Let’s talk about getting dressed in your 40s. Because honestly? I feel like this decade has brought more confidence and ease into how I dress. I’ve figured out what I like, I know what works for my frame (hi, I’m 5’2”), and I’m no longer dressing for trends—I’m dressing for me. That’s not to say I don’t love a polished look. I just want it to feel effortless, flattering, and grown-up without being too serious.
Enter: casual chic. It’s my go-to vibe these days. Think elevated basics, well-cut denim, layers with structure, and pieces that move with you. If you’re in the same boat—or even if you’re just looking for outfit ideas that feel both comfortable and put together—here are seven casual chic looks I’ve been wearing on repeat lately.
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Plaid Blazer + Straight-leg Jeans
Blazer S | Top S | Jeans 26 | Bag | Shoes
There’s something about a plaid blazer that instantly sharpens up a casual outfit. I styled an oversized version over a clean white top and classic straight-leg jeans. Finished it with slingback heels and a small structured bag to balance the relaxed fit up top.
Since I’m petite, I like to drape the blazer over my shoulders for some nice definition overall. Also, a structured bag gives a polished touch that keeps things from reading too casual. It’s one of those looks that feels equally right for a coffee meet-up or casual work setting.
Long Sweater + Short Skirt
Sweater S | Skirt S | Bag | Boots
When the temps drop just enough for tights and boots, I love reaching for a longer sweater. I wore a gray tunic-length sweater over a black mini skirt, added sheer black tights and knee-high leather boots, and topped it off with my Gucci Marmont bag for a little glam.
This combo is great because it mixes cozy and chic so well. The skirt gives the look some shape and structure, while the sweater keeps it relaxed. And the tights + boots? Always a leg-lengthening move when you’re petite.
Tweed Jacket + Wide-leg Jeans
Jacket S | Jeans 26 | Bag | Shoes
I have a soft spot for anything tweed—it’s timeless and feels just dressy enough without being fussy. I wore a pastel blue tweed jacket over a fitted black tank and paired it with light-washed wide-leg jeans. I added pointed-toe heels and a structured handbag to finish the look.
The jacket brings a feminine flair, while the wide-leg jeans keep it modern. To keep from getting lost in the fabric (which can happen when you’re on the shorter side), I always tuck in the top and go for a heel to add some visual height.
Round-neck Jacket + Black Skirt
Jacket S | Skirt S | Bag | Boots
This one feels like an updated take on old-school elegance. I wore a white round-neck buttoned jacket over a black skirt and styled it with tall boots and a little kiss-lock clutch bag. The black-and-white combo is simple, but never boring.
I love how the structured jacket gives a little edge to the softer flow of the skirt, and the tall boots help balance everything out. I keep the hem of the skirt right above the knee to elongate the legs—anything longer and I start to look shorter than I am.
Trench Coat + Light-washed Jeans
Coat S | Top S | Jeans 26 | Bag | Shoes
You really can’t go wrong with a trench coat. It instantly adds polish to the most basic outfit. I layered mine over a lightweight gray knit and light-washed jeans, then added neutral block heels and a quilted leather bag.
What I love about this outfit is how easy it is. Perfect for transitional seasons, for running errands or grabbing lunch. I always make sure to choose a trench that hits above the knee—otherwise it starts to overwhelm my petite frame.
Black Jacket + Belted Jeans
Jacket S | Top S | Jeans 26 | Bag | Shoes
This outfit just makes me feel pulled together without even trying. I wore a black jacket over a black turtleneck and added light-washed jeans to break up the darkness. A slim belt added definition, and minimalist low heels finished it off.
It’s clean, modern, and works for almost anything. The turtleneck is fitted, which keeps the look from feeling bulky, and I made sure the jeans were a slim-straight cut that doesn’t cut me off at the ankles.
Tank Top + Wide-leg Jeans
Top S | Jeans 26 | Bag | Shoes
Some days, I just want a no-fuss outfit that still looks stylish. I pulled on a basic black tank top, paired it with wide-leg jeans, and cinched it all together with a classic black leather belt. Skin-tone pointy heels make a big difference—they give you that extra height visually without drawing too much attention.
Even though it’s such a simple outfit, it feels purposeful. That’s the magic of casual chic—it’s not about piling on trends, it’s about the subtle details: good fit, clean lines, and thoughtful accessories.
If there’s one thing I’ve learned about dressing over 40, it’s this: the goal isn’t to look younger—it’s to feel like yourself. I don’t follow rules about what you “should” or “shouldn’t” wear after a certain age. What matters most to me is whether an outfit makes me feel confident, comfortable, and ready for whatever the day brings.
These casual chic outfits are proof that you don’t need a massive wardrobe or a stylist to look pulled together. Just a few good pieces, a little balance, and some confidence go a long way.
