12 Style Essentials That Make It Easy To Get Dressed


The key to having a greatĀ wardrobe is understanding what looks good on you, works for yourĀ lifestyle, and makes you feel confident. Your style should be an extension of your personality because it expresses who you are without saying a word. Whether you prefer bold colors, unique prints, or minimalist designs, make sure yourĀ wardrobeĀ reflects whoĀ youĀ are so that you feel confident and comfortable in your own skin. Your style essentials will be as unique as you are because itā€™s about wearing what you love and what makes you feel your best. Here are 12 style essentials for women over 50 that may work for your wardrobe.

When shopping for these essentials, quality should be a priority over quantity. Pieces made from good materials will last longer and often look better. Additionally, fit is crucial because clothes that fit well, look more flattering and feel more comfortable.

QUINCE WOOL COAT / TALBOTS SLIM PANTS / SOCK BOOTIES

Trends come and go and can be an important way to keep your look current, but they should not make up the essentials of your wardrobe.

1- Style Essential – Quality Handbag

DEMELLIER “VANCOUVER” SHOULDER BAG / MANGO OVERSIZED COAT

Choose a handbag that speaks of quality rather than a specific brand name. Look for even stitching, seamless zippers, and durable materials. A handbag makes a subtle yet powerful statement about your style and attention to detail. If designer handbags are in your budget and you enjoy them, go for it. Faux designer bags scream desperate, so I would avoid them at all costs.

2- Style Essentials Over 50 –Comfortable Flats 

CLARKS JULIET LOAFER

No woman lives her entire life in heels, especially in her 50s. By this age, our feet have been through a lot, so comfortable and stylish shoes are mandatory. Supportive loafers, elegant ankle boots, and sporty casual sneakers are all part of the current fashion scene.

There are plenty of brands making stylish flats these days, including Clarks, Easy Spirit, Vionic, and Naturalizer. These brands are well known for their focus on foot health and comfort while also keeping up with fashion trends. Comfortable yet stylish shoes for women over 50 can be found at all price points. If you need some help sourcing ones for your wardrobe, you may enjoy these posts-

Best Comfortable Womenā€™s Shoes for Fall

Best Black Dress Shoes for Women Over 50 Your Feet Will Love

MORE COMFORTABLE FLAT SHOES

3- Style Essential over 50 – Flattering Lipstick

MERIT SIGNATURE LIPSTICK IN “BERRY”

Most women over 50 benefit from the lift your face gets from a swipe of flattering lipstick. Opt for a shade that brings out the best in your complexion. Overly brown and dark shades can be aging so choose a color that enlivens your face. In 2024, the trend is leaning towards sustainable and nourishing lip colors that enhance rather than overpower. That said, if rocking a red lip is your signature, go for it!

You may also enjoy- How To Choose A Flattering Lipstick After 50

4- Style Essential – Great Fitting Denim Jeans

The best blue jeans for women over 50 are the brand and style that are comfortable and flattering on your body. A well-fitting pair of blue jeans will be a versatile workhorse in your wardrobe. Some brands are best suited to women with curvy shapes, and others work better on slim hips. Experiment until you find the best fit for your silhouette, then invest in a classic dark denim pair in a straight leg for the most versatility.

classic dark wash straight leg jeans wardrobe essential on woman wearing white shirt and black sneakers
SIMILAR STRAIGHT-LEG JEANS / WHITE SHIRT / SIMILAR BELT / BLACK SWEATER / SHOULDER BAG / SLIP-ON SNEAKERS

Talbots, Loft, and Ann Taylor all make jeans in curvy and straight designs. I prefer high-rise jeans that keep my tummy in check and prevent muffin a top. If you have a shorter torso or are petite, mid-rise jeans may hit closer to your waist and be a better option for you. Leg shapes and rise continue to evolve, so stay abreast of what’s current and update yours to continue looking modern.

MORE DARK WASH STRAIGHT-LEG JEANS

5- Style Essential – Properly Fitting Bra

A well-fitted bra is crucial for comfort and your silhouette. Get a professional fitting regularly because your body changes, elastic stretches, and bras don’t last forever. Invest in quality bras that provide the support you need, but know that you needn’t spend a fortune to get a good one. I also suggest a few pieces of comfortable shapewear. 

well fitting bra which is a wardrobe essential
SOMA ENBLISS WIRELESS BRA

Gone are the days when I’d be willing to dislocate a shoulder to get into my control slip. These days, the fabrics are softer, more flexible, and much comfier while still smoothing things out. Remember, shapewear isn’t intended to take pounds off your look; simply smooth lumps and ridges so your clothes look better.

