How to Dress Stylish and Comfortable When You’re Over 40 and Beyond

I think you’d agree that figuring out how to dress casual is a daily head scratching dilemma.  Between trying to be comfortable and still look classy and updated, it  sometimes it just seems easier to stick with the same old “uniform” you always pull out to wear.

How to dress professionally and stylish

How to dress more stylish


But this mother (JoBee) and her daughters (JoJami/Jannen) put some effort into it and nailed casual dressing when they went to visit the Herb Ritts fashion photography exhibit at the beautiful Getty museum.  It was an afternoon filled with lots of walking so they all opted to wear flats.  The big trick was how to throw some pizzazz into the mix.  Here’s a breakdown of  dressing ideas they used:

Start with the Pants 

Take a peek at any store window and you will see that print jeans are everywhere.  The trick here is to keep it simple. Let the pants shine and the accessories tone them down.

JoBee has on metallic blue jeans that are really sexy at night with a black top and boots, but for day she can have a little fun with adding the colorful jacket.  JoJami loves her leopard print pants that she dresses up at night with sexy booties and Janeen adds more gltiz at night when she wears these patterned silver jeans, but by day they pare it down.


Print jeans and simple blouse:  
The best way to show off your patterned jeans is with a plain shirt or silky blouse.

Print jeans and silky blouse for how to dress stylish at 40

Print jeans and simple blouse

If you tuck in you will want a neutral colored belt:  This belt adds just the perfect touch to finishing off Janeen’s outfit.  Having a classic leather belt is one item that can instantly jazz up an outfit.

classic leather belt

Classic leather belt for women

Hats Off to Accessorizing!  
This fedora keeps the sun off your skin and can be worn if you’re having a bad hair day, too!  If you opt for a scarf, make sure it’s thin, breezy and not too bulky so it won’t weigh down your outfit.

How to dress comfortable and stylish

How to dress comfortable and stylish

Summer Straw Tote:  
This tote is lightweight and will go with any casual outfit.  You could wear just this one bag all summer and do just fine.

JoBee Straw Handbag - How to Dress Stylish at 40

How to dress comfortable and stylish

Be comfy:
You are walking a lot. Loafers are often more comfortable than ballet flats because they are a little wider at the toe.

JoBee loafters - how to dress professionally and stylish

Comfortable shoes for women

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  1. JoBee looks amazing. Well, all three of you look great, to be honest. Each outfit really works. Thanks for the tips.

  2. Classy printed jeans–could you share the brand? Most of the ones I’ve found in my area are a little too bold or too floral for my current tastes. Thanks

  3. Woohoo! Look at JoBee in those skinny jeans!

  4. margaret says:

    Please let us know who makes the beautiful loafers. I too have researched and found nothing like these.

  5. I think these ladies look great… BUT, its much easier to dress like this when you’re lovely and slim like them too! There are a lot of us. that whilst not overweight are carrying a few extra pounds and not game to go down the skinny pant path!

    • Hi Annette, I do understand that not everyone is super slim. That is why most of the tips that I feature on Fabulous After 40 are meant for women over 40 and can be used by any one of any size. I like to use myself when I can. If you go to my FACEBOOK page you will see women of all shapes and sizes. Thanks for sharing your comment.

  6. Ladies – you rock! I love a printed pant whether it be jeans or otherwise that you can dress up or dress down to suit whatever the occasion. JoBee cannot possibly be your mother! I want to see some i.d. please.

  7. Thanks for the great tips. I would love know where Janeen got those gorgeous loafers. I got online and can’t find anything like them.