Stylist’s secrets how to wear denim like a pro

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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.

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

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

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

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
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)

 Levis denim jacket with eShakti lace pencil skirt, Festina watch, and Prada bag for a posh Casual Friday look
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

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)

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

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

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.

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.

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. 😉

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.

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.

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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.

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Photos: G. Kramm

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