You may also enjoy my round-up of the most comfortable bras for women over 50 here.

6-Contemporary Eyewear Style Essential

Glasses are often the first thing noticed, so be sure your frames are modern and flatter your face. Rimless glasses are lightweight and extremely comfortable, but they tend to add years to your appearance. Read up on what’s current and update yours to wire or plastic frames in a contemporary shape and color. Here’s more on finding flattering frames for your face shape.

woman wearing modern eyeglass frames with knit blazer and cashmere tee
I FOUND THIS FRAME I LIKED AND HAD THEM PUT MY RX IN THEM.

7-Versatile Coat

Depending on your climate, a quality coat is an important component of a well-rounded wardrobe. Look for timeless designs that complement various outfits and suit your personal style. If your taste runs to boho, your coat will be full of unique details. If you live a rural or active lifestyle, it may be a puffer jacket or parka. Women living in warm climates can also benefit from owning a coat that’s versatile for travel, like a trench coat.

woman wearing a trench coat, sweater and pants which are style essentials
TRENCH COAT / SWEATER / PANTS / BOOTIES

MORE TRENCH COATS

8-Stylish Accessories

Some women don’t feel properly dressed without a pair of earrings, and for others, it’s a necklace. Whatever your preference, stylish accessories are what add personality to your outfits. You can find unique artisan pieces on Etsy, craft fairs, and while traveling. Many of us also have inherited pieces that have sentimental value. So whether you have a statement look that includes a pin (they’re back!) or involves a stack of bangles, the right accessories will tell the world a lot about who you are.

9-Knitwear For Layering

Sweaters and cardigans are essential in most wardrobes unless you live in a tropical climate. Look for high-quality knits in natural fibers so they hold up better over the long run. Cotton, bamboo, wool, cashmere, and silk are always a wise investment. If you’re allergic to wool, there are lots of synthetic blends available. Knit blazers are a great option for women who love stretch, along with the polish of a blazer.

KNIT BLAZER / STRIPED CARDIGAN / JEANS / SNEAKERS / SIMILAR BAG

10-Little Black Dress

A ‘little black dress’ or its equivalent in another neutral shade that suits your taste, silhouette, and coloring is a mainstay in many women’s wardrobes. It should be adaptable for various occasions, well-fitted, and make you feel confident whenever you wear it. I’m an advocate of owning a simple, dark, unmemorable style dress that can be pulled out at a moment’s notice for a sudden funeral or somber occasion. If the style is simple, you could also dress it up for dinner out.

11-Modern Pants Style Essential

Tailored pants in neutrals like black, navy, or even softer earth tones offer lots of versatility in your wardrobe. Whether you prefer sleek silhouettes or relaxed fits, ensure they flatter your body shape and match your lifestyle. I like my pants to have a bit of stretch for comfort, so this is a personal decision. Right now, straight and wider legs are popular, but you need to buy what you feel best wearing. If tailored isn’t part of your style formula, choose pants that are. The point is owning pants other than jeans.

KNIT TROUSERS / SIMILAR BELT / BIRDIES FLATS

12-Elegant Loungewear Wardrobe Essential

Every woman’s definition of elegant loungewear will be different, so just ensure you feel fabulous in yours. Even if no one sees you but you, you’ll feel your best in a beautiful robe and comfy slippers in pretty colors that are nice enough that you’d feel confident if you had to answer the front door.

With growing awareness of environmental impact, incorporating sustainable fashion pieces is not just trendy but responsible. Look for brands that prioritize eco-friendly practices and materials.

What would you add to this list for 2024?

Thanks for reading, and be sure to wear what makes you feel confident.

24 Comments

  1. I haven’t received your emails thr last few days. Could you please add me to your list? Thank you!

    1. Iā€™ve added you to the list.

  2. I agreeā€¦.we just have to ā€œcareā€ that we look our best.
    A little lipstick and a small touch of eye makeup make you look so much better.
    But I so agree with Pam ā€¦.a good hair Is very important.
    My English friend always reminds usā€¦.ā€ Your hair is. Your crown ā€œ

  3. I’m glad that you mentioned that the “little black dress” doesn’t have to be black. For those of us who look ghastly in black, navy or another neutral can be so much more flattering and still just as versatile.

  4. These are all great things to keep in mind when putting together an outfit. Can’t think of anything more to add. Thanks for the inspiration for 2024.

