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ClassyTrendy · September 22, 2024

Here’s how to dress up for date night for women over 50

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Got a date night coming up? Part of the fun is to dress up and look stylish. Whether you are going to a casual place or upscale venue, we have 25 best outfit ideas for women over 50 that you must try!

Table of Contents

  • Leopard Skirt
  • Flowy Silk Blouse
  • The Ruffled Skirt
  • The Pencil Skirt
  • Faux Leather Leggings
  • The Leather Skirt
  • Sheath Dress
  • Lace Dress
  • The Pleated Skirt
  • Fit and Flare Dress
  • The Slitted Dress
  • Satin blazer
  • Wrap Dress
  • The Slited Skirt
  • Lace Top
  • Edgy Leather Coat/Jacket
  • Belted Shirt Dress
  • Denim Skirt
  • Velvet Pants
  • Metallic Dress
  • LBD
  • V-Neck Jumpsuit
  • The Flared Skirt
  • Plunging Ruched Dress

Leopard Skirt

Chic Outfits for a Night Out Over 40-Leopard Skirt

Try indulging in the bold and sophisticated allure of the leopard skirt for your next date. Its salient print brings an undeniable dash of glamor, whereas its flattering silhouette effortlessly enhances your appealing figure. 

As a woman over 50, you’ll love the timeless attraction and the confidence this skirt instills. Match it with a brown blazer and a V-neck white top for a chic and elegant demeanor that’s sure to impress. 

Flowy Silk Blouse

A flowy silk blouse is a type of women’s top made from lightweight, sheer fabric with a soft, flowing texture. They are versatile wardrobe essentials and are often worn for semi-formal to formal events such as weddings, dinners, and cocktail parties. 

For women over 50, this can be a great choice for your top. Silk blouses have an elegant, dressy look that makes them perfect for any occasion and can be paired with dress pants or skirts and heels for a polished, sophisticated look.

Despite their dressy appearance, flowy chiffon blouses are actually quite comfortable to wear. The fabric is light and breathable, which makes them a great choice for warmer weather.

The Ruffled Skirt

Ruffled skirts are a classic choice that are both feminine and versatile. This shape creates a slimming effect due to the way the skirt flares out.

This skirt is essential for women over 40 due to its ability to be universally flattering, and the idea that you can dress this skirt up or down for any occasion.

The Pencil Skirt

turtle neck oufits

If you are searching for a skirt that will accentuate your curves, a pencil skirt is an ideal choice. Pencil skirts are form-fitting, so you will have to be confident with every aspect of your body in order to pull off this look. 

Pencil skirts are often styled with a chic pair of heels or pumps and a blouse that gets tucked in. You can also add a blazer to add another level of sophistication to your outfit. 

Pencil skirts always fall either directly above or below the knees. You can choose the length of the skirt depending on what your work rules require.

If you choose to wear a pencil skirt for other occasions, know that a longer skirt length is usually viewed as more appropriate for business events.

Many pencil skirts have a small slit in the center of the back of the skirt so that your mobility is not limited. 

This style of skirt is worn by many women who work in an office or professional setting. Since a great number of women over the age of 50 end up working the type of job that requires business attire, pencil skirts are excellent.

Faux Leather Leggings

Chic Outfits for a Night Out Over 40-Faux Leather Leggings

(Faux) leather leggings offer the versatility we all love. Not only are they stylish and easy to wear with a lot of different looks, they’re comfortable! Which, let’s face it, is a major win when you’re getting dressed for a date night as an over 50 woman.

Don’t hesitate to reach for faux leather leggings when styling a nighttime look. Pair them with a flowy blouse, this adds to the comfort factor of your outfit, and a pair of booties. If you need to add a layer for warmth (or style), you can add a black blazer over the top to really dress up the leggings.

The Leather Skirt

50 degree outfits-denim jacket outfit inspo-leather skirt

Leather, or faux leather skirts, can look very flattering for women over 50s.

Besides, these skirts naturally look sophisticated, so minimal styling is required. Pair with a simple top and slip on a pair of heels will instantly make you look chic.

Sheath Dress

For women over 50s, a sheath dress is an excellent choice because it is a classic style that is both flattering and appropriate for their age. These dresses are designed to show off a woman’s curves in a tasteful and sophisticated way, without being too revealing or clingy. 

