12 Date Night Outfits To Make Getting Dressed for Date Night Easier!

Date Night Outfits for Every Season

Do you struggle to put outfits together that you love for date night?? I know I do sometimes. I want to look sophisticated and yet add a dash of sexy while still remaining comfortable. The great news is… date night outfits do not have to be difficult or over-the-top sexy. You can wear jeans and more comfortable clothes…and make them date night appropriate by simply making a few style tweaks. Below, I’m sharing 12 chic date night outfits for women over 40 that are easy to recreate! Yes, 12! (We are over-achieving ;)) Each outfit can range from casual to dressy, depending on your date night plans. The 12 looks are divided into seasons and strategically include many wardrobe basics that can be worn year-round.

Need more date night out inspiration? I’m sharing a few older posts below to give you even more ideas…

What Should You Not Wear on a First Date – 8 Pro Tips
5 Easy Date Night Outfits That Require Little to No Effort
Style Guide: Date Night Outfits for Every Season
What to Wear When You Haven’t Dated in Years

Date Night Outfit Details

Before we dive into the 12 date night outfits…I want to talk about a few details to look for or include when putting together your date night outfit. Your date night outfit can be as simple as a cute top and jeans. But the details of the top or jeans are where you can really turn it up a notch. I’ll discuss the details more in each look below but here are a few more examples of details that will add a little sexy to your date night looks…

• Plunging necklines
• Open-back tops, sweaters, and dresses
• Off the shoulder tops, sweaters, and dresses
• Split hemlines on dresses, skirts, jeans, and pants
• Cutouts
• Modern details like puff shoulders, sheer panels, flared sleeves, on-trend denim, distressing, gold button details, feathers, ruffles, etc.
• Fabrics like silk, satin, lace, leather (faux or vegan), and velvet
• Shorter hemlines (if you like your legs)
• Fitted silhouettes (if you’re feeling good about your body)
• Body skimming tops and sweaters
• Anything that makes you feel confident and sexy!

Winter Date Night Outfits

Casual Date Night Outfit for Winter

First up is a casual date night outfit that you can wear during winter. This is the outfit you’ll wear if you’re in a hurry and running out the door to your favorite local dinner spot with your significant other. These dark wash AG jeans are a great basic you can wear year-round, and the fit is SO good…I have them in a different wash and love them. Next, pick a casual top or sweater with a modern detail (refer to the list above for examples of modern details!). This Good American sweater bodysuit with a chic cutout on the chest is a perfect example. It shows just the right amount of skin! Then throw on some edgy combat boots to keep it casual. You could also swap the combat boots for your favorite black booties you already have in your closet. Add a black coat, some jewelry, grab your handbag, and you’re ready to go!

Note: You can make tweaks to any of these outfits to make them your own. Just because you don’t have these exact pieces, doesn’t mean you can’t recreate this look.  Get creative and try on variations of these outfits that make YOU feel good!

Elevated Date Night Outfit for Winter

This date night outfit is a little more elevated than the previous look. Instead of classic jeans, try some cool leather pants like this pair by Good American. To keep the look streamlined, go with a black top and black booties. This top has a sexy v-neckline and the booties have an on-trend block heel that also makes them easy to walk in. This look would be even sexier with a pair of black stiletto heel booties too! For your third layer, you can wear your classic black coat or opt for a statement coat like this one by Avec Les Filles. Finish off the look with your favorite modern bag and jewelry. This Cult Gaia necklace is beautiful and really makes a statement!

Dressy Date Night Outfit for Winter

If you’ve been a long-time subscriber, you know how much I love wearing light neutrals…especially during the winter. This dressy date night look would be beautiful during the winter. I love the cable knit detailed fabric on this Line & Dot sweater dress. It’s super body-skimming and has slits on the sides, which adds a little sexiness and frames a fabulous pair of shoes. Style it with a pair of brown knee-high boots, a gorgeous camel coat, and some statement jewelry. I love the white and brown color combo on this Staud bag that’s so subtle and makes it super versatile…you can use it in spring and summer too!

If you’re wondering how to wear dresses with boots, make sure you check out this post.

Spring Date Night Outfits

Casual Date Night Outfit for Spring

Next up are some fun spring date night outfits! For this casual look, I took a commonly worn piece among busy women (that’s you!) during the spring…a tank dress! This tank dress by Enza Costa is super flattering, has a beautiful neckline, and is a great length. You may be looking at the graphic and thinking…”I can wear sneakers on date night?!” You sure can! As long as wherever you’re going isn’t too dressy, you can get away with sneakers because they’re SO on-trend. This doesn’t mean you should wear your running shoes to dinner…choose a pair of sneakers that are a little more elevated. Then, throw on a chic third layer like this puff shoulder Retrofête jacket. It doesn’t have to be this exact denim jacket or even a denim jacket at all! You could wear a blazer, cargo jacket, or trench coat too.

