I’ve always been drawn to clean lines and simple silhouettes. Not because they’re boring but because they give you room to breathe, to move, and most importantly, to style. They’re a great blank canvas that doesn’t shout, but it doesn’t disappear either. It’s quietly confident, which, frankly, feels like the fashion sweet spot for me after 60. Today, I’m sharing several ways to style a simple cotton dress for any and all occasions.
Hi and welcome! I’m Jennifer…wife, grandmother, and the voice behind A Well Styled Life. I started this blog back in 2012 after retiring from my work as an image consultant and personal stylist. My husband and I have been married 47 years, and while he’s patient, even he gets tired of hearing me talk about style…so I brought it here instead.
I’m 5’4″, and my weight hovers somewhere between 137 and 141, depending entirely on how strong my willpower is around potato chips (hint: it’s not). I don’t believe in dressing for the size you used to be or the one you’re aiming for…I believe in dressing the body you have today…in a way that feels like you.
If that sounds like your kind of approach, I hope you’ll stick around and join this wonderful community of smart, thoughtful women doing the same.
Today, I’m teaming up with two of my favorite blog pals, Tania and Kay, to share some summer styling ideas. If you don’t already follow them, you’re in for a treat!
Why a T-Shirt Dress Works at Any Age
Some might say a t-shirt dress is too casual or too plain once you’re past a certain age, but I disagree. In fact, the older I get, the more I value pieces that don’t try too hard. What matters is how you wear it. The shape, the fit, the styling choices you layer on top. Those are the differences between feeling invisible and feeling pulled together.
A simple cotton dress gives you options and is a great foundation for creating multiple outfits without overthinking your wardrobe. With the right accessories, layers, and even shoes, you can take one dress from errands to brunch, from book club to a baby shower…and look appropriately dressed for each.
So, if you’ve been wondering how to wear a t-shirt dress over 60, or you’re looking for outfit ideas that feel current but true to your style, here are 8 easy, wearable looks using one neutral dress.
8 Ways To Wear A Plain Cotton Dress
I’m wearing a white maxi tank dress from Aritzia here, but these looks would work with any basic cotton dress in a neutral shade like beige, gray, navy, olive, you name it. I’ve included styling notes and outfit formulas so you can recreate them with what you already own. (And yes, I wear this cotton slip and vanishing edge panties underneath, so there are no visible lines or cling. Just smooth and comfortable.😊
1. Easy Poolside Outfit Over 60: Sunhat and Sandals
This is one of my favorite warm-weather shortcuts. I paired the dress with a wide sunhat for coverage, waterproof slides that are easy to rinse off, and a lightweight tote. It’s comfortable, low-effort, and still feels pulled together…which is exactly what I want when it’s hot and I’m heading to the pool, beach, or even just the backyard.
2. Layered Look: Cardigan and Mules for Casual Comfort
Cool mornings call for a little layering. I threw on an oversized cardigan and slipped into backless mules for a mix of cozy and polished. It’s the kind of outfit I’d wear to book club or out for coffee…comfortable but still thoughtful. The soft knit adds texture without overwhelming the simplicity of the dress.
7. Chic and Structured: Belted Blazer and Brooch
Here’s an easy way to take a simple cotton dress from casual to dinner-ready. I layered on a black blazer for structure and added a wide leather obi belt to give it some shape. A modern brooch and classic pearl studs pulled it all together without making it feel too formal. It’s proof that with just a few elevated pieces, even the most basic dress can feel polished and intentional.
8. Warm Neutrals and a Statement Necklace For Luncheon
I love how soft brown and caramel tones warm up a white dress. I added a soft blazer, a braided belt (sized up so I could wrap and tuck it), and a vintage statement necklace to anchor it all. The textures do the heavy lifting here, turning something simple into an outfit with personality without adding any extra fuss.
A Few Other Simple T-Shirt Dresses
Why This Matters
When you find a piece that can shift effortlessly between errands, events, and evenings out, it earns its spot in your wardrobe. A simple cotton dress, especially in a neutral like white, navy, beige, or olive gives you the flexibility to dress with ease and intention.
It’s not about reinvention. It’s about resourcefulness.
After 60, many of us are refining our closets, not expanding them. We want fewer decisions, less fuss, and more clarity about what actually works. Styling one piece multiple ways isn’t a compromise, it’s confidence. It says, “I know what I like, and I know how to make it mine.”
Applying This to Your Wardrobe
- Start with one neutral dress that fits well and feels good. Cotton jersey or a knit blend works beautifully.
- Look at your layers. A denim jacket, linen shirt, soft cardigan, or unstructured blazer can each create a completely different outfit with the same base.
- Invest in accessories that elevate your look. A silk scarf, statement necklace, or structured tote can change the tone in seconds.
- Plan three go-to formulas using pieces you already own. Try one casual, one elevated, and one somewhere in between.
- Don’t overthink it. Your everyday wardrobe doesn’t have to be flashy to feel fresh. A strong foundation gives you freedom, and that’s the most stylish thing of all.
Do you have a simple dress that acts as a chameleon in your wardrobe? I’d love to hear how you style yours.
Now let’s go see my friends’ summer outfit ideas, Kay at Dressed For My Day, and Tania at 50 Is Not Old.
Thanks for reading, and be sure to wear what makes you feel confident!