Stylist’s secrets how to wear denim like a pro
  1. Can you wear denim in midlife and beyond?
    • Advanced styling tips for denim over 40
  2. Stylist’s secrets on wearing denim
    • Inspirations how to wear a denim skirt
    • Inspirations how to style a denim jacket
    • Inspirations how to wear jeans
    • Inspiration how to style a denim shirt over 40
    • Discussed example: Denim dress
    • Discussed example: Disstressed jeans
      • How to make distressed BF look great for Casual Friday
    • Discussed example: Skinny jeans
  3. Keeping in touch

Disclosure: There are affiliate links in this post.

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, trying not at all. Going beyond the basics in wearing denim over 40 sounds like to balance on the sharp side of a carving knife. Denim is associated with casual and weekend and can go easy frumpy or looking like wearing a uniform.

Advanced styling tips for denim over 40

In an earlier post of this Ageless Style series, I gave tips what to look for when seeking for an ageless outfit in denim. Today’s post expands on those tips by providing tips how to style denim like a pro.

First let me give you some outfit inspirations.
fashion blogger in Italian jeans and twinset with satchel bag

fashion book author in bootcut jeans, faux twinset and loafers
Oliveo mid rise, Italian denim bootcut jeans, GG loafers, Prada bag, Brooks Brothers sweater, unbranded long cardigan, statement malachite and lapis necklace, Kieselstein Cord belt and buckle and Hermes collier de chien bangle (all own)

over 50 years old stylist in high rise wide leg pants with denim shirt

style blogger in pants and denim press button shirt with belt and scarf

over 50 years old woman in shearling motorcycle jacket, plaid pants, denim top, beret, gloves, booties
Great Northwest denim shirt, Kieselstein Cord belt, native buckle, Pendleton glen check pants, Coach Chelseas, Anne Klein scarf, Hermes collier de chien bangle, LeatherCoatsEtc beret and gloves, Andrew Marcs shearling motorcycle jacket, Kate Moss for Longchamp bag and statement studs (all own)

Stylist’s secrets on wearing denim

  1. Recall to stay away from the extremes like a superwide bell-shape or super-distressed. Both look sort of ridiculous at any age. A straight cut is a classic, but pairing shoes with it is much more difficult than for skinnies, or a slight bootcut.
    1. 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.
    2. A turtleneck sweater with jeans and blazer also falls in this category.
  2. Many stylists advise against wearing a denim skirt over 40 due to the stiffness of the fabric. However, when the cut is to the advantage of providing shape to a straight-up-and-down body and the skirt is above the knee it can work to your favor. Not sure what body type you have? Detect your body shape type with this free online quiz.
    1. If you wear a denim skirt, stay out of dressing like a cowgirl, i.e. don’t add a plaid shirt plus fringe leather jacket and cowboy boots and a hat unless you go to a western bar or festival. You would look otherwise like Rosie in Disguise.
    2. Style the denim skirt like you would style 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.
  3. Denim jackets are a nice way to style a dress down. Click To Tweet
    1. Try a denim jacket as an alternative to a cardigan.
    2. Belt your denim jacket and/or wear it under a vest.
    3. Pair a denim jacket with a romantic dress or skirt, a lace dress or sequin skirt for an unexpected going out look.
  4. Denim-on-denim looks best with two different washes, but same texture. Click To Tweet Think one of the denim-on-denim pieces just has been washed over and over again while the other hasn’t.
    1. If you aren’t tall like Karlie Kloss don’t go for her Texas tuxedo, i.e. denim everything.
    2. 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.
    3. Try a denim piece with a white (or colored) denim piece.

Inspirations how to wear a denim skirt

mature woman looking great in a denim skirt Weekend look with dark-wash Oliveo denim skirt with a striped Jeanne & Pierre sweater, GNW tights, Prada bag, statement belt, scarf and Puma silver sneakers (all own). The color and posh style of the sneakers plus the accessories (scarf, statement belt) give the casual outfit a stylish look
midlife woman looking great in a denim weekend outfit Classic American weekend outfit with straight Oliveo denim skirt, Kieselstein Cord belt, H-buckle, Anne Klein T-strap pumps, statement necklace, Hermes collier de chien bangles (all own), and a striped T-shirt c/o Marine Layer

Inspirations how to style a denim jacket

stylist in denim jacket Lace dress with Levis denim jacket, Harley Davidson booties,  three string pearl necklace, and Hermes collier de chien  belt (all own) for an unexpected going out look
over 50 fashion blogger in a white denim jacket over sheath dress Styling down an Elie Tahari abstract floral print sheath dress with a Fossil white denim jacket for Casual Friday. The red Gloria Vanderbilt pumps, Chanel belt, Ray Ban sunglasses and fuchsia 3.1 Phillip Lim tote tie the look together (all own)
influencer wearing a lace pencil skirt with denim Levis denim jacket with eShakti lace pencil skirt, Festina watch, and Prada bag for a posh Casual Friday look
fashion blog content creator in a plaid dress with denim jacket Styling a Ruby Belle plaid sheath dress down for Casual Friday with a Levis denim jacket worn as a top under a VS leather vest, GNW tight, dagwood flower and beads statement necklace, Festina watch, and Harley Davidson motorcycle booties (all own)