Elevated Date Night Outfit for Spring

If you prefer to wear jeans, this outfit is for you! Light-wash denim is a must-have for spring, and I love these straight-leg Levi jeans (under $100!). Pair them with an elevated top like this one by Endless Rose…it has the sexy off-the-shoulder portrait neckline and gorgeous gold buttons that make it look so luxe (seriously, you won’t believe the price). You can wear the jeans, top, and sandals on their own or throw on a third layer like this suede Blank NYC jacket for extra warmth and a touch of edge.

Dressy Date Night Outfit for Spring

This dressy date night outfit is for all of my fashionistas and is a bit of a wildcard but it’s SO fun. If you don’t like to wear white, you can get the same look by wearing suit separates in black, camel, navy, pink…or whatever color you prefer! But I personally love white. This Line & Dot blazer and pants set is so chic and would be so cool if you have a fancy date night coming up. I love the feathers on the sleeves of the blazer and the wide-leg pant silhouette is very flattering. I’d pair it with a simple cropped cami underneath but you could wear a white shell or blouse if that’s more comfortable for you. Wear white or skin-colored heels to make the legs look long and lean. Then finish it off with bold jewelry and a fabulous clutch.

Summer Date Night Outfits

Casual Date Night Outfit for Summer

Summer date night outfits can be difficult. You want to look chic, sophisticated, and sexy without showing too much skin. But it can be SO hot depending on where you live. Here’s a foolproof formula…

If you’re wearing a sleeveless top, keep your legs covered. If you’re exposing your legs, keep your arms covered. I always suggest adding a third layer (even if you just drape it over your shoulders), but I know that’s not possible for everyone…I’m talking to you ladies in Texas and Florida 😉

For a casual summer look, I’d go with something like this fun pink blouse with pretty pleated flutter sleeves. If you don’t like pink, swap it with a different pop of color. I’d go with something pretty and bright…whatever makes you feel happy and confident. Then wear your favorite pair of white jeans. I love these Mother jeans because they’re super flattering, not see-through, and work with pretty much any style of shoe. Throw on your favorite jewelry, espadrilles, and a straw or rattan bag and you’re ready to go!

Elevated Date Night Outfit for Summer

For a more elevated summer outfit, consider styling your favorite summer shorts for date night! These leather Good American shorts have an elastic waistband and flattering A-line fit that will actually make your legs look slimmer. Since most of us are usually a little more casual during the summer, I wanted to keep this “elevated” look still pretty casual. So I chose a Nation LTD tee with ruffled details to pair with the shorts. Next, throw a blazer over your shoulder (bonus points if it’s an on-trend oversized blazer), add some jewelry, and a handbag…and you’re ready for date night! I chose some flat Sam Edelman sandals for this look, but you could swap them for some cool strappy heels if you wanted to take this look up a notch.

I shared 8 tips on how to find the most flattering shorts over 40 in this post in case you’re interested.

Dressy Date Night Outfit for Summer

For a dressy summer date night, wear a skirt! This silky Anine Bing skirt is super sexy but silk can be tricky during the summer. If it makes you more comfortable, recreate this look with a black cotton skirt instead. Pair it with a fitted tank like this one by A.L.C. that has elevated details like the thicker straps and sweetheart neckline. If you’re not comfortable with your arms showing, drape a double-breasted blazer over your shoulders. This Lioness blazer is SO good, under $100, and a great basic! Elevate the look with strappy heels, a modern handbag, and some fabulous gold jewelry.

Fall Date Night Outfits

Casual Date Night Outfit for Fall

Keep your fall date night outfit simple with a pair of jeans and a printed blouse. These Agolde jeans have a cool criss-cross waist that’s super flattering. I have them in a lighter wash and love them. The Ulla Johnson blouse is beautiful and this brand is known for its gorgeous prints. But you can swap it for a different printed blouse if you prefer. Add a fun third layer like the Blank NYC faux fur jacket…I’ve had it for a few years and LOVE the gorgeous brown color, luxe feel of the fabric, and beautiful fit. Oh, and it’s under $100! Finish off the look with some jewelry, a handbag, and some brown mules, booties, loafers, or whatever you prefer.

Elevated Date Night Outfit for Fall

I love the modern, sexy look of this sheer mock neck top by Generation Love. Mesh and sheer panels are one of those details I mentioned at the beginning of the post that add a little extra sexiness to an outfit. For this elevated fall look I wanted to go with an all-black outfit so I chose a pair of black Mother jeans that are super flattering, a sexy faux leather blazer by Good American, and some modern cone heel booties by Isabel Marant. Add a pop with some bold gold and/or silver jewelry and you’re date night ready!

Dressy Date Night Outfit for Fall

Because I gave you a super dressy date night outfit for spring…I wanted to do the same for fall. But this look could be worn for a fancy date in any season, really! This Good American jumpsuit has a sexy plunging neckline, is fitted through the waist, and has flattering wide legs to create that hourglass figure. To add some coverage, I’d throw on a third layer like this blazer. I love the subtle crystal details on the collar, lapels, and down the back of the arms that elevate the blazer even more. Add some black pumps, statement earrings, and a classic black clutch and you’re ready!

Which of these date night outfits is your favorite? Were you able to get some outfit inspo for your next date? Please share in the comments below!

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