Casual Dressing Over 40 – What it Is and Isn’t!

If you are over 40 you’ve probably noticed a huge shift over the years to more casual dressing. This is great because it has allowed us to dress in a way that is more relaxed, fun, and often more authentic to who we are. The only problem is, that it’s hard to know what to wear to dress casually because dress code definitions we all grew up with have disappeared.

What exactly is casual dressing and how do you dress casually without wandering into frumpy-ville?  What qualifies as casual women’s clothes over 40?
Here’s a look at what casual dressing means and some ideas for how to dress casually over 40.

Nailing Casual Dressing
The trick, I believe, to dressing casually over 40 is to dress is to wear casual pieces but keep your look classy.

Casual Doesn’t Mean Sloppy

Let’s be honest ladies, where once we could throw on a pair of jeans and a t-shirt and look fabulous when we reach a certain age, a little (or a lot!) more maintenance is required. If we’re not aware of this, or not willing to make a small effort, it can become easy to let ourselves go. Sometimes it sneaks up on us.

Running out to the grocery store? Sweatpants and an old pair of sneakers will do, right? Going to a movie with the hubby? The flip-flops and hoody you’ve been paddling around in the house all day are fine, right? Who’s going to see you in a darkened movie theatre anyhow?
While it sounds good in theory, this laissez-faire attitude is really just a slippery slope to Frumpville. (If you suspect you’re veering down this road, check out my article, 10 Sure Signs You Are Looking Frumpy After 40.)

Casual Does Not Mean Anything-Goes
Just so we’re clear about this, let me say it again and this time repeat after me: “Casual does not mean anything goes.” That’s particularly true when you’re over 40.
Just because you work in a casual office, or just because you’re invited to a casual dinner with friends, you still should give some thought to things like the formality of the venue, the weather, time of year, and especially your personal style and what kind of message you want to convey.
Just because you’re dressing casually, it doesn’t mean you shouldn’t look chic and classy.

Casual Does Not Mean Oversized, Baggy Clothes
Many women equate ‘casual’ with comfortable and then take it a step further and think ‘comfortable’ means loose and baggy. This is particularly true if you carry a little extra weight. (And after 40, who doesn’t? LOL)
I’m here to tell you that hiding under oversized clothes is not doing you any favors. In fact, it is probably making you look bigger, older, and matronly.
If you want to look modern, hip, and fresh, you’re much better off wearing fitted – not tight – casual clothes.

Casual Does Not Mean Living in Denim
I love jeans as much as the next gal but please know that denim is not your only casual outfit option. A cute pair of cotton chinos or a pretty knit dress are both examples of non-denim casual outfits. Mix it up a bit.

Casual Does Not Mean Juvenile
We sometimes tend to equate casual with the way kids dress. While jeans, t-shirts, and sneakers can and often do figure into the casual wardrobe of an over-40 woman, our version should be chicer than what most 14-year-olds are wearing. Sneakers are great but consider a cute slip-on version in a pretty shade of blush instead of the gym shoes your teenagers might wear.

Casual Does Not Mean Out-of-Touch with the Trends
Fashion is always evolving – even casual fashions – and if you intend to look ‘with-it’, modern and vibrant – what I like to call Age-Amazing – then you should keep up with it.
I’m not talking about being an overly-trendy fashion victim. Even just being aware of the trends and picking and choosing the ones that are right for your body, your lifestyle, and your personal style will go a long way in helping you tweak your chic.

Dear Deborah,

I am a 49-year-old woman who lives in the Northeast, and while I do dress up occasionally for dinner or evening out, 95% of the time I need to be dressed for getting in and out of a car, easily; for walking to and from places on a variety of sidewalks, and for a very casual everyday kind of life.

I’m finding myself at a perimenopausal standstill!  I have run out of creativity, and I am sliding down the slippery slope of jeans, colorful t-shirts, fleece, and turtlenecks.  Yuck!

I also have to wear comfortable shoes and boots to fit my aging feet.  How do women like myself, who live casual lifestyles full of activity and creativity, help themselves to feel, and look, attractive, year-round?

Thank you again, Lori

Hi Lori,

Your letter was so heartfelt and your question so common! Many women see their lifestyle change once they are past 40. Casual wear becomes something they wear a lot! Here are a few tips to get you started:

1. Do you have a Cute Faux Fur Vest?

Many women don’t think about buying a vest to dress up their casual wardrobe, but I bet if you do you will be hooked. faux fur vests are very popular at the moment and look great at any age.

Wear one with jeans, a shirt, and some really cute books, and you have a showstopper casual outfit.

2. Have you tried a Sweater Dress?

A sweater dress with some patterned tights and knee-high or over-the-knee boots works.  Don’t feel like you have to wear pants all time. Why not snuggle into a sweater dress and feel more feminine and a little funkier!

3. Try a Dash of Color

Lord knows we wear far too much black after 40 and it’s not always so flattering. All those years of black can really drag a woman down now that our skin is not as vibrant as it once was. Read all about ABD, and you will know what I’m talking about.  It’s time to put some color into your casual wardrobe. A coat is a great place to start.

4. Have you considered Leggings?

You say you want to be comfy. Stretchy leggings are the most comfortable thing you can wear. The key to looking good in them is to make sure they cover your bottom and more. Buy some thick black leggings and pair them with a long loose sweater like this. Add some jewelry and glam accessories, and you have a chic, casual look.