You are currently viewing Stylist’s Secrets How You Can Wear Denim Like a Pro
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 at any age 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
  7. Can you wear denim in midlife and beyond?
    • Advanced styling tips for denim over 40
  8. Stylist’s secrets on wearing denim like a pro
    • Inspirations how to wear a denim skirt
    • Ideas how to style a denim jacket
    • Suggestions how to wear jeans
    • Inspiration how to style a denim shirt over 40
    • Discussed example: Denim dress
    • Explained example: Disstressed jeans
      • How to make distressed BF look great for Casual Friday
    • Discussed example: Skinny jeans

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


fashion over 40 woman in shearling motorcycle jacket and BF jeans
Wool beret, Ray Ban sunglasses, Andrew Marc motorcycle shearling jacket, London Jean boyfriend jeans, leather gloves, Yes St. Laurent bag, Rack Chevron cashmere scarf, and Clark booties


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. The fabric in bright colors or white look great too at any age. Be aware that colored denim fail to get the comfort of jeans.
  • Tailored shirts look great even in a denim-on-denim styling.
  • When wearing two denim pieces in an outfit take distinctly different shades. Add classic footwear like pumps, heeled booties, or strappy sandals. Avoid to look like a cowgirl even when you go to Western bar.
  • Jeans with a twinset or a T-shirt plus cardigan are great for Casual Friday if your dress code permits.
  • Soft denim shirt-dresses without any frills are great for summer. Pair them with sandals and a belt for the weekend. If the dress code allows wear it 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 of the scarf repeat the colors of the sandals or vice versa.


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 boyfriendsdenim outfit for fall in neutral colors Go for an all neutral color look with a striped T-shirt, denim jacket and matching linen pantsinfluencer 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

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


stylist illustrating how to look ageless in blue with a denim jacket, snake print, suede with gemstone hangersJ. Crew snake print skirt, Vince Camuto boots, Hermes collier de chien bangle, August silk top, Judith Leiber belt, DIY gemstone earrings (all own) and tights c/o Hipstik legwear


Denim skirt outfit idea

Many stylist tell you not to wear denim skirts. Their main argument is the stiffness of the fabric. However, the degree of stiffness depends on the weight of the fabric. Furthermore, stiffness has not to mean it is a bad style/look. When you are straight up 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, creates curves because of the stiff fabric! The cut fits my sleek style.
  • If you go for distressed jeans, make sure it is obvious that you bought them that way. Avoid that they look like a leftover from your time 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 like 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

Can you wear denim in midlife and beyond?

You love your denim as much as the next gal, so wear it. You want to look polished, not floppy, or frumpy, but also not like trying too hard or even worse, not trying at all. Going beyond the basics in wearing denim over 40 is like to balance on the sharp side of a carving knife. The fabric is associated with casual and weekend. Wearing it can easily look frumpy or like wearing a uniform.

Advanced styling tips for denim over 40

First let me give you some outfit inspirations.

fashion blogger in Italian jeans and twinset with satchel bag

fashion book author in bootcut jeans, faux twinset and loafers
Oliveo mid rise, Italian denim bootcut jeans, GG loafers, Prada bag, Brooks Brothers sweater, unbranded long cardigan, statement malachite and lapis necklace, Kieselstein Cord belt and buckle and Hermes collier de chien bangle (all own)


over 50 years old stylist in high rise wide leg pants with denim shirt

style blogger in pants and denim press button shirt with belt and scarf

over 50 years old woman in shearling motorcycle jacket, plaid pants, denim top, beret, gloves, booties
Great Northwest denim shirt, Kieselstein Cord belt, native buckle, Pendleton glen check pants, Coach Chelseas, Anne Klein scarf, Hermes collier de chien bangle, LeatherCoatsEtc beret and gloves, Andrew Marcs shearling motorcycle jacket, Kate Moss for Longchamp bag and statement studs (all own)

