9 Date Night Outfits That Look SO Stylish But Take Little Effort

Whether you love a casual dinner or an all-out affair, it’s fun to step up your game on date night. Spending quality time with a special someone, your loved one, or even someone you have a solid “like” for 😉 can call for a little extra something in the outfit department. But notice we didn’t say complicated. Date night looks don’t have to be fussy to be sexy, sophisticated, and “extra”! We wanted to share with you 9 stylish looks that are easy to throw together with minimal effort but still bring a little bit of va va voom for date night. These looks would also be amazing for girl’s night!

Once you have your outfit all picked out for date night, maybe you want to try something new in the makeup department too? This post has a few timeless and beautiful makeup looks that are easy to replicate.

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what to wear new years eveLeather + Lace outfit | Effortless Date Night Outfits

Effortless Date Night Outfits

1) Leather + Lace

What could be simpler than a blouse and pants? Really that’s what this outfit breaks down to! Erin is wearing a sexy and uber-sophisticated lace top by Jonathan Simkhai. It’s feminine and romantic but because it’s completely sheer it has some sex appeal too. You can either wear a black bra top or cami underneath depending on your comfort level. It has a satiny collar and cuffs which are such elegant details. Erin paired the top with a cool and edgy pair of faux leather pull-on (yes, pull-on!) pants by Commando. They have plenty of stretch in the tummy area, and a flattering center seam down the front that elongates the legs. The split hem is super on-trend, creates a flattering line and highlights her fabulous shoes. If you want to go with a more casual look, you can swap the faux leather pants for a pair of dark wash or black denim. Easy-peasy.

Effortless Date Night Outfits

2) Sweatshirt Dress + Booties

What if we told you this look is as cozy and comfy as your favorite pair of sweats? Yep! This faded black dress by Isabel Marant Etoile is made of a midweight French terry that is super soft and comfortable. It has dramatic puff shoulders and super flattering ruching around the tummy area. The length is pretty perfect on Erin at 5’4”. But if you are worried about it being too short, just add a pair of tights or black leggings underneath. Erin paired it with some western-inspired booties for an added touch of edge. This is definitely an effortless, cool-girl outfit that will turn heads…and again, so simple with just 2 pieces. After date night, you can also style this dress with sneakers and a leather jacket to get more wear out of the same piece.

Faux Leather Joggers + Statement Sweater

3) Faux Leather Joggers + Statement Sweater

This next look would be so chic for date night, but the sweater and joggers can also be styled a bunch of different ways this winter. These faux leather cargo joggers by Generation Love are both edgy and on-trend (and currently on sale!). They have a comfy elastic waistband, cinched cuffs, and cargo pockets on the sides. These look even more luxe in person and the fit is lovely. They are a tiny bit long on Erin but if you’re petite, you can always cinch the elastic cuff up your leg a bit. Erin paired the joggers with a pre-layered sweater by Cinq a Sept. What a statement-making sweater with the tie cuffs and flattering rounded hem. And no fuss whatsoever! On her feet, Erin’s wearing a pair of Michael Kors faux leather booties that she owns in both black and brown. They’re super sexy, unique, easy to style, and VERY comfy. The sock bootie silhouette means they’ll work with any pair of jeans, dresses, and skirts. To amp this look for date night add a red lip, a pair of sparkly earrings, and a black clutch.

Affordable Holiday TopsEffortless Date Night Outfits

4) Emerald Green Top + Jeans

If your idea of a chic date night look almost always includes denim, these 2 looks are for you! Emerald green is such a gorgeous color for most women. It just has such an opulent look about it. While both of these tops have very different cuts and fits, the beautiful green is the standout here. On the left, Erin is wearing a Farm Rio body-skimming top with a smocked mock-neck and sleeves. It has the prettiest pintuck and ruffle details and is very lightweight so you can layer it easily under a jacket or coat. On the right, Erin’s wearing an ASTR The Label top with a sweetheart neckline and flattering ruched bodice. It runs slightly small so if you are between sizes, we suggest sizing up. It’s also very cropped so you’ll want to style it with high-waisted bottoms.

Erin is wearing both tops with a flattering pair of straight-leg jeans by L’Agence. The dark wash makes them feel more elevated and the cut is SO slimming and classic. Grab your favorite booties or pumps and you are date night-ready.

