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Six Top Date Night Outfits for Women over 40, 50, 60+

Women over 40 can achieve elegant date night looks by considering outfit questions and versatile pieces. A little black dress with appropriate footwear suits formal dinner dates, while office attire can transition with added glamour. Feminine dresses and jumpsuits offer figure-flattering options, and casual chic looks complement relaxed yet romantic outings like nature walks.

Date night outfits for women over 40 shouldn’t be tacky, plain, or boring.

As we mature, our fashion style changes and evolves, reflecting our journey through life, our refined tastes, and our changed budget. I used to be obsessed with mini skirts and high heels back in my twenties. Now, I prefer something that showcases sophistication and timeless elegance, while ensuring I feel comfortable throughout the evening.

Putting together the perfect date outfit comes down to asking your significant other the following questions: 

  1. Should I dress casually, or would something more formal be fitting?
  2. Is the venue indoors or outdoors?
  3. How fancy is the location?
  4. Is there a specific dress code I need to follow?
  5. What will the weather be like?
  6. Does it involve a low or high amount of walking?

Once you have your answers, you will have some direction.

I will share some of my favorite pieces to put together!

1. LBD – Little Black Dress

Every lady needs to have a little black dress in her closet.

It is a timeless and chic item for so many events. I like to advise short sleeved options or even sleeveless, since you can always layer or opt for no layers, this makes the dress very versatile.

Next, consider the fabric you choose: a linen is always going to be more casual, while a silk or satin gives off a dressier vibe.

This dress is perfect for your next date, whether it’s a romantic dinner or a night out on the town.

If the plan is dinner and the date is more formal, pair your dress with strappy sandals or some stylish pumps with a pop of color! I always opt for comfy wearable shoes no matter what throughout the night.

If you are aiming for a romantic brunch on the coast or wine tasting in the hills then opt for a stylish flat or a sophisticated sandal where you don’t need to worry about a heel and the terrain.

2. After-Hours Chic

If your date is right after working hours, I suggest making your office attire work!

You can wear a structured blazer with sleek trousers or a sophisticated pencil skirt for a contemporary yet timeless ensemble. Even if you had a busy day and important meetings, spicing up your outfit just a bit right after 5 PM is doable.

Wearing a silk or satin top for an added touch of opulence, or a button down blouse, with an extra button undone after 5pm and pair with your favorite perfume. Perfecto!

Switch out your work shoes for something more stylish, like heels, dressy ankle boots or booties, to add a touch of glamor.

This type of outfit will work well for a dinner date at night, art galleries, and museums, as well as wineries, or a show!

3. Feminine Dress

Embrace the versatility and femininity

Go for an off the shoulder dress for an effortlessly chic date night look or a casual stroll through your favorite little town.

Or opt for a wrap style that cinches at the waist and flatters your figure while enhancing your curves. A wrap dress is a common go-to for me personally during the spring season. It is flowy, comfortable, and super easy to dress up or down.

Then you can pair your pretty feminine dress with either sandals, flats, heels, boots – you name it!

Depending on where you are going, the shoes you pair with this dress will take you there!

So whether you are out for a drink or a cup of coffee these dresses will allow you to feel confident, pretty, and stylish all day long. They are sweet and sexy without being too over the top.

Casual date night outfits over 40 can look posh without being too much.

4. Jumpsuit

The right jumpsuit can boost your confidence and make you stand out at any event or get together.

Look for a well-tailored silhouette with a flattering neckline and tailored trousers for a sleek, elongated look. In case your jumpsuit is too long, I recommend getting it tailored.

You can wear your jumpsuit formally or casually, depending on where you’re going out on a date. A jumpsuit is a good option if it will be windy so you don’t have the troubles of the wind trying to give you a wardrobe malfunction.

It still gives you the one and done look, which can often be elevating and oh so easy too!

So, if it is a casual date? Maybe out to a bar, for some pool or a game?

I’d recommend flat shoes for ultimate comfort and a denim jacket as a third layer.

For drinks and a show pair with your favorite heels and clutch! Classic and versatile. 

5. Casual Chic 

Strike the perfect balance between comfort and style

Elevated basics are a great GO TO for a more relaxed yet chic look.

Casual chic doesn’t necessarily mean you didn’t put in effort making your look work.

You can pair lightweight cashmere top with some linen trousers for a monochromatic look. Or choose stylish pumps for a sophisticated yet effortless ensemble.

Maybe pair it with your favorite denim jeans and throw on some hoop earrings.

Casual chic often means you’re headed to the cinema, theater, or something relaxed, yet romantic, so have fun with this one!

6. Walking in Nature

Some of the best dates can happen in a park.

You’re surrounded by nature and animals, the sun is shining and you’re also getting a subtle tan (sounds perfect for homebodies)!

If you’re going for a picnic, a walk in the park, or if you plan on sitting on a bench and enjoying the scenery, make sure you’re comfortable.

White comfy sneakers or some flat strappy sandals and a white T-shirt that’s tucked into your jeans will look lovely. 

PS: Don’t forget your sunglasses and a sunhat outside! SUN HAT CARE VIDEO

I recommend you embrace your style and enjoy your unique approach to fashion.

You can make an impression and have a memorable date as long as you pair the right colors and rock them confidently.

So cheers to you, timeless elegance and unforgettable moments!

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