The 13 Fashion Essentials For Dressing Your Best Over 50

fashion over 50

Here in the second half of my “fifties,” I now know that getting older has plenty of perks to go along with the less enjoyable stuff! There are certain things in my life that I now feel better about than I ever did when I was younger.

And one thing I continue to enjoy no matter how old I get is fashion! I love seeing headlines on magazines and in the media that say things like “60 Is The New 40,” because I personally couldn’t agree more. As women of a certain age, we may be a bit older and a bit wiser, but we still have style to spare! ;-)

As a matter of fact, I would argue that fashion for women over 50 has depth and passion that the youngsters can’t hope to compete with. :-) Style is style at every age, and you don’t have to spend a fortune or build a massive wardrobe to get it!

The “fashionable fifties” (and beyond!) are well within our grasp, and it’s not as difficult or as daunting as it may seem. And I hope to prove that in today’s post, where I’ll be sharing my favorite over-50 fashion tips, including a list of 9 must-have fashion staples that women over 50 need to flesh out a fierce, fabulous, and age-appropriate wardrobe.

(Note: Although I’ve provided a recommendation for where to shop for each item, it certainly won’t be the only place you can get it! For budget-friendly options, I usually head straight to TJ Maxx, and you can always shop online thrift stores like thredUP, Poshmark, or Depop.)

Fashion Over 50: 9 Must-Have Pieces For Your Wardrobe

fashion over 50

1. Dark Mid-Rise Jeans

This is one of the very best fashion tips I can give you: Every woman over 50 needs a great pair of dark jeans. Straight-leg denim paired with the right shoes—think pumps or boots—can be a highly versatile look, perfect for both work meetings during the day or a nice dinner at night.

Make sure your jeans fit well around your butt and hips. (With any clothing item, it’s better to go up a size and get it tailored down rather than trying to squeeze yourself into something that’s too tight in certain areas.) Jeans look good dressed up or down, plus they never go out of style!

Where To Find Them: Madewell

Madewell focuses on clothes that are effortlessly classic, including denim. They have simple and modern styles that are made well, and are in line with the latest trends without looking too “trendy.”

fashion over 50

2. Fitted Pants

Wear a tailored pant for a smart and sleek look. They will flatter your figure and make you feel super stylish! You can wear them all sorts of ways, but my favorite ways to wear fitted trousers are with a silky top, or with a t-shirt and jacket.

And don’t be afraid to show your personal style with a bright color or print. A “statement pant” can be unexpected and fun! (We “women over 50” may not be as young as we once were, but that doesn’t mean we need to look serious or boring.) Fashion is all about showing your natural beauty and unique personality, so don’t be afraid to make a statement! ;-)

Where To Find Them: Ann Taylor

Ann Taylor takes a sophisticated, feminine approach to modern essentials like their wide selection of fitted pants. Whether you’re more interested in stylish or stretchy options, you’re sure to find your perfect pair!

fashion over 50

3. Pencil Skirts

This over-50 fashion tip may come as a surprise, but it shouldn’t be a surprise at all. Pencil skirts are almost universally flattering on women, have never been out of style, and they’re so versatile too! Choose one that is fitted without being too tight or restrictive, and pair it with a heeled shoe, like a bootie, pump, or wedge.

When shopping for skirts of any style, you want to look for ones that hit at your knee or below for a more sophisticated look. (A shorter skirt, oddly enough, may actually make you look older, not younger!)

Where To Find Them: Macy’s

I love to shop for skirts at Macy’s because I often find out about great brands that I wouldn’t know about otherwise. For instance, this animal print skirt is by Palette, an independent fashion shop based in London.

fashion over 50

4. Cardigans

If you’ve been following my blog for any amount of time, then you probably already know that cardigans are my personal go-to fashion piece! They’re functional year-round, either for keeping warm in cooler temperatures or just for covering up your arms. Make sure your cardigan fits well, as slouchy or baggy cardigans can end up looking a bit frumpy.