Inspirations how to wear jeans

 #styleover50 mature woman in boyfriend jeans London Jean boyfriend jeans styled up for Casual Friday with a striped T-shirt, linen blazer, structured bag, statement belt, DIY necklace, Hermes collier de chien bangle, and Ralph Lauren silver pumps (all own)
#fashionover50 mature woman wearing skinnies J Brand skinnies styled for a comfy, but polished weekend winter look with Brooks Brothers mock turtleneck sweater, pearls (all own), and a light trench coat worn as jacket c/o Lookbook Store.

Inspiration how to style a denim shirt over 40

#fashionover40 woman in denim shirt Great Northwest denim shirt styled as a jacket with Studio Sierra leather skirt and jacket, GNW tight, Harley Davidson booties, and GNW cardigan worn as a top (all own) for a warm winter Casual Friday look
#styleover50 woman wearing a denim shirt under a dress Great Northwest denim shirt worn under a GAP LBD with DIY statement belt, GNW polka dot tights, Hermes collier de chien bangle, and L.K. Bennett pumps (all own) for an office-appropriate look

How do you style your denim? Do you wear denim-on-denim? What’s your favorite outfit with this fabric? I am curious.

Discussed example: Denim dress

In the look shown in the photos below, the color scheme is given by the plaid scarf, red, blue, black.
mature woman in denim dress

older fashionista looking professional in denim
Liz Claiborne denim dress (shortened), L.K. Bennett navy patent leather pumps, GNW black tights, Hermes enamel bangles, Moda International cardigan dyed red, BCBG belt, and unbranded red-black-blue plaid scarf (all own)

Discussed 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 the distressed jeans shown in the photos below I think 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. About a year ago, my best friend bought a pair of sweatpants with a distressed print. That made me even more to want my own pair of distressed BF jeans.

midlife fashion blogger looking posh chic in distressed BF jeans

mature style blogger in polished style with distressed jeans
Outfit details: Loft distressed BJ jeans, unbranded white short sleeve tailored linen blazer, Madonna True or Dare floral patent leather pumps, Tissot watch, Kieselstein Cord belt and buckle, vintage Esprit shoulder bag, Hermes collier de chien bangle, Brooks Brothers silk cashmere knit sweater (all own) and  white jade and black onyx necklace c/o Almo Jewellery

When I saw these sweatpants the last time, I mentioned it. My best friend was like “do you really want to pay more money for a pair of jeans that is already broken?” “Sure, the distress is another step in the production process. That’s why they cost more.” “Right, but they are ugly.” “Then why did you buy sweat pants with a distress print?” “They are not broken.” “But have an ugly print?” We both LOL. 🙂

After doing some insomniac online shopping I got these. When I wore them the first time, my best friend pointed at the distress and said “yack”, but loved them in the overall outfit/look so much to take not only one photo, but one from from all angles. 😉

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

Alway experiment with new things you like. Some items that are first a trend – like distressed BF jeans –  become later a classic and when worn with classics they just add the little twist that keeps a classic look from being boring. Classic with a twist. The distress as the surprise.

How to make distressed BF look great for Casual Friday

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

Discussed example: Skinny jeans

In this example, I paired 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 or 70s, I added a classic trench coat, and a luxury bag. To give the outfit a little edge and a little more color I added my neon yellow pumps. Always repeat a color at least twice in an outfit like in this example neon yellow and sunflower yellow.

mature stylist in an outfit with ethnic shirt styled in a western way with skinnies and pumps

older lady in posh chic Indian ethnic shirt with jeans

old woman in a casual posh jean outfit
Outfit details: Burberry trench coat, Ray Ban sunglasses, sunflower yellow Longchamp pliage de cuir bag, unbranded white Indian ethnic embroidered top, Hermes Medor watch, J Brand jeans, and neon yellow Christian Louboutin heels (all own)

When you like any of these outfit inspirations, it would help me if you pinned them to your own Pinterest board. It’s a great way that your friends, family, and others can see them too.

When you liked this post share it with your friends by tweeting them: Read these great tips on how to look awesome in denim over 40. #agelessstyle #fashionover40 Click To Tweet.

Are you registered for my email notification to let you know about new posts? I’d highly appreciate it if you take the time to sign up and ask your friends to sign up too!!

What item do you love, but never dared to buy? What is holding you back? Let me know your dressing challenges by email so I can help you.

When you are interested in reviews of the newest trends, and fashion and how to turn them into personal style, to look to your best in midlife, subscribe to High Latitude Style. Deep inside you know when I can do it, you can do it too.

Photos: G. Kramm

© 2013-2020 Nicole Mölders | All rights reserved