Stylist’s secrets on wearing denim

  1. Stay away from superwide bell-shape or super-distressed. Both extremes look ridiculous at any age. While a straight cut is a classic, pairing it with shoes is much more difficult than for skinnies, or a slight bootcut.
    • Pairing jeans with a button-down shirt, scarf or pearls, pumps and a blazer is a fool-proof business casual look to try. Paired with a white shirt is an American Classic.
    • A turtleneck sweater with jeans and blazer also falls in this category.
  2. Many stylists advise against wearing a denim skirt over 40 due to the stiffness of the fabric. However, when the cut is to the advantage of providing shape to a straight-up-and-down body and the skirt is above the knee, it can work to your favor. Not sure what body type you have? Detect your body shape type with this free online quiz.
    • If you wear a denim skirt, stay out of dressing like a cowgirl. Do not add a plaid shirt plus fringe leather jacket, cowboy boots and a hat unless you go to a western bar, Wild West festival or outdoor concert. You would look otherwise like Rosie in Disguise.
    • Style the denim skirt like you would style a corduroy skirt with a striped Tee or polo shirt. Or style it like a black pencil skirt with a white button-down shirt and black or nude pumps.
  3. Denim jackets are a nice way to style a dress down. Click To Tweet
    • Try a denim jacket as an alternative to a cardigan.
    • Belt your denim jacket and/or wear it under a vest.
    • Pair a denim jacket with a romantic dress or skirt, a lace dress or sequin skirt for an unexpected going out look.
  4. Denim-on-denim looks best with two different washes, but same texture. Click To Tweet Think one of the denim-on-denim pieces just was  washed more often than the other.
    • If you aren’t tall like Karlie Kloss don’t go for her Texas tuxedo, i.e. denim everything.
    • Soft fabric denim shirts look great with dark wash jeans, corduroy or leather pants and even a black pencil or a classic tweed skirt. Go for a tailored cut to look polished.
    • Try a denim piece with a white (or colored) denim piece.

Inspirations how to wear a denim skirt

mature woman looking great in a denim skirt Weekend look with dark-wash Oliveo denim skirt with a striped Jeanne & Pierre sweater, GNW tights, Prada bag, statement belt, scarf and Puma silver sneakers (all own). The color and posh style of the sneakers plus the accessories (scarf, statement belt) give the casual outfit a stylish look
midlife woman looking great in a denim weekend outfit Classic American weekend outfit with straight Oliveo denim skirt, Kieselstein Cord belt, H-buckle, Anne Klein T-strap pumps, statement necklace, Hermes collier de chien bangles (all own), and a striped T-shirt c/o Marine Layer

Ideas how to style a denim jacket

influencer in white print dress with white denim jacket fuchsia bag Eli Tahari printed sheath dress with white denim jacket, Gloria Vanderbit red pumps, 3.1 Philip Lim tote, and Paloma Picasso sunglasses
influencer wearing a lace pencil skirt with denimLevis denim jacket with eShakti lace pencil skirt, Festina watch, and Prada bag for a posh Casual Friday look
fashion blog content creator in a plaid dress with denim jacket Ruby Belle plaid sheath dress worn as skirt under an oversize Great Northwest denim jacket with leather motorcycle vest, flower and multiple strings of beads statement necklace, opaque GNW tights, and Harley Davidson motorcycle booties

Suggestions how to wear jeans

influencer in distressed jeans, white blazer striped top, pumps London Jean boyfriend jeans styled for Casual Friday with a striped T-shirt, linen blazer, structured bag, statement belt, DIY necklace, Hermes collier de chien bangle, and Ralph Lauren silver pumps (all own)
mature woman wearing skinnies J Brand skinnies styled for a comfy, but polished weekend winter look with Brooks Brothers mock turtleneck sweater, pearls (all own), and a light trench coat worn as jacket c/o Lookbook Store.

Suggestion how to style a denim shirt over 40

influencer in leather suit with denim shirt Great Northwest denim shirt styled as a jacket with Studio Sierra leather skirt and jacket, GNW tight, Harley Davidson booties, and GNW cardigan worn as a top (all own) for a warm winter Casual Friday look
woman wearing a denim shirt under a dress Great Northwest denim shirt worn under a GAP LBD with DIY statement belt, GNW polka dot tights, Hermes collier de chien bangle, and L.K. Bennett pumps (all own) for an office-appropriate look

How do you style your denim? Do you wear denim-on-denim? What’s your favorite outfit with this fabric? I am curious.

