Ultimate guide how to look great in denim over 40
Escada denim booties, Vittoria Verania blazer, Coolibar shirt, unbranded necklace, H buckle and belt, Hermes collier de chien bangle (all own), flare jeans c/o Femme Luxe

Denim is an American and casual classic. This guide covers how to best wear it over 40 and not look like trying too hard or not trying at all.

  1. Jeans are a casual wardrobe essential
    • No pants at school is over
  2. Stylist’s secrets of looking great in denim over 40
  3. Easy examples of great denim outfit ideas to try
  4. Denim skirt outfit idea
  5. Debatable looks
    • Outfit inspirations with skirts and distressed bf
  6. What does not work

Jeans are a casual wardrobe essential

Today jeans are an essential of the everyday wardrobe for women of all age in the American West and Midwest like the Dirndl is an office appropriate summer dress for every women in the Munich area. Black jeans and a black blazer and top are a NYC standard uniform. Denim is a staple. This guide addresses how to wear denim over 40 in a sophisticated way for business style, Casual Friday, weekends and date night. It provides explanations and photo outfit ideas to illustrate how to style denim like a pro.

No pants at school is over

The baby-boomers remember the times when we were not allowed to wear pants at school, not to mention jeans. Getting my first pair of jeans was a big fight with my mother. And we all fought for wearing jeans and pants, right? Why should we give up on them now? We were the trendsetters back then.

Now we set the bar how to wear jeans in ageless style.

over 50 years old woman wearing posh denim-on-denim outfit

mature woman in white denim boyfriend jeans with blue denim jacket
Outfit details: Star denim jacket, London Jean boyfriends, Madonna True or Dare floral pumps, Prada bag, Tissot watch, Hermes collier de chien bangle, statement necklace, and Saks Fifth Avenue cashmere sweater (all own)

Stylist’s secrets of looking great in denim over 40

  • Great fit is key. Your bum should look great from the back – have a photo taken by the salesperson. With respect for the fit think Jane Birkin in the 70s for flared jeans, strive for a fit like Brook Shields in the Calvin Klein ads in the 80s, or Cindy Crawford in her straight cut in the 90s. The length should be 1/8 of an inch (3.3 mm) above the ground in the shoes you plan to wear with your jeans. Sit down and make sure the Y is not showing. Always go for a rise that is above the hipbone in the front. If you go for a rise above the navel, make sure to style it like Marilyn Monroe did. If you find a brand and cut that flatters you, stay with it until they change the cut.
    • Buy the smaller size when on the fence between sizes
    • Make the real life test. Sit down and look whether a gap shows up in the back or the top of your thongs shows like a diving whale’s tail. If any of these incidents happen, this jeans is not the right fit.
    • When you are short-waisted you can go with lower raise just above the hip bone, while long-waisted women look better in mid-raise or high-waisted jeans.
      1. Stay out of mommy jeans land! Even straight jeans should fit tight thru the waist, hip and at the bum.
      2. Always go for a dark wash.
      3. Denim in bright colors or white look great too at any age.
  • Tailored denim shirts look great even in a denim on denim
  • When wearing denim on denim always go with distinct different shades and accessorize with classic items like pumps, heeled booties, or strappy sandals. Avoid to look like a cowgirl even when you go to a western-style Night Club.
  • Jeans with a twinset or a T-shirt plus cardigan are great for Casual Friday if your dress code permits denim.
  • Soft denim shirt-dresses without any frills are great for summer with sandals and a belt for the weekend and – if the dress code allows – with pumps or slingbacks for work.
  • Depending on your body shape, the right-cut denim jacket is great worn over a summer dress as an alternative to a cardigan
over 50 years old stylist in jeans skirt
Jones New York silk top, Oliveo skirt, Anne Klein nude slingback, D&GM sunglasses and statement bag (all own)

Easy examples of great denim outfit ideas to try

Scarves are perfect to up the style factor of an outfit when you know how to style with scarves. The next inspiration features a rolled-up jeans, strappy sandals, a gray T-shirt, and sunglasses LOTD with a hand-painted silk scarf. The scarf is hand-made in Leipzig, Germany. The leopard painted on the fabric has a face like my cat Kasimir. The colors picked up by the colors of the sandals or vice versa. The bag is an exchange. My girlfriend had gotten this high-end bag from a great-aunt, However, she is more the “California Casual, I love my backpack” type of gal. I once got a nice leather backpack, but I never wore. It was not me at all. Thus, we just trade these bags. I really love this beige snake print bag. It is so me.

cute updress of jeans and tee for picnic

stylist in sunnies, jeans, Tee, scarf, gladiator heels
Outfit details: London Jeans Boyfriend jeans, Carhartt T-shirt, painted silk scarf, Studio gladiator heels, Kieselstein Cord belt and buckle, and Ray Ban mirrored sunglasses (all own)

Here some further visual denim styling inspirations for stylish women over 40.

