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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. Learn how to wear denim like a pro at any age, and get inspired to create sophisticated business casual style, Casual Friday, weekend and date night outfits.

 

Contents
  1. Jeans Are a Casual Wardrobe Essential
  2. Tips to Buy the Right Denim for You
  3. Stylist’s Secrets How to Wear Denim Like a Pro
    • What Looks Great with Jeans?
    • Explained example: Skinny jeans
    • Discussed example: Denim Dress
    • How to Style a Jean Jacket
    • Denim Shirt Outfit Ideas to Try
    • What Goes with a Denim Coat?
    • Colored and White Denim
  4. Debatable looks: Denim Skirts or Distressed Jeans
    • Denim Skirt Outfit Ideas
    • Explained example: Disstressed Jeans
    • Texas or Canadian Tuxedo
  5. Can you wear denim in midlife and beyond?
    • Advanced styling tips for denim over 40
  6. What Does Not Work?

Disclosure: This post contains affiliate links.

 

Jeans Are a Casual Wardrobe Essential

Today jeans are an everyday wardrobe essential 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 with a black blazer and black top are a NYC standard uniform. Denim is a staple.

 

 

flyer how to wear denim like a pro showing gray hair woman in jean 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 pants and jeans, right? Why should we give up on them now? We were the trendsetters back then. Let’s become the trendsetters how to wear denim over 50!

 

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

 

 

 

influencer lobbing how to wear denim like a pro
Levi’s 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

To wear denim like a pro fit is key. In the case of great fit for jeans, think Jane Birkin in the 1970s for flared jeans, strive for a fit like Brook Shields in the Calvin Klein ads in the 1980s, or Cindy Crawford in her straight cut in the 1990s. Therefore, have a photo of you bum taken by the salesperson. If you find a brand and cut that flatters you, stay with it until they change the cut.

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, style the jeans like Marilyn Monroe did.

  • 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.
  • Stay out of mommy jeans land! Even straight jeans should fit tight thru the waist, hip and at the bum.
  • Always go for a dark wash.
  • Soft denim shirt-dresses without any frills are worth your money.

 

 

Stylist’s Secrets How to Wear Denim Like a Pro

What Looks Great with Jeans?

  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 super-wide 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.
  3. 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.
  4. A turtleneck sweater with jeans and blazer also falls in this category.

 

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

 

Try a white shirt with blue jeans. It is an all American Classic.

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.

 

Scarves are perfect to up the style factor of an outfit when you know how to style with scarves. Use the colors of the scarf to tie the look together. In the example below, the scarf repeats the colors of the sandals or vice versa.

 

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 BF 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.

 

mature woman showing how to wear denim with a shearling motorcycle jacket
LeatherCoatsEtc beret and  leather gloves, Ray Ban sunglasses, Andrew Marc shearling, London Jean BFs, YSL bag, Nordstrom Rack scarf, and Clark booties.

 

Explained Example: Skinny Jeans

The example shown below pairs skinny jeans with an ethnic shirt for a western vibe Casual Friday work outfit. To keep the look from going Bohemian Style or 1970s, 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.

 

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

 

 

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

 

 

How to Style a Jean Jacket?

  1. Denim jackets are a nice way to style a dress down.
  2. Try a denim jacket as an alternative to a cardigan. More on what to wear with a denim jacket.
  3. Belt your denim jacket.
  4. Wear it under a vest.
  5. Pair a denim jacket with a romantic style dress, skirt, lace dress or sequin skirt for an unexpected going out look.

 

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 in summer
Ray Ban sunglasses, The Limited T-shirt, Juicy Couture sandals, Star tailored light-wash jacket, Oliveo leather skirt, LV saddle bag, Hermes collier de chien bangle

 

Alaskan fashion blogger wearing a denim jacket in street style with leather skirt
Oliveo leather skirt with Levis denim jacket, Kirklander 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 illustrating how to wear a denim jacket with a plaid dress
Ruby Belle sheath, Great Northwest jacket, Moda International leather motorcycle vest, flower and beads necklace, GNW tights, Harley Davidson booties

 

In the look above, the sheath serves as skirt under an oversized 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 snake print 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

 

 

Denim Shirt Outfit Ideas to Try

Fool proof combinations to try with a jean shirt:

  1. 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.
  2. Try a denim piece with a white (or colored) denim piece. More on denim on denim.
  3. Tailored shirts look great even in a denim-on-denim styling.
  4. Add classic footwear like pumps, heeled booties, or strappy sandals. Avoid to look like a cowgirl even when you go to Western bar.

 

over 50 years old stylist in high rise wide leg pants wearing 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

 

 

 

Discussed Example: Denim Dress

Denim shirt dresses are great for summer with sandals on weekends and with pumps for a business casual style outfit. In the photos below, the plaid scarf provides the color scheme (red, blue, black). More on bold fashion color combinations.

 

older fashionista looking professional in a denim dress
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.

 

 

What Goes with a Denim Coat?

There is no difference between how to wear a denim coat and another coat. The length and what shows from your outfit are key. For more information see how to create an ageless capsule coat wardrobe.  When it comes to accessorizing see these styling inspirations with outerwear.

 

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

 

 

Colored and White Denim

The fabric looks great too in bright colors or white at any age. However, be aware that colored denim fails to get the comfort of jeans. This fact is true also for white denim because the fibers (cotton or hemp) natural color is greige.

Learn more on what to wear with white denim.

 

 

Debatable Looks: Denim Skirts or Distressed Jeans

General rules how to wear denim like a pro when it comes to these statement pieces 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. Avoid a plaid shirt plus fringe leather jacket, cowboy boots, and hat look unless you go to a western bar, Wild West festival or outdoor concert. You would look otherwise like Rosie in Disguise.

Style a 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 ilusstrating how to wear a denim skirt like a pro with a silk shirt, sandals
Jones New York silk top, Oliveo skirt, Anne Klein nude sling back, 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

You surely have read the countless memos in various fashion magazines, newspapers, and style books:

No distressed jeans after 40.

But who of us didn’t love the distressed BF jeans when Kate Holmes set that trend. Here in one sentence, how to wear denim like a pro:

Style distressed jeans with luxury items for a classic with a twist and stir clearly away from anything “frumpy”.

 

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 distressed jeans with a tailored, high quality blazer, knit silk or cashmere sweater and high heels. Accessorize with a statement necklace like in the look above, and add a belt and leather high heels to add polish.

The next outfits illustrates how to style distressed boyfriend jeans for a stroll at the mall. The scarf, striped T-shirt, belt and pumps elevate the look. Therefore, the outfit leaves no doubt that the distress is style.

 

Style blogger shoing how to wear denim like a pro in striped T-shirt styled with BF jeans
As look below, but without blazer

 

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

 

 

Texas or Canadian Tuxedo

If you aren’t tall like Karlie Kloss don’t go for her Texas tuxedo, i.e. denim everything. However, mixing colored and jean denim or two denim pieces is worth a try. See this guide for styling denim-on-denim.

 

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

 

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. Frump alert!
  • 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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