A sheath dress is a timeless and elegant style of dress that is a must-have for your wardrobe. This type of dress is typically form-fitting and tailored, with a hemline that falls just above or below the knee.

Lace Dress

There is something about lace that, no matter your age, is perfection for a date night outfit. In this case, a small touch of lace with a blouse or skirt is just the right amount.

Yes, lace can be over done! So just keep it to small doses to achieve the ladylike, grown up feel. Keep the rest of the look feminine to keep the aesthetic consistent throughout the outfit. Pearls are always a really fun accessory option for lace!

Stylist tip: when wearing lace make sure you’re aware of any layering that may be necessary to complete the look. Is the lace see through? If so, you will want to wear a camisole or slip underneath so it’s not a completely see-through look.

The Pleated Skirt

These skirts allow for plenty of movement due to their flowing nature. In order to let the skirt complement your body, you may want to wear this style of skirt higher on the waist. 

The pleats on the skirt will add texture to your outfit, which is always a great way to make your look more interesting. The pleats will also add extra fabric to the skirt, so the effect of the flare will be more extreme than in other plain flare skirts.

Being older than 50 often means that you are dressing with a more elegant fashion sense.

Pleated skirts give a dramatic flare. Falling at a mid-calf length, this style of skirt will make you look like the classiest woman in the room.

Pleated skirts are elegant and incredibly classy. They typically are made in the A-line shape, so they are both flattering and sophisticated. The length of pleated skirts you should always go for are midi or maxi skirts. 

Fit and Flare Dress

Fit and flare dresses are a popular style of dress that are incredibly flattering for women over 50. This style of dress is designed to hug the body, cinch at the waist and flare out at the bottom to create a flattering silhouette that accentuates your natural curves.

Fit and flare dresses are also incredibly comfortable to wear, as they allow for ease of movement just as long as you make sure that the ones you get are made from high-quality fabrics that feel soft and luxurious against the skin. This makes them a great choice for women over 50 who want to look and feel their best without sacrificing comfort.

The Slitted Dress

A midi dress with a slit is a perfect outfit for women over 50 for a date night, because it’s so attractive without looking too revealing. The slit not only makes your legs look elongated, but also makes the outfit look ultra feminine.

Satin blazer

Chic Outfits for a Night Out Over 40-Satin blazer

One of the best ways to style an outfit that looks unique and nighttime ready is by the use of texture. Think of fabrics like silk, sequins, velvet, etc. The reason these types of fabrics are so great is because it adds dimension and style to an outfit without the need to show a lot of skin – something that’s extra important as a woman over 50. When styling a date look, reach for various textures in blouses, handbags and even shoes – texture isn’t limited to just shirts!

Wrap Dress

Wrap dresses are actually quite universally flattering so it’s safe to say that it’s a dress style than can look good on you regardless of your age. The dress is designed with a V-neckline and a wraparound waist, creating a flattering silhouette for all body types.

One reason the wrap dress is such a popular choice for women over 50 is its ability to flatter a range of body shapes. As we age, our bodies change, but then the flexibility of the wrap dress hugs the body in all the right places, so the way it fits won’t ever be a problem.

The Slited Skirt

pencil skirt outfits

If you want to make your legs appear longer, go with a slited skirt. A slit is a flattering design that works on a skirt of any length, but it is most effective when you are wearing a longer length such as midi or maxi skirt.

Because these longer skirts come with extra fabrics, they can easily make you look swamped. However, if your skirt comes with a slit, gives you an elegant look, without making your legs look cut off.

Lace Top

It’s no secret feminine pieces like the lace tops have the ability to spice up an outfit, whether it’s for the day or evening.

To make sure your date look is complete, throw on a couple of fun accessories. It’s an opportunity to add a little more glam than you probably do in your everyday life, so play it up. Add a pair of dangly earrings, a cocktail ring, and/or an embellished clutch. The point is – have fun with your accessories and don’t be afraid to be a little ‘extra.’

Edgy Leather Coat/Jacket

The world of leather coats is vast and varied, catering to those who embrace bold styles. The length of the coat plays a significant role in determining its overall aesthetic most particularly in the ensemble of women over their 50s.

