Where to Find Solutions to Your Style Challenges over 40
BB Dakota dress with crafted gem stone animal necklace, Jeanne Pierre sweater, GNW tights, Steve Madden Mary Janes (all own) at the Chena River in Fairbanks, Alaska

The goal of this post is to lead you to the available guides that address various style challenges of women over 40.

  1. How to Master the Challenge of Turning Fashion into Style
  2. The Mixing Prints/Pattern Trends Is a Thread
  3. Over-The-Knee Boots
  4. Leather and Make-up
  5. Wrapping up

Disclosure: There are affiliate links in this post.

How To Master The Challenge of Turning Fashion Into Style

There are many style and fashion challenges out there for us women over 40. Thus, I asked my readers last Wednesday in my Ageless Style series what they want to see addressed. Many thanks to all of you who made suggestions! They are all very appreciated. Here I will point you to posts that provide solutions to your questions on how to solve these thread.  🙂


#fashionover40 #fashionover50 Style challenges for 40+ woman in T-shirt and denim jacket
Eddie Bauer tweed skirt with Levis denim jacket, Hermes Medor watch, Hermes collier de chien bangle, Steve Madden lace-up booties, Camel bag, and The Limited striped T-shirt (all own)


The challenges all have in common to turn fashion trends into style. All to often the trendy items look plain trashy on a mature woman. The reason? Bad craftsmanship to keep the items cheap. The solution:

To turn fashion into style go for trends that you can do with high quality items. #fashionover40 Click To Tweet
#fashionover40 #fashionover50 accessories are key
Zoom-in on the Camel bag and Hermes Medor watch. Modern accessories are key

Trends That Are a Second Time Around Are Challenging

Trends in general, and in particular from past decades like the 70s, for instance, came in high first. Quite understandable as we don’t want to look like a fashion victim and/or stuck in time or an old-fashioned style rut. 😉

Get informed how trends that are a second time around are styled today. #fashionover40 Click To Tweet

fashion blogger in tweed skirt and denim jacket

stylist in Casual fall outfit
Outfit details: The Limited striped T-shirt, Eddie Bauer tweed skirt, Levis boxy denim jacket, Hermes collier de chien bangle, vintage Camel bag and Steve Madden fall booties (all own)

The Over-The-Knee Boots

Another great issue is over-the-knee boots. They are great in winter to keep the knees warm in cold climates. However, we don’t want to get into “Pretty Woman” territory despite we all have loved Julia Roberts wearing them in the movie, and some of us even had a tuned-down street style flat version back then. But how can we wear them and look sophisticated now that we are over 40? The solution in a nutshell:

Go for high quality leather OTKboots with sturdy heels and a classic design. #fashionover40 Click To Tweet

You can find a guide how to wear over-the-knee boots over 40 at this link.


Dior over-the-knee boots over 40
Dior Over-the-knee boots (own)

The Mixing Prints/Pattern Trends Is a Thread

Mixing prints/pattern came in third immediately followed by make up and leather. These topics are hot and one better gets them right. Mixing prints done right look incredible stylish; but done wrong, it looks ridiculous at our age. You can find a guide on stylishly mixing prints and patterns at the link.

stylist in mixed prints and pattern over 40
Kate Moss for Longchamp satchel, Christian Louboutin pumps, Kieselstein Cord belt and buckle, GNW paisley print cardigan worn as top (all own), and faux wrap dress c/o HSN

Leather and Make-up

Leather is an expensive investment. You can learn what to look for when shopping for leather clothes in this guide.

Over 40, makeup should be like the icing on the cake. Click To Tweet

We don’t want to look painted. 😉 See this post on how to get a barely there makeup.

Wrapping Up

These challenges are addressed in the linked posts. Tomorrow’s post addresses how to master fall’s tricky 70s trend.

Don’t let your outfit be a random thing. Wear the right look in every situation by looking up what to wear when in How to Dress for Success in Midlife. Buy the book now.

What are your style challenges? What do you think is the hardest/toughest thing for women our age? You can still submit your style challenge that you want to see covered in Ageless Style. Fall relevant topics addressed in guides by Ageless Style in the past were, for instance,

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Photos: G. Kramm

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