Everyday Casual Outfits for Women Over 50 That Look Effortlessly Chic

Most days, you’ll find me in casual outfits. My mom even asked once why I share so many casual looks, and the truth is simple: that’s how I actually dress. Of course, “casual” doesn’t mean holey shirts or stretched-out leggings (although, let’s be honest, those sneak in sometimes, too). I like to feel comfortable but still put-together.

Today, I’m sharing three casual outfits I’ve been loving lately, featuring pieces from Frank & Eileen along with some great accessories. You can use these as outfit inspiration, no matter your budget.

A Relaxed Button-Up and Wide-Leg Jeans That Feel Polished

This outfit sums up how I wish I dressed all the time, relaxed yet polished. The lightweight Relaxed Button-Up Shirt has just the right “fallish” colors to transition into cooler weather. I can already see it paired with a caramel or rust jacket once autumn arrives. These Wide-Leg Trouser Jeans give you a pulled-together look without sacrificing comfort.

Accessories make a huge difference here. The Suede Belt and Ankle Boots pull the look together, proving that small details can elevate a simple outfit into something stylish.

Why It Works:

• Lightweight button-up is easy for layering into fall
• Wide-leg jeans add polish without sacrificing comfort
• Accessories like the suede belt and boots make the outfit look finished
• Perfect balance between everyday comfort and pulled-together style

Affordable Floral Shirts

A Casual Wide-Leg Look That Still Flatters

This look is definitely more casual than the first, but it doesn’t skimp on style. The Vintage Muscle Tee surprised me; it’s far more flattering than I expected. The extended sleeve line softens the shoulder and creates curves, which works beautifully for most body types (except inverted triangles).

The real star? These NYC Wide-Leg Trousers. They’re part of the Julianne Moore collaboration, and they may be the most luxurious jeans in my closet. They’re flowy, lightweight, and soft; you won’t believe how good they feel. Let’s just keep this between us… Joe doesn’t need to know what they cost. Lol!

Why It Works:

• Muscle tee adds shape and structure for a flattering fit
• Wide-leg trousers are flowy, lightweight, and luxe
• Casual yet refined thanks to polished jewelry and mules
• Ideal for an elevated everyday look that’s still comfy

Affordable Wide-Leg Jeans

The One-and-Done Maxi Dress Outfit

This Henley Maxi Dress is my definition of “easy chic.” It’s my go-to travel outfit since it’s comfortable enough for the car, yet polished enough for meeting friends for lunch. The deep navy color is slimming, and the cut allows for movement without looking sloppy.

To give it some personality, I tied on a Mixed Animal Print Scarf (below). It adds pattern and doubles as an extra layer when air conditioning gets a little too aggressive. A long pendant necklace provides a subtle shine, while the neutral loafers keep the look grounded and versatile.

Why It Works:

• Maxi dress = one-and-done outfit with zero fuss
• A scarf adds personality and a pop of pattern
• Comfortable loafers balance style with practicality
• Slimming navy keeps the look chic and timeless

Affordable T-Shirt Dress

FAQs About Casual Outfits for Women Over 50

Q: How does Frank & Eileen sizing run?
A: Frank & Eileen is known for their relaxed, oversized tops. I usually wear a medium or large in most brands, but in F&E, I can comfortably wear a small or medium. Their pants, on the other hand, run pretty true to size. I wear an 8 in the wide-leg trousers, which is my usual size.

Q: How can I make casual outfits look more polished?
A: Focus on accessories. A belt, structured shoes, or a scarf instantly make your outfit look intentional.

Q: Can wide-leg jeans work for petite women?
A: Yes! Just make sure the hem doesn’t overwhelm your frame. A slight heel or platform can also help elongate your legs.

Q: Are maxi dresses flattering for women over 50?
A: Absolutely. They provide coverage, comfort, and a long, lean line. Look for ones with shape at the waist or add a belt/scarf to avoid looking boxy.

Q: Do I have to invest in expensive brands like Frank & Eileen?
A: Not at all. While I enjoy mixing in higher-end pieces, these outfits are meant as inspiration. You can recreate the same vibe with budget-friendly options.

Ending

At the end of the day, casual outfits don’t have to mean sloppy or boring. A little thought in accessories, flattering fits, and quality basics can make even the most relaxed look feel intentional. I love these outfits because they strike that balance between comfort and style, which, let’s be honest, is what most of us are really looking for.

Which one of these casual looks is your favorite, the button-up, the wide-leg and muscle tee, or the maxi dress? I’d love to hear how you style your everyday outfits in the comments!

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1 Thessalonians 5:16-18 (NIV)
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