Where To Find Them: J. Crew

I think J. Crew cardigans are the absolute best (as well as their more affordable counterparts at J. Crew Factory.) The fit, the style, the array of bright colors, and the quality keep me coming back for more!

fashion over 50

5. Tank Tops

Just hear me out on this one, okay? ;-) Many women over 50 have left tank tops in the rearview, but that can actually be a big mistake! I’m not saying I wear tank tops by themselves, but I do wear them frequently when I’m layering with a jacket, cardigan, or other outerwear.

A good tank top helps smooth things out in the torso area, and they can add cute and interesting detail to an outfit as well. I recommend every woman over 50 keep a few of these handy at all times! Look for tanks that fit snugly, and that are long enough to stay tucked in to your skirts or pants.

Where To Find Them: Nordstrom

Shop at Nordstrom and you’ll find many high-quality clothing brands, especially when it comes to tank tops. From edgy to chic, Nordstrom has great tanks for all your favorite looks!

fashion over 50

6. Dresses

Wearing a dress is an easy way to feel fun and feminine! There are a few styles of dresses that work particularly well on women over fifty: wrap, sheath, and fit-and-flare dresses.

Wrap dresses should be worn with the belt tied on the side (never in front!) Sleeveless sheath dresses look great with a snug-fitting cardigan or jacket (my personal favorite look!) And finally, look for fit-and-flare dresses that hit your knees (and that have plenty of flirty swing to them, of course!)

Where To Find Them: Amazon

With free returns on most items, it’s hard to beat Amazon when it comes to dress shopping. I found this holiday-ready Calvin Klein peplum sheath dress on Amazon, and they carry options from almost any brand you could think of.

fashion over 50

7. Animal Print

So animal print isn’t technically an “item of clothing,” but I maintain that it’s a must-have style choice! Incorporating a piece of clothing with an animal print is a great way to let loose and make any outfit more fun, edgy, yet still age-appropriate.

My leopard print ankle boots are one of my favorite pair of shoes, and they bring a sassy feel to classic, casual, and dressy looks alike!

Where To Find Them: Nordstrom

Nordstrom has an excellent array of fashion for women, including chic animal print pieces. This Dolce Vita boot I found at Nordstrom has the perfect chunky heel that adds a little height without sacrificing stability.

fashion over 50

8. Timeless Turtlenecks

Turtlenecks are another one of my fashion “go-to’s!” A turtleneck is always sophisticated and stylish, in my opinion, especially in black or white. They’re really versatile, and can be layered as part of a day or night ensemble. And they’ll keep you warm when temperatures get cool, to boot!

Where To Find Them: Boden

Boden makes fashion for the modern woman that is chic without sacrificing comfort. If you like being comfortable but don’t want to sacrifice on sophistication, you’ll surely love what Boden has to offer!

fashion over 50

9. Modern Blazers

A blazer may seem like high fashion to some, but it’s actually an incredibly simple way to bring a touch of class to nearly any outfit you add it to. Opt for brighter colors to keep things fun, or stick to darker colors (black, grey, and navy) for a more professional appearance.

Blazers are tailored to come in at your natural waist, creating a flattering silhouette that shows you know exactly what you’re doing (even when you don’t!)

Where To Find Them: Pure Collection

Pure Collection is best known for their ultra-soft cashmere, but you can find other comfy and classic pieces there too, like this linen blazer. It’s soft, chic, and always looks put together!

Bonus Fashion Tips For Women Over 50 (Or Any Age!)

  • Don’t Forget Your Bag! Handbags are a timeless fashion accessory that can complement any outfit. Anyone can tote around a practical and trendy bag, regardless of age or size! (But if the latest trends in bags don’t appeal to you, a classic structured bag never goes out of style!)
  • Level Up Your Underwear Game. Underwear is the foundation of your outfit, and it shouldn’t be neglected! Make sure you’re wearing the correct size of bra, and utilize “shapewear” as needed. (Being a 50+ year old doesn’t have to mean “granny panties!”)
  • Sensual Over Sexy. For an alluring ensemble that’s still sophisticated, shop for sensual colors and fabrics as opposed to “sexy” ones. Fabrics like silk, satin, lace, and cashmere will give you a luxe look, and rich colors like burgundy, violet, and emerald green add a splash of drama!
  • Get sassy with shoes. Another one of my very favorite tips! A great pair of shoes is another outfit-making accessory that anyone can pull off. It can add a touch of class – or sass – to any set of clothing you have in your closet. If you’re worried about being uncomfortable in a pair of high-fashion heels, get some gel insoles for added cushioning.

