I turned a certain age a while back and suddenly all the advice I found online seemed to be about hiding, covering up, or “flattering” myself into a corner – honestly, I got a little tired of it.
My mother, who is well into her seventies and sharper than me on most days, has never once dressed to disappear. She wears what she loves and walks into a room like she owns it. That is the energy I want.
So I made myself a list. A big, rambly, happy list of looks I actually reach for or admire on my sister and my friends.
20 Looks You’re Going to Love
White Shirt With Wide-Leg Trousers
There is nothing quite like a crisp white shirt tucked loosely into a pair of wide-leg trousers. It’s the outfit I put on when I don’t know what to wear but I need to look like I have my life together (even when I very much do not).
Roll the sleeves. Add a slim watch. Leave the top button open. That’s it, that’s the idea. It works for lunch, it works for an art gallery, it works for a long afternoon of doing not much at all.
Monochrome Knit Set
A matching knit top and knit bottom in one soft color is possibly the coziest way to look chic without trying. My friend Dana lives in these now. She calls them her “fancy pajamas” and she is not wrong.
Oatmeal, soft gray, a warm caramel. Pick a shade you love and let the whole thing be one calm color from top to bottom.
Linen Blazer And Straight Jeans
So here is where I admit I own more linen blazers than any one person needs. A relaxed linen blazer thrown over straight jeans is the outfit that carries me through spring and half of summer.
Cashmere Sweater With Satin Skirt
This is my favorite kind of contrast: something soft and cozy on top, something that catches the light down below. A fine cashmere sweater with a satin midi skirt looks so much more thought-out than it actually is.
I wore a version of this to my niece’s engagement dinner and three people asked where I got the skirt. In fact, the skirt was old. Very old. But the cashmere made it look new again.
Tailored Blazer With White T-Shirt
The plain white t-shirt is underrated and I will not be quiet about it. Put a tailored blazer over one and you have the single most versatile look a woman can own.
It’s the outfit that says you got dressed on purpose but you didn’t lose sleep over it. Wear it with jeans, wear it with trousers, wear it with almost anything. Good outfits for women over 60 often start with exactly this kind of simple, sturdy foundation that you can build on however you please.
Striped Shirt With White Jeans
A navy and white striped shirt with white jeans is the closest I get to feeling like I’m on holiday even when I am standing in my own kitchen. It’s fresh, it’s easy, and it photographs beautifully (my daughter takes all my photos and she approves of this one).
Add a straw bag in warmer months. Add loafers when it cools down. The stripes do all the work.
Silk Blouse And Tailored Trousers
When I want to feel polished but not stiff, I reach for a silk blouse with tailored trousers. Silk just drapes so nicely and it moves with you, which matters more as the years go on, I think.
Choose a color that lights up your face. For me that’s a soft blush or an ivory. For my sister it’s emerald green, and honestly she looks incredible in it every single time.
Matching Knit Top And Midi Skirt
A knit top with a matching knit midi skirt is another one of those quietly clever looks. Same color, same texture, top to bottom, and suddenly you look like you planned your outfit for a week.
It skims the body without clinging. It’s warm. It’s comfortable. And you can pull it together in about ninety seconds flat, which is my kind of morning.
Long Cardigan With Straight-Leg Jeans
The long cardigan is my security blanket and I am at peace with that. A longer, drapey cardigan over straight-leg jeans and a simple top is what I throw on for errands, for coffee, for basically every ordinary Tuesday.
Keep the cardigan neutral so it goes with everything. Add a leather belt if you want a little shape, or don’t bother and let it hang loose. Both work.
White Button-Down And Linen Pants
A white button-down with breezy linen pants is what summer looks like in my head. It’s cool, it’s easy, and it never once made me feel overdressed or under-dressed.
Untuck the shirt or half-tuck it (the half-tuck is my personal favorite, I will not lie to you). Slip on flat sandals and you’re ready for a garden lunch or a long walk by the water.
Sleeveless Vest With Wide-Leg Trousers
Now, a sleeveless tailored vest paired with wide-leg trousers feels a bit more fashion-forward, and I love that. My niece talked me into trying it and I was hesitant, but she was right, of course.
The vest gives you structure through the middle while the wide trousers keep everything airy and relaxed.
Relaxed Blazer With Dark Denim
Dark denim just looks expensive, I don’t make the rules. A relaxed blazer over a pair of dark jeans is my go-to when I want to look like I made an effort but I truly only spent two minutes deciding.
The blazer should be soft, not boxy. Something with a little give in the shoulders. Add a plain tee underneath and low shoes and off you go.
Neutral Trench And Monochrome Layers
A classic neutral trench thrown over layers in the same soft color family is the definition of quiet elegance to me. It’s the look I always associate with women who seem completely at ease with themselves.
Cream over cream. Camel over beige. Keep it all in one tonal range and the trench ties the whole thing together. I bought mine years ago and it still looks as good as the day I got it.
Cashmere Polo With Tailored Pants
A fine cashmere polo with tailored pants is such a smart, grown-up combination. There’s something about that little collar that makes an outfit feel finished.
My husband, who notices nothing, actually commented the first time I wore this. He said I looked “very put together,” which from him is basically a standing ovation.
Midi Shirt Dress With Ballet Flats
The midi shirt dress is a one-and-done wonder. One piece, zero decisions, and you still look like you thought about it. Add ballet flats and it becomes the easiest outfit you’ll wear all season.
Belt it at the waist or leave it loose and relaxed. Both look lovely. In fact this is the dress I pack first for any trip because it does so much and takes up so little space.
Fine Knit Sweater And Pleated Skirt
A fine knit sweater tucked into a pleated skirt is the softest, most feminine look on this list, and I mean that as the highest compliment. The pleats move so beautifully when you walk.
Keep the sweater simple and let the skirt be the star. A midi pleated skirt in a rich color is worth every penny. I wore mine to a friend’s book club and felt lovely the whole evening.
Cream Blazer With White Trousers
Cream and white together sounds like it would be too much of the same, but it’s actually gorgeous. A cream blazer with white trousers is crisp and calm and just a little bit glamorous.
The trick is playing with texture so it doesn’t go flat. A slubby blazer with smooth trousers, or the other way around. Add gold accessories and you look like you’re headed somewhere wonderful.
Denim Shirt And White Jeans
Double denim used to scare me but a denim shirt with white jeans changed my mind entirely. The white grounds the whole thing and keeps it from looking too much.
Roll the sleeves, undo a button or two at the collar, and add simple slides. It’s casual and it’s cool and it makes running Saturday errands feel a touch more stylish. That’s a small win I’ll happily take.
Soft Knit Dress With Knee Boots
When the weather turns, a soft knit dress with knee boots is my absolute favorite thing to wear. It’s warm, it’s easy, and it’s comfortable enough to wear all day into evening.
Choose a knit that drapes rather than clings. A pretty caramel or deep berry looks so rich in the cooler months. And knee boots make your legs feel a mile long, which never gets old.
Elegant Cardigan And Slip Skirt
And to close, an elegant cardigan worn over a slip skirt, sometimes buttoned all the way up like a little top. This is such a soft, romantic way to end the list, and it happens to be one of my most-worn combinations.
The cardigan does double duty as your top, so you don’t need anything underneath but the skirt. Add delicate jewelry, add your favorite low heels, and you have an outfit that feels grown-up and gentle at the same time.
