How to look great in denim over 40

Jeans are a casual wardrobe essential

Today jeans are an essential of the every day 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.

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 how to wear jeans in ageless style. Here is what I found what works and what doesn’t.

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. Denim in bright colors or white look great too at any age.
• Tailored denim shirts look great even in a denim on denim
• When wearing denim on denim always go with distinct different shades and accessorize with classic items like pumps, heeled booties, or strappy sandals. Avoid to look like a cowgirl even when you go to a western-style Night Club.
• Jeans with a twinset or a T-shirt plus cardigan are great for Casual Friday if your dress code permits denim.
• Soft denim shirt-dresses without any frills are great for summer with sandals and a belt for the weekend and – if the dress code allows – 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

Examples of great denim looks for women in midlife

Here some visual denim styling inspirations for fashion over 40.

This denim jacket replaces a blazer in the Casual Friday office look. The pumps, sweater, structured bag and pants make the look business casual. The color palette sticks to neutrals
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 fall Outfit with 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 look

Example of outfit with tailored jacket worn with striped T-shirt, white leather skirt, saddle bag and plateau sandals for a Sunday brunch
Example of styling boyfriend jeans for a business casual office look by adding a blazer, a striped button-down shirt, white pumps, pearls, and a structured bag Example of a fall weekend outfit with skinnies, a leather baseball jacket, booties (all own) and striped T-shirt c/o Marine Layer

Debatable looks

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. A main argument against denim skirts is their stiffness. I agree that they may be stiff depending on the weight of the fabric, but I disagree that stiffness means a bad style/look.

My 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, looks great on me. It gives me some curves because the fabric is stiff! The cut fits my sleek style.
• If you go for distressed jeans, make sure it is obvious that you bought them that way, i.e. that they are not a leftover from your time back then in college. 😉

Outfit inspirations

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

Example of styling distressed boyfriend jeans for a stroll at the mall or Casual Friday. The silk scarf, classic striped T-shirt c/o Marine Layer, own statement belt and Anne Klein slingback pumps elevate the look and leave no doubt that the distress is on purpose, i.e. not caused by wear

When you liked the outfit recipes 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

What is your opinion on denim skirts? What do you think about distressed jeans? Yay or Nay? What are your style challenges when it comes to wearing denim? Let me know so I can help you.

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You may be also interested in these posts on Ageless Style in Plaid, and Global Inspirations.

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Photos: G. Kramm

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