What’s your best fashion tip?

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Jill Nystul (aka Jillee)

Jill Nystul is an accomplished writer and author who founded the blog One Good Thing by Jillee in 2011. With over 30 years of experience in homemaking, she has become a trusted resource for contemporary homemakers by offering practical solutions to everyday household challenges.I share creative homemaking and lifestyle solutions that make your life easier and more enjoyable!

About Jillee

Jill Nystul

Jill’s 30 years of homemaking experience, make her the trusted source for practical household solutions.

About Jillee


Beauty Tips

  • Hi just wanted to say thank you on the ‘thredsup” tip. I purchased 9 articles for $80. That’s less than $10 a piece. Most were like new without signs of wear (according to description) some still with tags. Lucky brand denim jacket, Vera Wang black chunky pumps, Ann Taylor black silk cardigan. I’m so excited it’s like a kid waiting for Christmas! All returnable so dont see it as much of a risk. Will update when I receive.

  • Although I’m a guy easing up on 30, I read your blog on a regular basis because you have great tips for organization, cleaning, and self care. You’re also very personable and easy to read.

    Although this isn’t one of the posts I was drawn to your blog for, I enjoyed the read and I agreed with everything I read here. I’m glad that the troll got deleted that first posted a replied when you posted this. You look great…. and the outfit in the lace skirt is hands down my favorite in the post.

  • Black looks great on you Jillee!
    100 years ago, (a bit of hyperbole here), I had my ‘colours’ (or seasons) done. Now that I’m old, those colours don’t suit me. So, it’s a good idea to update that exercise, including your makeup.

    • So many women are still ‘married to their colors.’ I am glad to hear you are not one of them! I am a fashion stylist and oftentimes have to persuade women to leave their original color comfort zone.

  • I agree with all these ideas, yet I feel that the booties cut legs at a bad spot and make legs look short and chunky…a pump-type or ballerina flat are much more elongating…and flattering

  • You are totally awesome! I love your outfits and your style. I’m 67 years old and don’t want to look like a old lady, so your style is great . Keep it up!!

  • I love that Jillee has given me a way to shop for very stylish clothing at a bargain price. I found thredup through an earlier post by Jillee and let me just say regardless of what your fashion style is, you WILL be able to find what you are looking for at some of the most amazing savings I’ve seen yet! I retired my designer tastes a long time ago because let’s face it, college for 2 kids was on the horizon and scaring the life out of us! Now I can afford to buy those designer labels I love (every now and then), put 2 kids through college and look and feel great doing it! I read your blog every day for something new I’ve never thought of; whether it’s a hack for cleaning, organizing, making gifts, baking or style tips, my life is a bit easier and better thanks to you!

    P.S. I’m in the late 1/2 of my 50’s and I “borrow” a lot of your style tips and then add my own twist!

  • Super cute and classy at the same time! I love the colors and prints, I tend to stick with too many neutrals! Thank you for this post and to thredUP for the discount!

  • My trick is PENCIL SKIRTS! Under the knee, best knitted. And short jackets that hide away a big tummy!. Makes me look 10 kilo less in an instant.
    And indeed, you look fab (as I do, and I am a young 62 old chick).

  • You look fabulous! I admire mature women that enhance their appearance with a bit of makeup and flattering hairstyle instead of looking frumpy. I’m 65 and still want to look my best. It’s nice to receive compliments, which always makes us feel good, right? You go girl!

  • Great ideas. I have some of the stuff like the Cardigans and leather jacket. I do agree there is a fine line between trying to look to young. I would do the shorter skirts if I could get my legs to look better. It’s kind of a Celiac type of rash. I’m not trying to look a certain age anymore, just trying to look good for my age.

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