You are currently viewing How to 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. 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.



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.


midlife woman in indigo coverup yellow leather skirt burgundy top brown shoes and bag printed neckerchief
Dior neckerchief, Great Northwest coverup, Longchamp bag, Quince sweater, Hipstik pantyhose, Tahari pumps, watch c/o Nordgreen. The neckerchief’s print ties the colors of the OOTD together.



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.

Chose the right pants for your body shape. 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 between sizes
  • Make the real life test. Sit down.  When a gap shows up in the back or the top of your thongs shows like a diving whale’s tail, the fit is not right.
  • When you are short-waisted go for low-raise just above the hip bone, while long-waisted women look better in mid-raise or high-waisted cuts.
  • Straight jeans should fit tight thru the waist, hip, and at the bum.
  • Go for a dark wash.
  • Soft denim shirt-dresses without frills are worth your money.



Stylist’s Secrets How to Wear Denim Like a Pro

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. Get 15% off with my discount code HLSTYLE.


What Looks Great with Jeans?

  1. Jeans with a twinset or a T-shirt plus cardigan are great Casual Friday outfits.
  2. 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. Paired with a white shirt is an American Classic.
  4. Try a turtleneck sweater with jeans and blazer.
  5. Jean pants look great with Plaid.


stylist showing how to wear jeans in summer and fall
From left to right jean trousers outfit ideas: With twinset. 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. As American Classic. 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. Casual Friday outfit. London Jean boyfriends, The Limited T-shirt, linen blazer, structured bag, statement belt, DIY necklace, Hermes collier de chien bangle, Ralph Lauren pumps. Casual weekend look. London Jean BFs, Carhartt T-shirt, hand-painted scarf, Studio gladiators, Kieselstein Cord belt and buckle, Ray Ban sunglasses.


Tip: Scarves are perfect to tie an outfit together repeating the colors of the pieces.



Explained Example: Skinny Jeans

The example in the middle pairs skinny jeans with an ethnic shirt. To keep the look from going Bohemian Style or 1970s, add a luxury bag and a classic trench coat. A funky or unexpected pop of color like the neon-yellow pumps creates a twist.


outerwear examples with indigo dyed denim
Left: LeatherCoatsEtc beret and  leather gloves, Ray Ban sunglasses, Andrew Marc shearling, London Jean BFs, YSL bag, Nordstrom Rack scarf, and Clark booties. Middle: Burberry trench coat, Ray Ban sunglasses, Longchamp bag, ethnic top, Hermes Medor watch, J Brand jeans, and Christian Louboutin heels. Right: Max Mara coat, Rebecca Collins belt, crocodile briefcase, up-cycled galoshes and Covered Perfectly dress.



Tip: 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 wearing a denim jacket as an alternative to a cardigan.
  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.



style blogger featuring how to wear a denim jacket with skirts
Left: Pendleton skirt, Great Northwest oversize jacket, graphic T-shirt, and Valentino boots. Middle: Ray Ban sunglasses, The Limited T-shirt, Juicy Couture sandals, Star tailored light-wash jacket, Oliveo leather skirt, LV bag, Hermes collier de chien bangle. Right: Oliveo skirt, Levis denim jacket, Kirklander sweater, Prada bag, Valentino studded pumps, and hat.



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


style book author illustrating how to look ageless in a denim jacket
Left: StyleWe sequin jean jacket, eShakti skirt, Kate Spade basket, Ivanka Trump ankle-strap shoes, Hermes collier de chien bangle, Winkwood sunglasses, unbranded scarf. Right: 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.


Tip: Wear a belted jean jacket as top.


dress and sheath with jean jacket outfit ideas
Left: Great Northwest oversize jacket, Zaful polka-dot dress, statement belt, Michael Kors sandals, DIY bangle, Hermes collier de chien bangle, wood watch c/o Jord, and clutch c/o Bellorita. The statement necklace picks up the shades of the look. Right: Ruby Belle sheath, Great Northwest jacket, Moda International vest, gemstone necklace, GNW tights, Harley Davidson booties.


Tip: Wear a sheath as skirt under an oversized jacket with leather vest.



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 jean denim with white or colored denim.
  3. Tailored shirts look great even in a denim-on-denim styling.
  4. Add classic footwear like pumps, heeled booties, or strappy sandals.


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 (red, blue, black) bold fashion color scheme.


how to style a denim shirt dress for work in winter and summer
Liz Claiborne dress (shortened). Left: L.K. Bennett pumps, GNW tights, Hermes enamel bangles, Moda International cardigan (dyed), BCBGMAXARIS belt, and unbranded scarf. Right: Dress sleeves rolled up, Kieselstein Cord belt, Liz Claiborne pumps and Chanel bag for a casual, 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 an ageless capsule coat wardrobe. Furthermore, how to accessorize outerwear remains the same.



Colored and White Denim Facts to Know

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 wearing white denim because the fibers (cotton, flax, hemp, or blends thereof) natural color is greige. The fiber or raw material is just bleached to achieve an even color.



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 your 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.

When wearing a denim skirt, avoid dressing like a cowgirl. Don’t add a plaid shirt, fringe leather jacket, cowboy boots, and hat unless you go to a western bar, Wild West festival or outdoor concert.

Style a denim skirt like a corduroy skirt with a striped Tee or polo shirt. Or like a black pencil skirt with a white button-down shirt and black or nude pumps.


denim skirt outfit ideas
Oliveo dark denim skirt. Left: Brooks Brothers sweater, Celine bag, L.K. Bennett blue patent leather pumps, DIY belt buckle, unbranded tartan scarf, pantyhose, brooch. Middle: Jones New York silk top, Anne Klein nude sling back, D&GM sunglasses, statement bag. Right: GNW Luxe sweater, 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.


Trend alert: Try a posh casual ageless monochromatic look.



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 book author showing what to wear with distressed jeans
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.


Tip: Wear distressed jeans with a tailored, high quality blazer, knit silk or cashmere sweater. Accessorize with a statement necklace, belt and leather high heels to add polish.



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. This outfit illustrates how to style distressed boyfriend jeans for a stroll at the mall. The scarf, striped T-shirt, belt and pumps elevate the look.



Texas or Canadian Tuxedo

If you aren’t tall like Karlie Kloss don’t go for her denim everything. However, mixing colored and jean denim or two denim pieces is worth a try.


Tip: Wear what looks great on you and forget about the rest.


What Does Not Work?

  • Cut-offs. 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


Photos: G. Kramm

© 2013-2023 Nicole Mölders | All rights reserved

What do you think?

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This Post Has One Comment

  1. Great article! I hadn’t known (why should I-?) about the trick of photographing one’s bum to find jeans to match, but it makes sense. How the bum was shaped was a big thing back in the 1970’s.