Discussed example: Denim dress

In the look shown in the photos below, the color scheme is given by the plaid scarf, red, blue, black.

mature woman in denim dress

older fashionista looking professional in denim
Liz Claiborne denim dress (shortened), L.K. Bennett navy patent leather pumps, GNW black tights, Hermes enamel bangles, Moda International cardigan dyed red, BCBG belt, and unbranded red-black-blue plaid scarf (all own)

Explained example: Styling distressed jeans

What about distressed jeans? You surely have read the countless memos in various fashion magazines, the fashion sections of newspaper, and style books:

No distressed jeans after 40.

Well, I am a midlife blogger, and proud of it. And after buying this distressed jeans I thought “I hesitated way too long to get my own pair.” I have loved distressed BF jeans ever since I saw them the first time when Kate Holmes wore a pair. About a year ago, my best friend bought a pair of sweatpants with a distressed print. That made me even more to want my own pair of distressed BF jeans.

midlife fashion blogger looking posh chic in distressed BF jeans

mature style blogger in polished style with distressed jeans
Outfit details: Loft distressed BJ jeans, unbranded white short sleeve tailored linen blazer, Madonna True or Dare floral patent leather pumps, Tissot watch, Kieselstein Cord belt and buckle, vintage Esprit shoulder bag, Hermes collier de chien bangle, Brooks Brothers silk cashmere knit sweater (all own) and  white jade and black onyx necklace c/o Almo Jewellery


When I saw these sweatpants the last time, I mentioned it. My best friend was like “do you really want to pay more money for a pair of jeans that is already broken?” “Sure, the distress is another step in the production process. That’s why they cost more.” “Right, but they are ugly.” “Then why did you buy sweat pants with a distress print?” “They are not broken.” “But they have an ugly print?” We both LOL. 🙂

After doing some insomniac online shopping I got these. When I wore them the first time, my best friend pointed at the distress and said “yack”, but loved them in the overall outfit/look so much to take not only one photo, but one from from all angles. 😉

Wear what looks great on you and forget about the rest. #personalstyle Click To Tweet

Always experiment with new things you like. Some items that are first a trend – like distressed BF jeans. Later, they  become a classic. Prior to that when worn with classics, they just add the little twist. Remember, a twist keeps a classic look from being boring. Classic with a twist. The distress as the surprise.

How to make distressed BF look great for Casual Friday

Wear distressed jeans with a blazer, knit silk or cashmere sweater, high heels and accessorize with a necklace that also builds on the unexpected. In the example above, it’s being bold and delicate at the same time. The blazer should be high quality and have a  tailored cut. Add a statement belt. The patent leather high heel pumps add polish. In one sentence, style distressed jeans with luxury items for a classic with a twist and stir clearly away from anything “frumpy”.

Discussed example: Skinny jeans

This example pairs skinny jeans with an ethnic shirt for a western vibe Casual Friday work outfit. The ethnic top was a gift of a girl friend of mine. She bought it in India for me when she visited her family during the winter break. To keep the look from going Bohemian or 70s, add a luxury bag and a classic trench coat. You can give the outfit a little edge with a funky or unexpected pop of color like neon yellow pumps in the inspiration below.


Stylist tip: Always repeat a color at least twice in an outfit like in this example neon yellow and sunflower yellow.


mature stylist in an outfit with ethnic shirt styled in a western way with skinnies and pumps

older lady in posh chic Indian ethnic shirt with jeans

old woman in a casual posh jean outfit
Outfit details: Burberry trench coat, Ray Ban sunglasses, sunflower yellow Longchamp pliage de cuir bag, unbranded white Indian ethnic embroidered top, Hermes Medor watch, J Brand jeans, and neon yellow Christian Louboutin heels (all own)


When you like any of these outfit inspirations, it would help me if you pinned them to your own Pinterest board. It’s a great way that your friends, family, and others can see them too.

When you liked this post share it with your friends by tweeting them: Read these great tips on how to look awesome in denim over 40. #agelessstyle #fashionover40 Click To Tweet.

You may be also interested in my guide on  styling  Plaid, or reading posts of the Ageless Style Series like how to wear the Global trend.

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Photos: G. Kramm

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