Everyone needs an LBD—a long black dress, that is. To style it for a date, try adding a belt, structured jacket, and heeled sandals. You could go with any color for these accessories too! Make it vibrant and exciting with color and print, or keep it elegant and understated with neutrals—whatever you’re feeling!
Abercrombie Satin Scoopneck Tank // Abercrombie Linen Trousers // Madewell T-Strap Sandals
BLACK ON BLACK: BLACK TANK AND TROUSERS SET
A monochrome outfit is an easy go-to for an elevated date night look. For this outfit, I simply paired a black tank with black linen trousers and accessorized with neutrals. You could do this same thing with any color! (A great vacation outfit, too!)
Similar dress here and here and here // Tretorn sneakers (and other fav white sneakers here!)
FLORAL DRESS AND WHITE SNEAKERS
A floral dress and white sneakers is always a safe bet. It’s fun and flirty while still being sophisticated and feminine. More tips on wearing sneakers with dresses HERE!
Free people bodysuit // Similar white denim mini skirt // Tretorn sneakers (and other fav white sneakers here!)
BLACK BODYSUIT AND WHITE MINI SKIRT
A bodysuit, skirt, and sneaker combo is the perfect “sexy but not trying too hard” combo that I think is perfect especially for a more casual first date. Again with that classic black and white color combo–but I added a little pop to the outfit with a hair scarf. They’re so cute, add a lot of style to your outfit and best of all–keep your hair out of your face on hot days!
Similar Tee here and here and here // Similar white denim mini skirt // Similar Amazon Scarf
STRIPED TEE AND WHITE DENIM MINI SKIRT
I love a striped shirt. It’s easy to wear, elevated, and versatile! Don’t only think of it as a daytime staple–you can dress it up with a denim mini-skirt for a comfy casual summer date night outfit. Then, try bringing it together with–you guessed it–a hair scarf, and sunglasses. I wore this outfit to dinner in Florence.
Hill House Ellie Nap Dress (this color/pattern is a few years old but they have so many cute colorways!)
NEVER NOT WEARING A NAP DRESS:
This Hill House Ellie Nap Dress is one of the only things I want to wear when it’s super hot outside! I love wearing it on a picnic date, or just a casual walk around the neighborhood. It’s feminine without trying too hard. Pair it with simple nude block heels, espadrilles, sandals or of course, sneakers.
Similar linen jumpsuit (Everlane makes a cute one too!) / Identical sandals (they’re supportive too!!) / Similar bag
CHIC JUMPSUIT AND FLAT SANDALS
Jumpsuits are another closet piece that are easy to style–and you likely already have one in your wardrobe! Try pairing one with neutral accessories like heeled sandals and a tan belt bag. To make it even more chic, pull your hair into a low bun and add some chic sunnies for riviera vibes (even if you’re not on the riviera!)
Similar dress here and here and here // Tretorn sneakers (and other fav white sneakers here!)
DENIM MINI DRESS AND WHITE SNEAKERS
Denim dresses are sexy and chic—perfect for a date night! Try wearing it with white sneakers, sunglasses, and a little red lipstick. (ILIA colorblock lipstick is one of my favorites currently!)
Amazon maxi dress // Favorite Amazon Strappy Heels
PUFF SLEEVE MAXI DRESS WITH WHITE HEELS
Here’s a maxi dress look with a little color. Go with a bold color with puff sleeves for a date night look OR one perfect for a summer wedding, nice dinner, or really any other event. With a color these exciting, neutral accessories should do it—but feel free to get adventurous if that’s your style!
Similar dress here and here and here, Hair Scarf, and Ray Ban Round Sunnies // Tretorn sneakers (and other fav white sneakers here!)
LITTLE RED DRESS AND WHITE SNEAKERS
We talked about LBD, but what about LRD? I personally love a little red dress. I love short mini shift dresses because they are cute to pair with white sneakers–making them a practical option that is perfect for a summer concert or bopping around the city–any date where you’ll be doing a lot of walking!
Amazon maxi, Nisolo Huarache Sandals (one of my favorite sandals to travel with!)
FLORAL MAXI DRESS AND WOVEN ACCESSORIES
I love wearing this maxi everywhere from a weeknight dinner date at home, to dinner on vacation. (I wore it a ton in Spain!) To style this floral date night look, try rattan or woven accessories.
ABLE Smocked Blouse // ABLE Chelsie Jeans // ABLE Tamara Heels (all reviewed here!)
SMOCKED WHITE TOP AND JEANS
Here’s another simple date night look you can probably assemble from pieces you already have in your closet! A smocked white top and jeans are classic and chic. Try it with heels and dainty gold jewelry to make it date ready!
Madewell Perfect Vintage Wide Leg Crop // Bailey Jacket (reviewed here–get a 15% off discount with JESSKEYS15) // Similar Red Top // All Star High Tops
WIDE-LEG WHITE PANTS, CROP TOP, AND DENIM JACKET
This date night outfit is perfect for summer nights because it’s layered and ready for quick weather changes. (In the Midwest, we have to be prepared for anything!) Wide-leg white jeans and a denim jacket are a great combo, but a bright-colored crop top really adds some visual interest! I went with a reddish-orange top, but you could do any color.