  5. Jennifer,
    I would add being mindful of your posture. Poor and slumping posture can make ANYONE and ANY garment, no matter the size, shape or color look dumpy and shabby.
    On a personal vent, does anyone else feel shopping has become a chore and a hassle. Inventory in some stores is slim. Online ?ā€¦ ok sometimes but product looks cheap in real life or color is not as displayed online. $ for S/H and more $ to send back sometimes
    Aaaaaarrrgghhh ! Frustrating and definitely not as enjoyable as it once was. Maybe Iā€™m just feeling curmudgeonly today. Rainy, cloudy and dreary in my neck of the woods today. Have a good day.

    1. I agree, posture is so important. I hear you about the shopping frustration!!

  6. Thanks for the list! I would add a stylish tote bag. I used to always buy very large purses so I would have room for everything I could possibly need for everywhere I could possibly go. But I really prefer the look of smaller handbags; I think very large purses can look like a “mom” or “grandma” bag rather than a fashion accessory. So now I also have a stylish tote that I only take when I actually need the room. I use interior pouches so it takes only a few seconds to transfer what’s in my handbag to my tote and back again. Game changer!

    1. Brilliant and I totally agree!

  7. Super list Jennifer and the only thing I might add to it depending upon one’s location (and would go lovely with those coats) are; head wear as in a hat/scarf, hood/toque/snood and for the hands conventional or convertible fingerless gloves/mittens or wrist warmers. -Brenda-
    P.S.: Where I am, thanks to the late arrival of Old Man Winter our weather has just taken a nose-dive. Brrrrr with lots of snow!

    1. Great addition. Hats are hugely important in my wardrobe too. Itā€™s cold and stormy here too. Stay warm Brenda!

  8. The only addition to your list that may apply to me is my hair cut and style. I do feel our unique personalities influence our choices of clothing, makeup and hairstyles. I prefer a more approachable overall style. My lip color is more subtle, my choice of color is more neutral. I prefer to add my personal touch with accessories.
    The very last but maybe the most telling accessory that we all have is our smile. Today, more than ever, this is so critical to keeping a more positive outlook on life!
    Thank you for a thoughtful blog this morning!!

    1. Yes, yes, yes!! I totally agree Jan. Have a great day.

  9. I always enjoy your posts. You are so stylish and your classic choices are right on! Thanks for the suggestions and ideas to update my look. Just because I am retired doesnā€™t mean I should only dress in sweatpants! Love your ideas!

    1. There are so many great options for us to elevate our casual look.

  10. Rhoda Clark says:

    I absolutely love, love, love this post. Perfectly timed because Iā€™m in the process of clearing out my closet. Iā€™m trying to pair it down to what I actually love and wear, rather than having a bunch of items that I may or may not ever put on. I invested in a simple black dress that can be worn to a funeral, but can be dressed up for a night out or a special occasion. lol, here I am, 77 this month, and this is my first lbd!
    Everything you have listed are great recommendations. Thanks to you I now have a black dress shoe that I can actually wear and be comfortable. I have a very narrow foot and a high arch which makes it difficult to find a dress shoe. I love a simple pump, but the way my foot is made, I step right out of a simple pump. And, of course, there is the heel height to consider.
    Thank you again for giving us suggestions that we can really use.

    1. Iā€™m so happy to hear that Rhonda. Thanks for reading.

  11. Great post! That Merit lipstick is your best find of 2023. The formula is incredible! I love the Fashion/berry color (fair/neutral skin, salt and pepper hair/dark winter) and Iā€™ve asked them for more cooler colors. What I would add is a well fitting blazer in a cut and length flattering to you And I hope you will give a review on the Demillier. I am looking at the same color!

    1. I love that lipstick too. My favorite shade for everyday is their Millennial for me fair skin. I hope they make more cool colors too.
      The Demillier is beautiful!! The color is perfect but the size is more compact than I usually need for everyday. I seem to find that about many bags so maybe I need a smaller wallet šŸ¤£
      I love the way it clasps but Iā€™m not crazy about the gold. If the clasp was silver, it would be perfect!!

      1. Agree re the gold clasp. A smaller wallet is key for those structured bags. Iā€™m still trying to find the right one. I have a few that work for travel but not every day and all of my cards. Iā€™m experimenting with a simple small pouch and wristlets can work. You can keep more and more cards and ids on your phone bit that doesnā€™t work 100% of the time.

  12. I’ve been on the lookout for a ‘little black dress’ for a while now. Something understated that can be dressed up or down. Suitable for all sorts of occasions. And something that is not about to go out of style in a year’s time. Any suggestions?

    1. Iā€™m on the same hunt and will keep you updated on what I find.

      1. Remember that Amazon Ouges dress you posted in a gorgeous blue pattern (purchased and love). I also got it in black and itā€™s now my LBD. Washes and travels well! Another outstanding Jennifer find!!!

      2. Awesome, thanks!!

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