Vegan Leather Blazer + Jeans | Effortless Date Night Outfits

5) Vegan Leather Blazer + Jeans

Now if you want edgy sexiness that inherently comes with leather and vegan leather AND the comfort of jeans, this next date night combo is another great option. This vegan leather Cinq a Sept blazer is SO luxe and beautiful. The dark brown color is even more rich and luxe in person. The fit of this blazer is incredibly flattering. It has a slight fit and flare silhouette that cinches the waist and creates the illusion of an hourglass shape. For date night you could wear a lacy cami underneath but then you could also wear this blazer with a white tee, tank, or button-down for lunch with the girls, or the office. This is one of those blazers you’ll wear for years and years to come.

Erin styled it with a pair of dark wash, high rise bootcut jeans by AG to keep the line long and lean. And, on her feet the same pair of Michael Kors booties mentioned in look #3 but this time in chocolate brown.

Winter Dresses for Women

6) Vegan Leather Dress + Booties

Sticking with both the vegan leather theme AND the easy theme, how gorgeous is this Cinq a Sept dress? It’s the same color and fabric as the blazer in the previous look. Everything about this dress is SO good…the long sleeves with bell cuffs, the flattering twist front detail and v-neckline, and the beautiful deep brown color. Erin is wearing it with some cool geometric dot-patterned tights and the same Michael Kors booties you’ve seen a few times now in this post. A one-and-done dress like this has ease, comfort, and the “wow” factor all rolled into one!

Ribbed Dress + Sexy Tall Boots

7) Ribbed Dress + Sexy Tall Boots

While black is such a great color for date night, some of you have shared that this sexy color can look a bit too harsh on your skin tone. So, these next 2 looks (along with the previous) are all rich chocolate brown options. This mixed-media Staud dress is one of those unexpected stunners. It has this corset-like fit at the bust, a thigh-high slit on the side, and is form fitting…I mean this dress is sexy! But in contrast, you get this soft and comfortable ribbed material for the bodice, and a cotton poplin collar and long sleeves. Such a unique combination that is both sexy and sophisticated.

Sexy Fitted Dress + Sexy Tall Boots | Effortless Date Night Outfits

8) Sexy Fitted Dress + Sexy Tall Boots

If you’re looking for something even sexier and dressier than the last look, this dress will do the trick! This Norma Kamali dress is super fitted but has strategic ruching that’s SO flattering. We love the drama of the asymmetrical hem. It’s pretty short on one side but the long sleeves, turtleneck, and length on the opposite side offset that so you don’t feel like you’re showing too much skin. Erin styled it with the same knee-high Schutz boots as the previous look to create another monochromatic and sleek outfit.

How To Wear A Sweater Dress With Ankle Boots

9) Sweater Dress + Booties

This next dress is incredibly comfortable and perfect for an easy date night look. It’s a black Steve Madden sweater dress that’s so good…and SO affordable (only $99!). The material is thick enough to hide lumps and bumps but not too thick. So if you run hot or are dealing with hot flashes, this dress still works. We love the one-shoulder neckline that’s very flattering on most body shapes. It has a roomier fit in the waist, which will help hide any tummy concerns you may have. But the bottom half is fitted and flattering. It’s also a great length! Erin added a wide waist-cinching black belt by Dior which we are unfortunately unable to link, but we found a similar one and included it below.

Erin is wearing her go-to Stuart Weitzman sock booties that she’s owned for YEARS and wears with pretty much everything. Because the ankle is fitted to the leg, you can wear these booties with any jean styles, dresses, skirts, pants, etc. And…they definitely turn up the sexy too.

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We just had to share this next look because it comes with a very sweet story! Now, this is certainly a dialed-up date night look. Is it easy? Yes, it sure is even though the sequins might be giving it “fussy” vibes, it’s just another one-and-done piece. Anytime you can just throw on a dress and booties and look this incredible…why wouldn’t you? Erin took images in this beautiful Maje dress as a great New Year’s Eve option…you can see all the details in this post. Then, her husband Chris saw the photos and told Erin that he wanted to take her out in THAT dress! So, why not?

It has a gathered waist and fold-over flounce skirt that are SO flattering. The long sleeves and boatneck contrast the amount of skin you’re showing with the shorter length and sexy back. The completely open back has delicate black straps that are very pretty. You can either wear nippies with this dress or no bra. It runs true to size and Erin is wearing a 1 (that fits like a 2-4). To dress this look down a bit, just opt for simple earrings and a black clutch.

What is the very BEST date you’ve even been on? Where did you go or what did you do? We’d love to hear about it in the comments!

2024 is just around the corner. If you haven’t yet signed up to be a subscriber now would be a great time! We have so many exciting new resources to share with you in the coming year and we’d love you to be a part of our Busbee Style community! You can sign up here.

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