As we age and go through different phases of life, our relationship with clothing (and our bodies) often fluctuate or change. Depending on the stage of life you’re in, and even your career, your wardrobe needs could look very different from the woman sitting next to you. However, what I think we could all agree on, no matter what stage of life we’re in, is that we want to feel good in our clothes. Too often I see clothes marketed to older women solely for their “comfort.” However, older women want to feel stylish just as much as they want to feel comfortable. And why can’t you have it all? There’s certainly no reason that mature women can’t feel equally chic and comfortable in their clothes, and as your personal stylist today, I hope the 12 looks below prove that to you. I’ve got you covered when it comes to clothing styles for women over 50 with clothes that flatter – whether you’d like to flatter your figure, your coloring, or your overall sense of style.
The Best Clothing Styles for Women Over 50
1. silk button-down + slim jeans + duster cardigan + leopard flats
cardigan | jeans | flats | shirt | belt
This versatile look is perfect for the woman who does it all. Whether you’re headed to the office, school drop-off or lunch with friends, “jeans and a nice top” is our first formula. Why does this look work? Let’s break it down.
First, the “Perfect Silk Shirt” from Banana Republic is an easy way to elevate a classic style. Swapping out your traditional poplin or linen variety of button-down shirts goes a long way in dressing up a more casual look. Plus, silk will drape nicely over your figure, and is less stiff than a traditional button-down shirt.
Next up, your jeans. A slim pair in a dark wash will flatter nearly every body type. Slim jeans will hug your curves, but won’t cling like skinny jeans. On top, add a long duster cardigan. This will draw the eye up and down vertically to create long, lean lines. A suede belt will help to further accent your natural waist and body shape. Leopard print ballet flats are a fun nod to current trends.
2. fair isle sweater + midi skirt + tall boots
skirt | bag | boots | sweater | earrings
Holiday shop in style with this next look. When you’re dressing as a mature woman, you may find yourself leaning towards more classic patterns for a timeless look. I’ll also let you in on one of my favorite style secrets – dressing for the “essence” of a theme rather than being literal. For instance, you can give holiday vibes without styling a red and green look. The Fair Isle print is commonly associated with Christmas time and cozy vibes, making it the perfect piece for a holiday look that’s still neutral and chic.
A wool skirt follows that same philosophy. With it, try tall boots – they complement the mid-calf length of a midi skirt. Avoid showing your ankle in between the top of your boots and skirt or dress. That bit of skin can divide your body into sections that shorten the appearance of your legs. Add a vintage-style saddle bag and gold hoops to complete the look.
3. wide-leg trousers + striped cardigan + white button-down
button-down | cardigan | trousers | ballet flats | watch | earrings | sunglasses
One of the best ways (and the easiest) to create an interesting look? Try playing around with layers. Adding more pieces may seem counterintuitive to a flattering look, but it’s my favorite style tip for expressing your own personal style as well as finding that magical combination that works for your body shape.
Start this look with a pair of wide-leg trousers. Next, add a white button-down shirt to your base. On top, add a striped cardigan. As for shoes, try a pair of classic ballet flats. They’re comfortable and are ideal for an office setting with a dress code. Match your shoes to the color of your pants – it’s a great way to elongate your legs.
4. printed midi skirt + shell tank + cardigan + ballet flats
midi skirt | ballet flats | tank top | cardigan | bag | necklace
If you prefer a modest look when it comes to dressing, a shell tank is a great way to stay cool in the warmer months. It’s the perfect piece for everyday wear and layering. The absence of sleeves means it will prevent any unsightly bunching when you add a sweater or blazer over it (as a cardigan lover, this is one of my personal pet peeves).
When it comes to a flattering look for your skirt, try a small print. Certain styles of skirts are clingier than others (ahem, silk and satin can be notorious offenders), but a small print will help to provide a seamless look that flatters instead of drawing attention to any curve or the lines from undergarments/tights.
Accessorize with an accordion-style bag and ballet flats. The square-toed on this pair is a small detail, but one that updates the classic shoe to the modern day. You could also add a statement necklace, or keep things simple with a small paperclip chain.
5. emerald sweater + coordinating pants + cocoon coat + mary janes
sweater | pants | mary janes | cocoon coat | star earrings | purse
A monochromatic outfit is always a good idea if you’re looking to instantly elevate your outfit with little effort. The foundation of this monochromatic look is a beautiful emerald green from Eileen Fisher. This color is ideal for your holiday ensembles!
As we age, we often refine our sense of style as well as our list of favorite colors, fabrics, and fits. That means that many of us start to gravitate toward investment pieces. They’re known as investment pieces because of the costs-per-wear of the item – well-made pieces last a long time, and allow us to wear them many more times than fast fashion styles. Eileen Fisher is on the shortlist of many of our readers here at MCO for investment pieces and clothing styles for women over 50.
On top, layer a cocoon-style coat from J.Crew. The straight, clean lines of this coat make for an expensive-looking outfit. Starburst earrings, an accordion-style bag and Mary Janes complete your holiday dinner party outfit.
6. pleated asymmetrical skirt + black turtleneck + slingback heels
turtleneck | skirt | heels | bag | earrings
The moment I saw this skirt on the website, my jaw dropped! If you want to make a statement this holiday season, this is how you do it. Plus, I love a pleated skirt for a flattering look – the pleats and asymmetrical hemline add movement, and the vertical lines of the pleats help to lengthen your legs.
