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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. Read how you can wear denim like a pro.

  1. Jeans Are a Casual Wardrobe Essential
  2. Tips to Buy the Right Denim for You
  3. Stylist’s Secrets Wear Denim Like a Pro
  4. Discussed example: Denim Dress
  5. Discussed example: Skinny jeans
  6. Easy Examples of Great Denim Outfit Ideas to Try
  7. Debatable looks: Denim Skirts or Distressed Jeans
    • Denim Skirt Outfit Ideas
    • Explained example: Disstressed Jeans
  8. Can you wear denim in midlife and beyond?
    • Advanced styling tips for denim over 40
  9. What Does Not Work?

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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.



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


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.


influencer lobbing to wear denim like a pro
Levis jacket, Nicole fall sandals, Hipstik pantyhose, Smithsonian graphic Tee, Prada satchel, Hermes collier de chien bangle, AMS umbrella, skorts c/o Coolibar and watch c/o Nordgreen


Tips to Buy the Right Denim for You

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. It’s not the 1990s anymore.
  • 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 fails to get the comfort of jeans.
  • Soft denim shirt-dresses without any frills are  worth your money.



Stylist’s Secrets to Wear Denim Like a Pro

  1. Jeans with a twinset or a T-shirt plus cardigan are great Casual Friday outfits if your dress code permits.
  2. 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.
    • Depending on your body shape, the right-cut denim jacket is great worn over a summer dress as an alternative to a cardigan
  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. If you aren’t tall like Karlie Kloss don’t go for her Texas tuxedo, i.e. denim everything. See this guide for styling denim-on-denim.
  5. Fool proof combinations to try.
    • 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.
    • Tailored shirts look great even in a denim-on-denim styling.
    • Add classic footwear like pumps, heeled booties, or strappy sandals. Avoid to look like a cowgirl even when you go to Western bar.


Discussed Example: Denim Dress

Denim shirt dresses are great for summer with sandals on weekends and with pumps for a business casual style work look. In the look shown in the photos below, the color scheme is given by the plaid scarf, red, blue, black.


older fashionista looking professional in denim
Liz Claiborne dress (shortened), L.K. Bennett pumps, GNW tights, Hermes enamel bangles, Moda International cardigan (dyed), BCBGMAXARIS belt, and unbranded scarf


fashion blogger Nicole of High Latitude Style looking posh casual in a denim dress
Liz Claiborne denim dress with rolled up sleeves, Kieselstein Cord belt, Liz Claiborne pumps and Chanel bag for a casual, but polished office look.


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 Style or 70s, add a luxury bag and a classic trench coat. Give the outfit an edge with a funky or unexpected pop of color like the 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.


older lady in posh chic Indian ethnic shirt with skinny jeans
Outfit details: Burberry trench coat, Ray Ban sunglasses, Longchamp pliage, ethnic top, Hermes Medor watch, J Brand jeans and Christian Louboutin heels


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.

First let me give you some outfit inspirations.

fashion blogger in Italian jeans and twinset with satchel bag
Oliveo Italian denim bootcut jeans, GG loafers, Prada bag, Brooks Brothers sweater, unbranded long cardigan, malachite and lapis necklace, Kieselstein Cord belt and buckle, Hermes collier de chien bangle


over 50 years old stylist in high rise wide leg pantswearig a denim shirt like a pro
Side view of look described below


over 50 years old woman in shearling motorcycle jacket, plaid pants, denim top, beret, gloves, booties
Great Northwest shirt, Kieselstein Cord belt, Native-made buckle, Pendleton glen-check pants, Coach Chelseas, Anne Klein scarf, Hermes collier de chien bangle, LeatherCoatsEtc beret and gloves, Andrew Marcs shearling, Longchamp bag


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.


example of over 50 years old woman in high-raise denim pants, white shirt
Ralph Lauren silver snake imprint pumps, studded headband, statement belt, amber modernist necklace, Sam Edelman bucket bag, DIY amber bangle, triangle cuff, Hermes collier de chien cuff, quartz earrings, white sun-protective shirt c/o Coolibar and flared jeans c/o Femme Luxe. The white shirt with blue jeans is an all American Classic.


stylist showing how to wear denim like a pro with sunnies, Tee, scarf, gladiator heels
London Jean BFs, Carhartt T-shirt, hand-painted scarf, Studio gladiators, Kieselstein Cord belt and buckle, Ray Ban sunglasses


influencer in distressed jeans, white blazer striped top, pumps
London Jean boyfriends, The Limited T-shirt, linen blazer, structured bag, statement belt, DIY necklace, Hermes collier de chien bangle, Ralph Lauren pumps.


