How to Wear Denim Like a Pro

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.

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.

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 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

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.

Try an all American Classic look.

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

Explained Example: Skinny Jeans

The example below 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.

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.

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

The look above is an unusual way to layer 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 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.

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.

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.

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 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.

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”.

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.

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. See this guide for styling denim-on-denim.

Expert 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

You may be also interested in my styling guides on Plaid, or how to look ageless in the Global trend.

Photos: G. Kramm

© 2013-2023 Nicole Mölders | All rights reserved