On top, keep things simple with a black turtleneck. Your skirt is the main attraction! Coordinate your accessories with a small Bordeux bag, and bevel crystal earrings. Slingback heels finish off your look – the pointed toe and lack of ankle strap help to elongate the appearance of your legs.
Related: How to Flatter Your Body With These Slimming Outfits
7. shell tank + navy blazer + pleated pants + mary janes
pants | white tank | blazer | mary janes | tote bag | watch | pearl studs
If you’re an older woman looking for nice clothes for the office that are also comfortable, one of my favorite go-to recommendations is Everlane. They offer a wide range of classic pieces in neutral colors. A majority of their styles come in a variety of different colors as well. This is good news, as you might fall in love with a piece with a good fit and want it in multiple colors!
A crisp navy jacket will be your best friend for your year-round styling. Layer it over a shell tank and pleated pants for a comfortable yet work-appropriate outfit. Or, pair it with a dress, skirt and sweater, or even shorts for a weekend look. There are so many great ways to wear a blazer.
8. top coat + lacy cardigan + blue jeans + slingback heels
heels | jeans | cardigan | topcoat | belt | earrings
I’ve started investing in high-quality cardigans this year as part of my own style evolution. The great thing about cardigans is how versatile they are – you can layer them, wear them as a top, or even turn some around for a unique blouse. Not all cardigans are created equal, but the delicate lace detail and v-neck style of this piece make it feminine and elevated. If you have a larger chest, you might try a v-neck style sweater – it helps to open up your chest area for a flattering look.
Pair it with dark-wash jeans for the perfect brunch look. Add a long topcoat in cream for a sophisticated look. Don’t be afraid to ask for help from a sales associate or tailor in order to make sure you find the proper fit. The right size clothing is key to finding the perfect fit that complements your body shape.
9. trench coat + sweater + dark-wash jeans + loafers
jeans | socks | loafers | trench coat | shopper tote | sweater
Are you a long-time fan of skinny jeans, and looking to branch out? Well, you’re not alone. For years (and years) I was a firm believer in the fact that skinny jeans were the most flattering style. And honestly, their name can be misleading! After ditching the skinny jeans, I’ve found many new styles that flatter my body much more. If you’re looking to see what else is out there beyond skin-tight jeans or leggings, straight-leg jeans are a great place to start. They still conform to the relative shape of your natural body’s lines but are more forgiving and comfortable. Plus, I find them much easier to pair with a wide variety of shoes.
The perfect pair of jeans is the magic key to a casual look that you feel amazing in. On top, try an oversized turtleneck for a cozy weekend outfit. Next, reach into your capsule wardrobe for your favorite trench coat. Add loafers, ribbed socks, and a shopper tote to complete the look.
Your Dream Wardrobe: You can find more capsule wardrobe helpful hints and tips with MCO’s free resource guides here.
10. pleated skirt + black sweater + Bordeux bag + statement earrings
skirt | heels | sweater | earrings | bag
Black is often argued to be one of the most flattering colors out there. And while that may be true, it does often depend on your complexion as well! If you are a fan of an all-black look, try recreating this next outfit.
First, start with a pleated midi skirt. As I mentioned above, it’s a great way to add a flattering shape to your lower half. On top, try a cashmere sweater. It’s perfect for the winter months but doesn’t add too much bulk. Try tucking into your skirt to highlight your natural waist, or add a belt for more definition.
Continue the monochromatic color scheme with black slingback heels, and a small Bordeux bag – perfect for an evening out.
Related: Wondering What Colors Make You Look Skinny? Read This Post!
11. wide-leg jeans + long liner coat + turtleneck + Veja sneakers
sneakers | jeans | turtleneck | coat | sunglasses | tote bag
Run your weekend errands in style with a casual jeans and sneakers look. Enter the Veja Campos: a cool pair of timeless white sneakers that we saw everywhere in Paris street style last year. If you don’t have a pair of neutral tennis shoes already, it’s high time you consider buying a pair! Whether your personal preference is Veja or Adidas or another brand, a good quality pair of white sneakers is a versatile piece in your wardrobe that you’ll never regret.
Pair your new cool sneakers with a cozy turtleneck, and jeans. Try a wide leg if you want to go for a trendier look! A woman of any age will rock this look. Finally, add a long liner quilted coat from Everlane. This will help to insulate your body heat in colder months, but doesn’t add too much bulk to your outfit.
When it comes to your tote, consider a Longchamp Le Pliage. It’s a great bag for a casual or professional look and comes at a great price point. Carolyn and I each own one, and you can read our recent review of the bag in the large and medium sizes.
12. wrap dress + topcoat + neutral flats + gold watch
wrap dress | coat | tote | flats | watch | earrings
For our final look, swap out your favorite little black dress for a gorgeous navy wrap dress from Banana Republic. Wrap dresses flatter women of all ages. The natural waistline created by the draping of the dress will flatter you in all the right places, while the v-neck helps to create space in your neck and chest area.
Add a classic topcoat, ballet flats in a neutral color, a gold watch, and pearl earrings in a gold setting to complete the look.
Ageless Style
As we age we may find that certain tweaks to our everyday style may provide us more confidence and comfort. However, that doesn’t mean you are limited to only shopping for certain pieces or from certain brands! Fashion is ageless – it’s all about creativity, and knowing yourself and your own body. Once you master that and find out what you truly feel good wearing, the rest just takes a little bit of practice. Hopefully, the looks above will inspire you as you tailor these looks to your own tastes!
Want to further level up your look and learn how to look expensive on a budget? Up Next: 11 Tips on How to Look Expensive + What to Avoid
