How to Dress Casual but Stylish Over 40 {VIDEO}

Wondering how to dress for your relaxed lifestyle without looking like a frump?

Watch this video to learn 3 ways to dress casual, but classy after 40.

Deborah Boland

Deborah: Maybe you realize it’s time to trade in the yoga pants or faded jeans and loose t-shirt that you’ve schlep around in for something else. But what do you replace them with?

Tip #1: Colored Jeans are a Fabulous choice

They’ve become mainstream and you can get them in any color under the sun. Now if you are worried about standing out too much in colored jeans, don’t be.

All you need to do is wear your colored jeans with a neutral colored top or blouse to tone things down a bit. Add some flats or sandals or even a cute pump if you want a dressier feel, and you’ve got a fresh new look.

Jumpstart Your Style over 40

Another way to combine classy and casual is to wear a long top with leggings. Look for a top or tunic that has some interesting detail and that is long enough to cover your bottom. Sometimes a short dress can even double as a top. Wear your tops with some dark leggings, fun jewelry, and wedges, flats or low heeled boots if you want a modern and very comfy outfit.

Tip #3: Get Yourself a Great Fitted Jacket.

Finally, I hope you own at least one great fitted jacket in a fabulous color. The boyfriend jacket with its rolled up sleeves is a relaxed but polished look.

A fine leather jacket is also a really wonderful piece  to own and adds a nice touch of sexy. Whatever jacket you choose, make sure it nips in at the waist because a defined waist makes you more youthful and stylish over 40.

For more great tips on How to Dress with Style, pick up a copy of my popular eBook Jumpstart Your Style.



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Comments, Feedback, & Opinions:

  1. Michele sprague says:

    I love all the advice on this site, and follow it the best I can. I like to think that I’m reasonably pulled together every day.

    I LOVE LOVE leggings and long tops with flats. It’s perfect for my lifestyle. I’m an artist and need to be comfortable and casual, but able to whip,off my smock when customers arrive or when I have to run an errand, and look presentable. But I can never find long tunics. Ones that cover my rear and have enough weight and swing to them to hang nicely.

    What stores carry such tops? I search the internet often but don’t have much luck.

  2. Diana England says:

    Glad I found this site! I’m about to turn 49 and my ‘style’ is changing. I am most comfortable in jeans and a t-shirt or sweat pants and sweatshirt – but now, I’m going thru a divorce and need a boost! I’m NOT dressing for ANY man, I’m dressing for ME! Same with my hair… My husband always wanted me to have LONG hair, but it’s not ‘flattering’ on me. It just ‘hangs’ there…I prefer something like Lisa Rinna wears. I had my hair like that for YEARS and LOVED IT, but my husband wanted me to have ‘sexy, long hair’… Yeah, we’ll if HE had to style it every day he might think different! Plus, I don’t think a ponytail looks attractive on most grown women… I WISH I were one of those women that could wear a stylish ponytail, but my face-shape isn’t made for it… So, I am going back to my short hair!! I can wash it, style it and use a little styling product for definition and it’s DONE!! Believe me, I envy the women who can wear long hair!! But, I just don’t have time for it! They make BEAUTIFUL human-hair wigs now and also clip-in hair extensions! It’s FUN to play around with wigs! I can be blonde/brunette/black/red and even PURPLE if I wanted to! Lol! That’s the FREEDOM we have! Also, with clothing, I NEVER thought I’d like BOLD colors like red, yellow, green, purple… But, I’m finding that pairing a ‘basic foundation’ (black/white/beige/grey) and adding a colorful pant or jacket really adds a classy ‘pop’ of color without looking like a circus clown! Shoes are also important! I don’t have TONS of shoes… Just the basics. Tennis shoes: 1 white pair & one black pair. Boots: knee-high black leather, with a slight heel, and a pair of grey, knee-high UGGS. Also, 2 pair of ankle boots, brown and black. Also, a good selection of dress pumps – black/bone/nude and a ‘wild-pair’ like red or blue… Maybe snake-skin?! Then there’s the accessories!! Purses, hats, coats, jewelry!! I have a Summer and Winter purse, and one ‘funky/fun’ tote or back-pack. I have some fun hats… Casual and dressy… Coats are a must-have! A good pea-coat in black will serve you well and is timeless! Also, a leather coat that isn’t too ‘trendy’ is a staple in my wardrobe. A good ‘jean jacket’ in either the ‘usual denim’ or in colors that work for you makes a ‘fun’ statement. Another must-have in my closet is a good-quality ‘boy-friend’ blazer! I tend to go for the basic black or beige… Maybe even grey! It’s a great way to add ‘class’ to a simple pair of jeans/slacks and t-shirt without looking too dressy! Then, jewelry…. Silver and gold… Organic stones like turquoise, onyx, etc… I personally like to keep my jewelry very simple. A pair of pearl earrings, a long strand of pearls, hoops earrings – one silver pair, one gold pair, silver and gold 18 inch chains so I can swap-out my collection of pendants. I find it’s less expensive to invest in a good necklace chain and then ‘swap-out’ the pendant. Also, a collection of scarves come in handy! So, that’s my idea of building a great wardrobe – I’m NOT an expert, but this is works for me! Hope it helps you too! Thanks for any input u may have!!

  3. Thanks Deb! Just in time for an up coming trip to Mexico – I’ve been wallowing in my closet and looking for a few key pieces to add. Now I know just the things: colored jeans, a bright jacket, and a tunic.