Chic Date Night Dresses for Women Over 50 for Every Occasion

When an opportunity to go out comes up, the first thing I always think is “What am I going to wear?” Nothing can take the wind out of my sails more than not feeling like I’m looking my best when having a date night with my husband or a night out with my girlfriends. I can only really speak for myself (and believe others may feel this way too), but the opportunity to get dressed up doesn’t come around too often these days. So I always want to take advantage of the chance and pull out all the stops. With Valentine’s Day quickly approaching, let’s explore some date night dresses for women over 50 that you can go to when the time comes to step out.

Date Night Dresses for Women Over 50

cream silk Date Night Dresses for Women Over 50 fountainof30

Date Night Cocktail Dresses

A cocktail dress would likely be my first choice if I’m heading out for dinner and drinks or even to the theater. I’ve become partial to satin dresses because they work really well with many silhouettes and the high-shine fabric always elevates the look. A simple option like this Zara ruched waist midi dress would be one that I would reach for over and over again. The overall cut as well as the ruched waistline offers a forgiving fit that will keep you comfortable but still feel sexy.


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asos Fallen Shoulder Bodycon Midi Dress fountainof30

Another satin option is this bodycon midi dress from ASOS. I covet the tucking details on the shoulder, which adds some beautiful dimension and depth to this dress.

Good American Exec Velvet Blazer Mini Dress fountainof30

Now, if you are in the mood for something a little unexpected, you can try this velvet blazer dress. The bright color and rich texture are playful and unique. I also love the length, which is perfect if you are one that likes to show a little leg (and if not, this pairs well with tights!) Add a pair of pumps and some bold metallic earrings to this dress and you’re ready for your date night out.

green Banana Republic Aurelia Crepe & Satin Maxi Dress fountainof30

Date Night Maxi Dresses

A maxi dress is also a really good option if you are looking for a comfortable and free-flowing vibe. I think choosing a maxi dress for a girl’s night out is a great option. When I get together with my girls, the food and drinks are always flowing, and I don’t want to worry about feeling bound in my outfit! I found two beautiful options from Banana Republic that are more upscale than others I’ve seen in the stores. This short sleeve crepe and satin option would look lovely paired with some leather Chelsea boots and moto jacket.

Banana Republic printed Ana Pleated Maxi Dress fountainof30

Or, if prints and patterns are your jam, you can try this pleated maxi dress. It would work with a chunky knit cardigan and a pair of ballet flats.

casual blue date night dress fountainof30

Casual Date Night Dresses

Not all dresses for date night need to be sleek and sexy. Sometimes a casual date is exactly what we need. You don’t always have to get glam. Some of my favorite date night activities include going to a comedy club or a concert; and I don’t want to wear a cocktail dress for that! Something low-key like this utility shirt dress is perfect for a casual evening out. You can throw on an oversized shacket and a pair of leather boots or even athletic shoes will work with this dress.

The Thea Twofer Sweater Dress fountainof30

You can also go casual with this Twofer Sweater Dress. I came across this one from Anthropologie and fell in love. This is one I would definitely wear on a date night. I’d pair it with some suede boots, a classic camel coat and a warm, plushy scarf. There is something about this dress that is casual but still has a high-end, slightly luxurious feel to it. I think it’s the mixing of the knit fabric top and silky skirt that results in a really beautiful harmony of fabrics.

Date Night Dresses Expert Style Tips

Lean into it. We all have that one fashion element that makes us feel special – a certain silhouette, color, fabric, etc. Find a piece with that feature and don’t be afraid to flaunt it. Having a night out is all about feeling sexy and uninhibited.

Have a good rotation. I don’t want to encourage over-consumption here, but there is nothing more satisfying to than cutting the tags off of a new dress when I’m about to hit the town. Have a couple of pieces ready to go when the time comes. Most of us fashion-lovers don’t love the idea of wearing the same couple of dresses every time a special occasion comes along.

Try to re-purpose. When looking for a date night dress, look for a couple of pieces that you can repurpose for other occasions. The maxi dresses that I highlight above can be worn in the office if you dress them down a bit, or throw a blazer or denim jacket over them. If you want to have multiple options available, you may as well find multiple ways to wear them!

Shop Date Night Dresses Here

Pictured above from left to right:

ZARA Ruched Waist Satin Effect Midi Dress, 69.90

ASOS DESIGN Fallen Shoulder Manipulated Tuck Bodycon Midi Dress, now $55.80

Good American Exec Velvet Blazer Mini Dress, $199

Banana Republic Aurelia Crepe & Satin Maxi Dress, $180

Banana Republic Ana Pleated Maxi Dress, $199.99

Utility Short Sleeve Zip Front Shirtdress, $75

The Thea Twofer Sweater Dress, $180

Do you have a favorite date night dress? Would you wear any of the ones I presented here?

–Carmen Turner

You may also like to read more of Carmen’s fashion posts like Cozy Casual Fashion: Where Comfort Meets Style for Women Over 50 and What To Wear To A Winter Wedding for Women Over 50.

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