Similar Overalls (also love the Free People version!) // Similar Top here and here and here //All-Star High Tops
PUFF SLEEVE TOP AND SHORTALLS
I think overalls make the perfect date look. This is a fun outfit that could be at home anywhere from a dive bar to a food hall to a festival to cocktails in the West Loop. It’s a little tomboy chic, has lots of personality but not trying too hard. love the contrast between the structured overalls and the voluminous sleeves of the top!
Faherty Dress // Rothy’s Round-Toe Flats (reviewed here!)
STRIPED DRESS AND BOLD FLATS
A cute striped swing dress is a great thing to wear for any occasion! I like to make stripes pop with red shoes and lipstick. This is a date night outfit combo I wear often when I’m traveling, as we’re typically walking a lot of miles but I want to look feminine and chic at the same time!
Similar pink mini dress // Loeffler Randall Gold Sandals Low Heel – High Heel
MAGENTA MINI DRESS AND BOW HEELS
Here’s a more formal option! I like that this is still a mini dress in a youthful summer color, but it also has long sleeves and a sophisticated cut that make it more formal. I recommend bow heels with it because then you still have the fun flair but with another elevating piece! You can do a lot with this look and it’s cute for cocktails or even something like a rehearsal dinner!
Similar Top here and here and here // AGolde Parker Shorts Regular – Long // Similar Sandals
DENIM SHORTS AND WHITE BLOUSE
For a casual date outfit, try a short sleeve white top and denim shorts. This outfit uses the juxtaposition trick, with the rough, raw hem shorts and the more refined shirt! The accessories play by this rule too with casual sandals and a refined purse. If you struggle with styling stuff, this trick is always good to use!
Similar Jumpsuit here and here and here and here // Amazon Heels
BLACK JUMPSUIT AND NUDE HEELS
I love black jumpsuits for date nights and even weddings. (Yes! Weddings. Check out my post about it HERE.) To take it from casual summer wear to summer date night, pair it with nude heels, a denim jacket, and sunglasses!
Rent the Runway Romper // Similar Boots
BOLD PATTERNED ROMPER AND KNEE-HIGH BOOTS
If you haven’t heard of Rent the Runway, I highly recommend it! You can try out designer clothes without committing to the price tag. I got this romper from there, and it’s the perfect bold outfit for summer! You could pair this with knee-high boots, heels, or even high-top sneakers. I think this romper is Neal’s favorite thing I’ve worn all summer (and mine too!) 😂
Quince shirt dress (TTS, wearing small–comes in tons of colors!) // Amazon Strappy Sandals // Sezane Artemis belt // ABLE Maha leather jacket (use JESSKEYS15 for 15% off) but I also love Quince’s Moto Jacket! (Both are TTS and I like to size up to medium for both for a bit of extra room).
BELTED SHIRT DRESS AND WHITE HEELS
This shirt dress is one of my favorite pieces in my closet. I styled it several ways in this post if you like this look. For a simple date night edition of this shirt dress, try belting it, adding block heels, and rocking a moto jacket!
Jeans // Cami (budget-friendly version here) // Structured Jacket // Cap Toe Heels
RAW HEM JEANS AND BLACK STRUCTURED JACKET
Here’s another simple date night ensemble! I used that trusty juxtaposition trick and combined raw hem jeans and a cami, with a structured jacket and my fave cap-toe heels. You could wear this to a coffee date, a brunch date, or even a casual dinner date!
RUFFLE SLEEVE PRINT DRESS AND NEUTRAL ACCESSORIES
This ruffle sleeve dress is perfect for a summer date and can easily be dressed up or down depending on where you’re going! I’m thinking of date night while on vacation! Sexy but boho and ethereal–I love the ruffle sleeves and print, the deep V neckline, and you can easily accessorize it with simple neutral pieces and your fave shades.
Rent the Runway Top // Abercrombie Linen Shorts
CROP TOP AND WHITE LINEN SHORTS
Here’s another piece I snagged from Rent the Runway! This ¾ length sleeve sweetheart crop top I could wear all summer long. It’s so cute and it’s perfect for hot days. I wore it with linen shorts, but you could easily do denim or even a high-waisted mini-skirt.
This dress is a few years old, but this Faherty dress is similar and I love the pattern and look of this similar dress too! // Loeffler Randall Bow Heels (I love the Emilia (low heel) and Penny (high heel) versions the most!)
STRIPED SHIFT DRESS AND BOW HEELS
How about one last-shift dress? This one has vertical and horizontal stripes and comes in a fun summery color. I paired it with statement earrings and bow heels to take the more casual dress from lunch date to dinner date!
Summer date nights are the perfect style opportunity!
I hope these date night outfits helped you curate the perfect looks for all your summer plans! Make sure to check out the style section of my blog for more style inspo. (Or, if you’re in the southern hemisphere, perhaps my winter date night finds would be a better post for you!?)
