I have a confession. For years I only wore flats because I convinced myself I couldn’t walk in anything with even a little lift to it. My sister Jenna used to tease me about it endlessly.
Then one day I found a pair of gold heels with a thick, sturdy base, and everything changed. I could actually WALK in them. All day, on cobblestones, even.
If you’ve been dreaming of dressing up a little more this season without hobbling home barefoot at the end of the night, welcome. These are the looks I reach for again and again.
20 Ways to Style a Heel You Can Actually Walk In
Gold Heels With White Slip Dress
A white slip dress and a pair of gold heels is the kind of pairing that just works, no matter where you are going. Simple, a little glam, and easy to throw on when you can’t decide.
I wore this to a summer garden party last June and felt like a million bucks. The gold picks up the light in every photo, which of course is half the reason I keep going back to it.
Black Kitten Heels With Barrel Jeans
Barrel jeans have that rounded, roomy shape that looks so current right now, and a low black kitten heel keeps them from looking too casual. It’s a great denim heels outfit for when you want to look a little pulled together but still feel like yourself.
Tuck in a plain tee and add a small bag.
Red Kitten Heels With Capri Pants
Capri pants had a moment when I was in high school and honestly I never fully let them go. Paired with a red kitten heel and a striped top, this whole look has that French-on-the-Riviera feeling that I adore.
The red at the foot is the little pop of interest. Keep everything else neutral and let those shoes do the talking.
Beige Heels With Linen Waistcoat Set
A matching linen waistcoat and trouser set feels so polished, and beige heels blend right in so your legs look a mile long. This is my go-to for lunch dates when I want to look like I have my life together (I do not, but the outfit says otherwise).
Chunky Heels With Denim Maxi Skirt
A long denim maxi skirt with a chunky heel peeking out at the bottom is such an easy weekend look. In fact, I basically lived in this combo all last spring.
The chunky base means you can actually stroll through a farmers market without wobbling, and the maxi skirt keeps it feeling relaxed and cool.
Gold Heels With Chocolate Satin Dress
Chocolate brown satin is so underrated. Something about the deep warm color next to gold heels feels rich and expensive, even when the dress is not.
I bought a chocolate slip dress on a whim two autumns ago and it has become one of my most reached-for pieces. And the gold heels? They come out every single time.
Black Kitten Heels With Column Skirt
A sleek column skirt, the kind that skims straight down, looks so elegant with a delicate black kitten heel. This is the outfit I wear when I want to feel like I know what I’m doing.
Add a tucked-in blouse and simple gold earrings. Done.
Red Kitten Heels With Butter Yellow Dress
Butter yellow was EVERYWHERE this year and I fully gave in. A soft buttery dress with a red kitten heel is such a fresh, happy combination, like a little burst of sunshine walking down the street.
Red and yellow shouldn’t work together but they absolutely do here. Trust me on this one.
Beige Heels With White Palazzo Pants
Wide, flowing white palazzo pants with beige heels underneath is the definition of breezy and chic. The heels hide right under the hem so you get all the height.
I wore this on a trip to visit my friend in Charleston and it survived a full day of walking and a boat ride. High praise.
Chunky Heels With Tailored Bermuda Shorts
Tailored Bermuda shorts have gone from frumpy to fabulous, and a chunky heel is exactly what makes them look intentional. Pair them with a fitted top and you’ve got something that feels both dressy and easy.
This is a great one for those in-between days when it’s warm but you want to look a bit more put together than usual.
Gold Heels With Black Bandeau Dress
A simple black bandeau dress and gold heels is my little black dress formula, upgraded. The gold warms up all that black and keeps it from feeling too severe.
Throw a light cardigan over your shoulders if the evening turns cool. That small touch makes the look feel finished.
Black Kitten Heels With Lace Midi Dress
Lace can go one of two ways, sweet or a little too much, and the black kitten heel keeps it grounded and grown-up. A lace midi dress with these delicate heels feels romantic without trying too hard.
If you love a louboutin heels outfit but want something more everyday, this is the softer, more affordable cousin of that idea.
Red Kitten Heels With Dark-Wash Jeans
Dark-wash jeans and red kitten heels is one of those combos I fall back on again and again. The deep denim makes the red look even more striking, and the heel takes plain old jeans somewhere a little more special.
A crisp white shirt tucked in completes it. So simple, so good.
Beige Heels With Draped Maxi Dress
A draped maxi dress that pools a little at the floor with beige heels underneath is pure elegance. My sister wore this to a wedding and three people asked her where the dress was from.
The beige disappears under the hem so it’s all leg and flowing fabric. Very flattering, honestly.
Chunky Heels With Sheer Midi Skirt
The sturdy heel balances out the delicate, floaty skirt.
Layer a slip underneath and you’re set. I like this for date nights when I want to feel a little dressed up but still be able to sit comfortably through dinner.
Gold Heels With Cream Trouser Suit
A cream trouser suit with gold heels is the outfit that makes me feel most like a boss. There’s something about a matching suit in a soft cream tone that just reads confident and calm.
The gold heels add the tiniest bit of shine so the whole thing doesn’t feel too corporate. This is the classic block heels outfit I recommend to everyone who says they have nothing to wear to a work event.
Black Kitten Heels With Satin Slip Skirt
A satin slip skirt catches the light so beautifully, and a black kitten heel keeps it from sliding into too-dressy territory. Wear it with a simple knit tucked in for daytime, or a sleeker top for evening.
This is my favorite kind of piece, one thing that can go so many directions depending on the mood.
Red Kitten Heels With Polka Dot Dress
Polka dots and red kitten heels feel a little retro, a little playful, and I am here for all of it. A black-and-white polka dot dress with a red heel is such a cheerful, vintage-y look.
I imagine wearing this to a Sunday brunch and taking approximately one hundred photos. And that’s a good day in my book.
Beige Heels With Suede Mini Skirt
A suede mini skirt in a warm tan with beige heels is a cozy, autumnal kind of outfit. The textures play so well together, all soft and warm and easy.
Add a chunky knit sweater and you’ve got the perfect look for a crisp fall afternoon. This is one I reach for the second the leaves start turning.
Chunky Heels With Oversized Blazer Dress
An oversized blazer worn as a dress is a bold move, but a chunky heel makes it feel deliberate and cool rather than like you forgot your pants. The sturdy heel balances all that structure up top.
Belt it if you want a little shape, or leave it loose. Either way it’s a statement.
