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

It wouldn’t be too outrageous to say that dressing casual is a daily head scratching dilemma.  Between trying to be comfortable and still look classy  and updated  sometimes it just seems easier to stick with the same old “uniform” you always pull out to wear.

But this mother (JoBee) and her daughters (JoJami/Jannen) nailed it while recently visiting  the Herb Ritts 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:

Herb Ritz Getty Museum

How to Dress Casual

Start with the Shoe: Start with what shoes you are going to wear.  We all need a good pair of comfortable flats to walk in.  A ballet flat can work but the loafer is the newest trend and gives you a little more support.

Janeen Shoes

Start with a cute flat loafer

Print jeans and simple blouse:  Just take a peek at any store window and you will see that printed and colorful jeans are everywhere.  What fun they are to pull out and wear!  The trick here is to keep it simple.  Let the pants shine and the accessories tone them down.  Janeen Full
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.  Janeen Gucci Belt
Hats Off to Accessorizing!  This straw fedora and summer scarf are 2 key pieces to looking fab.  The hat works well to keep 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 not too bulky and made of thin fabric that is lightweight and breezy so it won’t weigh down your outfit. JoBee Hat Scarf
 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
Not too Wild!  These leopard pants are one of my go to pieces.  I can dress them up at night with some leather booties or tone them down for day with brown flats and a jean jacket.  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. Leopard Pants

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Comments, Feedback, & Opinions:

  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.