Ageless Style in a denim jacket for Casual Friday Denim jacket instead of  blazer for Casual Friday. The pumps, sweater, structured bag and pants make the look business casual. The color palette sticks to neutrals
over 50 years old women wearing denim on denim with tailored jacket and denim shirt dress for Casual Friday Example for denim on denim with a shirt dress and tailored jacket in different washes styled with a satchel, T-strap pumps, and belt for a Casual Friday office look in fallmidlife blogger wearing a tailored denim shirt with linen pants for Casual Friday Tailored denim shirt in a medium wash with linen pants in jeans cut accessorized with a statement belt and slingback pumps and structured bag for a Casual Friday lookstreet style fashion blogger in denim coat and dress with leo tights Wearing a denim coat as a statement piece with boots and a structured bagmidlife woman looking posh casual in white bf and a gingham shirt Gingham shirt and floral patent leather pumps give a feminine vibe to white boyfriendscasual Friday work outfit for fall in neutral colors Go for an all neutral color look with a striped T-shirt, denim jacket and matching linen pantswoman in golden leather skirt with denim jacket Jeans and a leather biker coat are a classic combination. Switch it up with a leather skirt and a denim jacketstyle blogger Nicole in DIY shirt, belt and skirt with Vara pumps Go for a casual look with a patched shirt and animal print skirt for the weekendmature street style Wear your jean jacket with a plaid skirt, boots and graphic Teecasual chic mature style blogger in denim dress with pants Dress over pantsover 50 years old fashion blogger in denim coat and dress with leo tights Coat

older woman in tailored denim jacket styled for Sunday brunch in summer Tailored jacket worn with striped T-shirt, white leather skirt, saddle bag and plateau sandals for a Sunday brunch

mature woman wearing boyfriends in a business casual style Styling boyfriend jeans for a business casual look by adding a blazer, a striped button-down shirt, white pumps, pearls, and a structured bag

#styleover40 mature woman wearing skinnies for the weekend fall look Fall weekend outfit with skinnies, a leather baseball jacket, booties and striped T-shirt

midlife woman in double denim with high waist jeans and denim shirt Two washes: To create interest add a statement belt. Add pumps for a feminine touch

over 50 years old woman in polka dot dress with denim jacket fall wardrobe Belt an oversize jacket for shape over a midi dress

midlife blogger in lace skirt, sequin patch denim jacket, nude pumps and mirrored sunglasses Try sequins and denim with a lace skirt for a glam, casual look

Nicole of High Latitude Style wearing a blue, gray silver casual look with DKSUKO robber booties Try a denim skirt with rainboots

woman in monochromatic fall outfit with colored jeans and matching hat Try colored jeans with a kacket and hat in fall

over 50 year old in business casual look Add a faux collar to your jean jacket with a business casual work look

50+ Alaskan in French inspired look French inspired look with wide pants, beret and blue jacket

Alaskan fashion blogger with wide pants, knit sweater, denim jacket September look White or colored denim jacket

Denim skirt outfit idea

Many stylist tell you not to wear denim skirts. Their main argument is the stiffness of denim skirt. I agree that they may be stiff depending on the weight of the fabric, but I disagree that stiffness means a bad style/look. When you are straight up and the stiffness is not a problem. The following photos show a winter look that would work for Casual Friday.

posh casual work look for women in midlife

Fashion blogger in casual jeans skirt outfit with sweater and tartan scarf
Oliveo dark denim skirt, Brooks Brothers sweater, Celine bag, L.K. Bennett blue patent leather pumps, DIY belt buckle, unbranded tartan scarf, pantyhose and brooch (all own)

Many stylists disagree about distressed jeans over 40 and denim skirts. Here they even disagree whether distressed jeans and/or denim skirts are a no-no to begin with, or just for a certain age.

flyer how to look great in denim over 40 showing gray hair woman in jeans jacket

General rules are

  • Whether denim skirts look great or not on a women of any age depends on her style, her body shape, the skirt’s cut and how she styles it. A tailored cut straight along the tights, dark, above the knee denim skirt, for instance, looks great on me. It gives me some curves because the fabric is stiff! The cut fits my sleek style.
  • If you go for distressed jeans, make sure it is obvious that you bought them that way, i.e. that they are not a leftover from your time back then in college. 😉

Outfit inspirations with skirt and distressed BF

mature woman in a denim skirt for Casual Friday Denim skirt worn with a “fake twinset” of a sweater and GNW cardigan, Kieselstein Cord belt and buckle and BP espadrilles for a Sunday brunch

stylist posing in sweater, blazer, jeans, heel and various accessories Midwash ripped high-waist jeans with leggings underneath for winter

 distressed denim for the mall or weekend Styling distressed boyfriend jeans for a stroll at the mall or Casual Friday. The silk scarf, striped T-shirt, statement belt and pumps elevate the look and leave no doubt that the distress is on purpose, i.e. not caused by wear

Fashion over 50 woman in distressed jeans Jeans and shirt with statement cardigan

When you liked the outfit ideas of this post, and want recipes for all kind of dressing situation in midlife, buy my book How to Dress for Success in Midlife.

What does not work

  • Cut-offs. Sorry, but they are for high school girls during the summer break.
  • Any baggy jeans with a rise above the navel
  • Acid wash, dirty wash, overly light washes, paint or jeans with embellishments, overly distressed denim items, patchwork denim clothes
  • Wedding cake-like cuts for denim skirts
  • Denim jackets cropped so short that the kidneys are free and the breast is just covered
  • Denim-on-denim with the same shade
  • Mommy jeans

What is your opinion on denim skirts? What do you think about distressed jeans? Yay or Nay? What are your style challenges when it comes to wearing denim? Let me know so I can help you.

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You may be also interested in reading the posts of the Ageless Style Series on Plaid, and Global Inspirations.

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Photos: G. Kramm

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