Leather coats come in a range of colors, with black being a timeless classic that never goes out of style. However, a bit of more dynamic colors may seem more fitting for mature women as the colors would bring more life and youth to your look.

Belted Shirt Dress

The belted shirt dress offers a flattering and feminine dash that’s ideal for a date night. Its fitted bodice and flared skirt create an hourglass silhouette that accentuates your curves in all the best places that will boost your self-confidence. 

Being a woman 50 and beyond, you’ll appreciate the versatility and ageless elegance of this dress and how it seamlessly transitions from dinner to dancing throughout the evening.

Denim Skirt

denim skirt with Satin blouse

Denim skirts are an absolute classic when it comes to casual wear. Many would associate denim with the younger generation, but you can definitely pull this off even if you’re over 50.

They are comfortable and practical, making them ideal for women over 50 who are always on the go as they are easy to move in and can be worn all day without feeling constricted or uncomfortable. This is important for women who have busy schedules and need clothes that can keep up with their active lifestyles.

Velvet Pants

Chic Outfits for a Night Out Over 40-Velvet Pants

Why settle for the ordinary when you can embrace the extraordinary and luxury with velvet pants for your next date night? Surely, their soft and plush texture provides a panache to your ensemble, while their tailored fit provides comfort and a flattering structure.

For ladies in their fabulous 50s and beyond, you’ll see how appealing these velvet pants are. Whether you’re attending a dinner party or a momentous concert, velvet pants are an all-around pick that captures the attention of the people around you.

For a cohesive look, pair your velvet pants with a matching velvet blazer in the same color. This monochromatic ensemble creates a shiny, uniform appearance, perfect for a dazzling date.

Metallic Dress

The metallic feel fabrics infuses a chic vibe into your look, making you stand out in any setting. Pairing your dress with a tailored blazer gives you a well-polished look, making you formal dinner-ready and runway-worthy!

LBD

One of the primary reasons why LBDs can be a classic choice for women over 50 is their versatility.

Go with a fit and flare silhouette as it can help create a slimming effect.

V-Neck Jumpsuit

Stride into the spotlight with the allure of a V-neck jumpsuit and bring the quintessential balance of elegance and modernity! 

This contemporary-style outfit will make women over 50 look in their prime 20s. However, you have to ensure you’re going after ethereal light colors like pristine white to exude an even more radiant and sophisticated aura. 

The Flared Skirt

wedding guest over 50- with long skirt

If you are on the search for a skirt that will create an hourglass silhouette and conceal your stomach all at once, flared skirts are a perfect choice. 

This skirt style is designed specifically to make your hips look larger than your waist. In order to achieve this look, the waistband of a flared skirt should rest at the smallest part of your waist. 

The longer you go in skirt length, the dressier your outfit will have to be. Floor-length flared skirts are often a part of ball gowns and two-piece ensembles that are worn to formal events. 

Many women look for clothing that can create the illusion of an hourglass shape. For women 50 and older, this skirt is the right decision if you are desiring a way to hide any imperfections under a long skirt that will still give your body a flattering shape.

You can choose any appropriate length with a flared skirt, and it will still keep the same shape you are looking for. With a maxi length, the skirt will have the most flow possible.

Plunging Ruched Dress

Chic Outfits for a Night Out Over 40-Plunging Ruched Dress

Bring out your inner goddess in a plunging ruched dress that oozes confidence and womanliness. If you’re in the 50s, dresses that enhance curves should be a top priority, and that’s where the artful ruching details come into play – they highlight your natural curves and add intrigue to your outfit.

Whether it’s a romantic dinner or a cocktail gathering, this dress, paired with sky-high heels and statement jewelry, ensures you command attention during the night!

Posted In: ClassyTrendy

Hello there! My name is Chi Li, 5'2", founder of PETITE DRESSING, the clothing line for women 5'4" & under. Are you petite and have you been frustrated with what to wear?
This is an issue few truly understand and even fewer brands truly address.
Being petite myself, I have been writing about fashion for short women since 2016 and my brand petitedressing.com has touched the lives of millions.
My styling concepts for petite women not only focus on the perfect fit but also on flattering & elongating the petite frame for a lean silhouette, optimizing the proportions.
Shop my clothing line here.

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