I bought my first pair of two-tone flats years ago after saving for what felt like forever, and I still remember carrying the box home like it was made of glass. My sister thought I was ridiculous. She may have been right.
But those shoes have shown up in more of my photos than any other thing I own. And once you have a pair, the fun part begins: figuring out how to actually wear them without feeling like the shoes are wearing you.
So I put together 20 outfit ideas that I fall back on again and again.
20 Ways I Actually Wear My Favorite Designer Shoes
Two-Tone Flats With Straight Jeans
This is my everyday go-to, the one I could do in my sleep. A pair of straight-leg jeans, cropped just at the ankle, so the black cap toe of the flats peeks out. Add a plain white tee and you are done.
The black toe does something clever here: it visually shortens the shoe, which somehow makes your ankle look a little more delicate. That’s the whole trick. Jeans and flats, but suddenly it looks like you tried.
Chanel Ballet Flats With Capris
My mother wore capris with flats her entire life and I used to roll my eyes, and now here I am. A chanel ballet flats outfit with slim cropped capris is the most flattering thing for anyone who feels short (me, hello).
Keep the capris a solid color, cream or navy, and let the shoes be the interest. A little boat-neck top on top and you look like you’re headed somewhere lovely on the coast even if you’re just going to the post office.
Tweed Jacket With Mini Skirt
Okay, this one feels fancy but it’s honestly not. A structured tweed jacket over a matching or nearly-matching mini skirt, with the flats keeping it from tipping into costume territory.
I wore something like this to a lunch with an old friend and she asked if I’d gotten dressed up for her. I had. I will not lie to you.
Chanel Sneakers With Wide-Leg Trousers
Comfort with a little polish. A chanel sneakers outfit paired with high-waisted wide-leg trousers is my travel-day uniform because I can walk for miles and still look put together stepping off the train.
Tuck a fitted top into the trousers so the volume of the leg has something to balance against. The sneaker peeks out just at the hem. So easy.
Jennie-Inspired Tweed Mini Dress
If you’ve spent any time online you’ve seen the jennie chanel outfit photos, and honestly they’re the reason half of us wanted tweed in the first place.
I’d add sheer socks or bare legs depending on the season. And a small shoulder bag, nothing heavy. The dress is doing the talking.
Chanel Boots With Skinny Jeans
Fall arrives and out come the boots. A chanel boots outfit with dark skinny jeans tucked right in is the kind of thing that looks expensive and takes zero thought.
I like an oversized sweater on top, something slouchy, so the sleek boot and the slim jean feel intentional against all that softness. My favorite way to dress for a chilly Saturday of errands.
Ballet Flats With Pencil Skirt
This is what I wear when I want to look like I have my life together at the office. A knee-length pencil skirt, a tucked blouse, and the flats instead of heels.
People underestimate how sharp flats look with tailored pieces. You get all the polish of the skirt and none of the wobbling at the copy machine.
Chanel Flats With Bermuda Shorts
Bermuda shorts came back and I am so pleased about it. A chanel flats outfit with tailored Bermudas hits that sweet spot between summery and grown-up.
Go for shorts that end right above the knee in a crisp fabric, then a tucked shirt. The flats keep the leg long and clean. This is my errand-running look the second it warms up.
Tweed Vest With Matching Shorts
A little tweed vest and matching shorts set is one of those things that photographs beautifully and feels breezy in person too. Flats finish it perfectly.
I wore a set like this to a garden party last summer and got asked three times where it was from. I did not tell them it was two separate pieces I’d found on sale. A magician never reveals.
Chanel Sneakers With Slip Skirt
The slip skirt and sneaker combo is possibly my favorite trick in the entire post. The silky skirt looks delicate, the sneakers ground it, and together they somehow look effortless (I know, banned word energy, but you get me).
A plain fitted top tucked in the front only. Sneakers laced up. I’ve worn this to brunch, to the movies, to a very casual work thing. It never fails.
Blue Ballet Flats With Black Capris
Sometimes the shoe should be the pop of color, and a soft blue flat against black capris does exactly that. It’s such a small choice but it changes the entire outfit.
Keep everything else quiet. Black capris, a black or gray top, and let those blue flats do the work. My friend Dana calls this my “sneaky color” look and she’s not wrong.
Jennie-Inspired Cardigan And Mini Skirt
Here’s another one for the pop-star files. A cropped cardigan buttoned up, worn with a coordinating mini skirt and flats, is sweet and a little bit preppy in the best way.
Add pearl earrings if you’re feeling it. This is the outfit I’d wear if I wanted to feel about ten years younger, and In fact I did wear it, and it worked.
Chanel Boots With Tweed Shorts
Tweed shorts with tall boots is a cooler-weather combo that I adore. The boot covers the leg so the shorts read as chic rather than chilly, and the textures play off each other beautifully.
Throw on a chunky knit and you’ve got the perfect look for a crisp autumn walk. I did this on that Vermont-style leaf drive my husband still won’t stop talking about.
Two-Tone Flats With White Jeans
Crisp white jeans and two-tone flats is the freshest thing I can think of. So clean, so easy, and the black cap toe keeps the white from feeling like too much.
A striped top on top and you’re basically living in a coastal town in your imagination. Which, some days, is exactly where I need to be.
Chanel Tweed Jacket With Denim
I love mixing something fancy with something plain. A chanel tweed outfit built around a structured jacket over a simple white tee and blue jeans is the perfect example of that high-low thing I can’t stop doing.
Flats or a low boot, either works. The jacket does the heavy lifting. And the denim keeps it from looking like you’re trying too hard. So good.
Soft Ballet Flats With Summer Suit
A lightweight summer suit, the kind in linen or a soft cotton, looks unexpectedly lovely with delicate ballet flats instead of heels. It softens the whole thing.
I wore this to a daytime wedding once and my feet thanked me for hours after everyone else had kicked their shoes off under the table. Flats win. They always win.
Chanel Sneakers With Pleated Mini Skirt
A pleated mini skirt with sneakers is that sporty-but-sweet look that never seems to go away. The pleats move when you walk and the sneakers keep it grounded.
A fitted knit tucked in and maybe a little baseball cap and you’ve got a very cute weekend outfit. My daughter borrowed this one and did not give it back. That’s how you know it’s good.
Tweed Mini Dress With Knee Boots
Take that tweed mini dress and swap the flats for knee-high boots and suddenly it’s a fall outfit. The boots stretch the leg and make it look intentional and sleek.
This is the kind of thing I’d wear to a nice dinner in October. A little clutch, some gold earrings, done. The boots make it feel finished without a single extra thought.
Chanel Flats With Satin Midi Skirt
A satin midi skirt has this beautiful drape and shine, and flats keep it from feeling overly formal. It’s a look that goes from a work meeting to dinner without a single change.
Tuck in a fine knit and let the skirt catch the light. I’ve had this exact chanel shoes outfit save me on a day when I had absolutely no idea what I was doing but needed to look like I did.
Jennie-Inspired Cropped Tweed Set
And we end where the trend really started for a lot of us: a cropped tweed set, the little jacket and the matching skirt or shorts, styled with flats. It’s polished, it’s playful, and it feels like a moment.
Wear it with confidence. Add the pearls. Take the photo. This is the outfit that made me finally understand why everyone was so obsessed, and now I’m one of them too.
