Fashion Over 40: Chic Celebrity Styling Ideas

Heather Anderson
by Heather Anderson

Today, I’m taking inspiration from the celebrity fashion icon, Rosie Huntington Whitley, who is always polished, put-together and she exudes confidence.


Follow along for fashion over 40 tips, including 7 celebrity styling ideas.

1. Tan and white

For our first celebrity style idea, I’m wearing this beautiful tan blazer with an all-white ensemble underneath. This includes a knit camisole and midi skirt set.


I’m a big fan of the midi skirt/dress as this cut tends to be slimming. Rosie must be a big fan too because she wears them a lot. For footwear, we are both wearing nude mules.

Celebrity styling idea

In general, I’m not going to attempt to make an identical copy of a celebrity fashion icon ensemble, but rather use it as a starting point and personalize it to my wardrobe. 


2. Black slip dress

For this next look, I wanted to show you how versatile and wearable the oversized tan blazer can be. Underneath, I’m wearing a black slip dress–a definitive wardrobe staple.


This one drapes beautifully, the fit is impeccable and it’s high quality silk. For footwear I have these black strappy sandals from Express.


The fact that these are minimal heels and not bulky gives them an expensive look, plus they elongate my legs. 


We both have ivory pouches, however, mine is a dupe Bottega bag from the Queen Bee website.

Celebrity styling idea

3. Classic black and white

In this next fashion over 40 outfit, I love how the bodysuit cuts in at the shoulders for a slim, sleek look.


Then we have a black midi skirt, which I consider to be another wardrobe staple that you’ll find yourself wearing a ton.


We both styled this with white, strappy Bottega heels. They’re minimal, chic and don’t take away from the outfit. 

Celebrity styling idea

4. Black crop top

I’ve been seeing a lot of celebrity styling lately where crop tops are paired with oversized blazers.


This top would look great with high waisted denim or faux leather joggers like I have here, for an edgier feel. I love these joggers because they’re flattering and not super baggy like most joggers are.


I don’t care if you’re over 40 or 50, you can definitely pull off this look, but here’s the kicker: you must feel confident and you must feel like yourself. If you don’t, then swap out the crop top for a black bodysuit or cami. 

Celebrity styling idea

5. Black bodysuit with midi skirt

For this fashion over 40 look, I’m borrowing pieces (or similar options) from the other outfits. I’m wearing this black, sleeveless bodysuit tucked into the white midi skirt from look 1.


The black top is so flattering and styleable, so it was definitely worth the purchase. My rule of thumb is that if you can’t style a piece 3 different ways, then don’t waste your money on it. 

Celebrity styling idea

6. Timeless fall outfit

Like Rosie, I’ve styled an oversized, black blazer over a simple, black V neck bodysuit. Then I have blue “Mom jeans” which look like a modern take on skinny jeans. 

Celebrity styling idea

My jeans are from Express and they’re more of a slim, straight leg. They were under $100 and if you don’t like denim with rips, these are a good option.


The medium-blue wash is great all year round. Express denim feels like designer, but at a fraction of the cost.

Celebrity styling idea

For footwear, I’ve mimicked Rosie’s snake skin boots. They’re cool, edgy and perfect for fall/winter. 

Celebrity styling idea

7. All-black shorts look

The last celebrity-inspired look for today is my favorite and it inspired me to make this tutorial. Again, she’s styled a black blazer (because, who doesn’t love a good blazer?) We’re both wearing black, V-neck bodysuits. 

Celebrity styling idea

My shorts are a bit different from hers. I swear by these high waisted shorts–they’re so flattering and the inseam is a bit longer than your regular denim shorts inseam. I added sexy, gold kitten heels and a belt to make the look my own. 

Celebrity styling idea

Fashion over 40: celebrity styling ideas

Those were the 7 fashion over 40 looks inspired by Rosie Huntington Whitley. Let me know in the comments which celebrity fashion icon you’re dying to emulate with your wardrobe.


For more fashion over 40 content, check out how to look polished and fashionable on a budget

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