Here some styling inspirations with outerwear for stylish women at any age.


fashion over 40 woman in shearling motorcycle jacket and BF jeans
LeatherCoatsEtc beret and  leather gloves, Ray Ban sunglasses, Andrew Marc shearling, London Jean BFs, YSL bag, Nordstrom Rack scarf, and Clark booties


fashion blogger in denim coat and dress with leo tights
Max Mara coat, Rebecca Collins belt, crocodile briefcase, up-cycled galoshes and dress c/o Covered Perfectly


Next are some denim jackets and shirts outfit inspirations. Wear your jean jacket with a plaid skirt, boots and graphic Tee.

blogger showing how to wear denim like a pro
Pendleton skirt, Great Northwest oversize jacket, graphic T-shirt, and Valentino block heel tall boots


stylist illustrating how to wear denim like a pro
Ray Ban sunglasses, The Limited T-shirt, Juicy Ccouture sandals, Star tailored light-wash jacket, Oliveo leather skirt, LV saddle bag, Hermes collier de chien bangle


Alaskan fashion blogger wearinga denim jacket in street style with leather skirt
Oliveo leather skirt with Levis denim jacket, Kirklander cashmere sweater, Prada bag, Valentino studded pumps and hat


Down-dress a dress with a belted jean jacket as top.

autumn attire with polka dots and jean jacket example how to wear denim like a pro
Great Northwest oversize jacket, Zaful polka-dot dress, statement belt, Michael Kors fall sandals, DIY amber bangle, Hermes collier de chien bangle, wood sports watch c/o Jord, and blue fish clutch c/o Bellorita. The statement necklace picks up the shades of the look,


midlife blogger in lace skirt, sequin patch denim jacket, nude pumps and mirrored sunglasses
StyleWe sequin jean jacket, eShakti lace skirt, Kate Spade basket shoulder bag, Ivanka Trump ankle-strap shoes, Hermes collier de chien bangle, Winkwood sunglasses, unbranded scarf


fashion blog content creator in a plaid dress with denim jacket
Ruby Belle sheath, Great Northwest jacket, Moda International leather motorcycle vest, flower and beads necklace, GNW tights, Harley Davidson booties


In the look above, a sheath serves as skirt under an oversize jacket with leather motorcycle vest. It is an unusual way to layer.


stylist illustrating how to look ageless in a denim jacket, snake print, suede with gemstone hangers
J. Crew snakeprint skirt, Vince Camuto boots, Hermes collier de chien bangle, August Silk top,Festina watch, Judith Leiber belt,Hermes collier de chien bangle, DIY gemstone earrings, tights c/o Hipstik legwear

Debatable Looks: Denim Skirts or Distressed Jeans

General rules are

  • Whether denim skirts look great or not depends on her style, body shape, the skirt’s cut and styling. A tailored cut straight along the tights, dark, above-the-knee version, for instance, creates curves because of the stiff fabric!
  • 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. 😉


Denim Skirt Outfit Ideas

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-and-down the stiffness is not a problem.

If you wear a denim skirt, stay away 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.


nicole wearing a denim skirt like a pro
Oliveo dark denim skirt, Brooks Brothers sweater, Celine bag, L.K. Bennett blue patent leather pumps, DIY belt buckle, unbranded tartan scarf, pantyhose, brooch


influencer in denim skirt, silk shirt, sandals
Jones New York silk top, Oliveo skirt, Anne Klein nude slingback, D&GM sunglasses, statement bag


Try a posh casual ageless monochromatic look.

fashion blogger Nicole of High Latitude Style in Alaskan street style for Thanksgiving
GNW Luxe sweater, Oliveo skirt, Hermes collier de chien, silk scarf, GNW tights, Kieselstein Cord belt and buckle, pendant necklace, golden bangle (gift from my Mom), Steve Madden fall sandals


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.

style blogger in polished distressed jeans attire
Loft BJs, short-sleeve tailored linen blazer, Madonna True or Dare pumps, Tissot watch, Kieselstein Cord belt and buckle, Esprit shoulder-bag, Hermes collier de chien bangle, Brooks Brothers sweater, white jade and black onyx necklace c/o Almo Jewellery


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

Wear distressed jeans with a blazer, knit silk or cashmere sweater and high heels. 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”.

The next outfits illustrates styling distressed boyfriend jeans for a stroll at the mall. The scarf, striped T-shirt, belt and pumps elevate the look. Together the pieces leave no doubt that the distress is on purpose, i.e. due to wear-and-tier.

Style blogger shoing how to wear denim like a pro in striped T-shirt styled with BF jeans

fashion blogger wearing street style with a striped Tee and distressed jeans
T-shirt c/o Marine Layer, Oliveo blazer, Loft distressed BFs, Jaeger tote, Anne Klein sling backs, scarf


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


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


Photos: G. Kramm

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