How to Wear Flats with Everything

Don’t you just love taking a casual stroll with the kiddos? I know I do, especially when we match. White is so fresh and so pristine – we wear it whenever we can. And my kids never mess up their priceless white outfits, because, couture. They know better. (Picture courtesy of Dirt + Diamonds).

“This is what I thought motherhood would look like,” I told my mom. (Well, minus the awkward baby holding, but otherwise, exactly like this).

My mother glanced at the picture and literally spit out her tea. I think sometimes she wonders where I came from.

These days, I would settle for a tiny part of this picture. The ponytail, perhaps. Or the blue pumps. I’ll take the blue pumps, because my vision of motherhood always involves heels. Recently, however, I had a revelation. It’s been a long time coming.

It started, a few years ago, when Lola was a toddler and I ruined a pair of Jimmy Choos at the park. Turns out stilettos and grass don’t mix. Shocking.

And there was that other time, when I nearly twisted my ankle leaving Little Gym with Lola and a newborn Eva, sending my diaper bag and all its contents flying across the parking lot. Good times.

Ooh, and the time it seemed like everyone in our small local mall was staring as I hobbled as quickly as I could after a runaway Eva, stilettos clicking on the tile floor.

So here’s my revelation. Ready? Heels can be hard. Yes, they are gorgeous and glamorous and I will never give them up, not ever, even if I am 95 years old and hobbling, but some days just call for flats. And fortunately, right now, flats are hot. So hot, in fact, that you can pretend you are wearing them because you are so stylish and a trendsetter, and not because, you know, you can walk in them. Flats (and even sneakers) are so seriously trendy right now that street style stars have been wearing them everywhere, even to the shows at New York Fashion Week. That’s how cool they are. Cool and comfortable. Which is exactly how you will look when you wear them. Oh, and you no longer need to save flats for casual occasions. Here, 3  frump-free tips for wearing flats when you dress up:

How to Wear Flats in 3 Easy Steps

1. Make Them Intentional

The key to pulling off flats with a cocktail dress or a sleek suit is to make the flats a deliberate style choice, and not an afterthought. Your everyday black ballets won’t cut it here. A special occasion calls for special shoes, regardless of the height.

2. Make Them Memorable

A gorgeous color, shape or texture can elevate a casual style, like a ballet, and make it extraordinary. Set your look apart with pretty details, like bold hues, shine, and ankle straps.

3. Make Them Surprising

Wearing flats with a dressy dress is unexpected enough, but when those flats are menswear-inspired loafers or chunky flat boots, they become a real style statement. A contrast of styles is always fresh.

And now, three outfits that you currently wear with heels, and how a flat can reinvent them.

1. Cocktail Dress + Flats

BCBG dress, $198, on my Amazon store. Zara glitter flats, $20, Zara.com or buy similar ones here from Amazon. Ashley Williams “Plaza” flat, $170, BrownsFashion.com or find similar here. Charles & Keith mesh ankle strap flats, or find similar ones here.

I don’t have much use for actual math. Fashion math, on the other hand, I love, as in these equations.

Midi dress + short to average height body + flats = frumpdom.

Shorter dress + short to average height body + flats = fabulousness.

Yes, I know you’ve seen midi skirts with flats everywhere, and they look gorgeous – if you’re 5’10”. If you’re petite and you want to wear flats, choose a dress that hits at mid-knee, at the longest. Pick a shoe that is special, in some way, and dressy enough to hold up to a great dress. That means the black ballets you run errands in won’t work. For a modern, intentional look, look for a sleek dressy pointy toe flat or a sandal or even a heavier menswear inspired loafer.

If you remember only one thing, remember this: A flat has to be modern and of-the-moment to work with a cocktail dress. Otherwise, frumpiness looms.

2. Suit + Flats

Tahari by ASL crepe pant suit, $129, Dillard’s. Chiara Ferragni glitter flats, $275, Adasa.com or find a similar style here. Black patent loafers, Zara, $60 or similar ones here. Blue bow flats, $550, Ferragamo and very similar ones here.

Want to wear flats to work? Then you need to own them. Start with the suit. It needs to be sleek and slim and tailored. A slim skirt or ankle length pants with a slim leg will be the most flattering. (Unfortunately, you can’t wear flats with the same pantsuit that you wear with heels).

Now for the shoes. Again, they should be sleek and contemporary and very right now. You do not want a shoe that is classic, or basic, and stay far away from anything resembling a “comfort shoe”, unless your office is uber-trendy and you can pull off a pantsuit with stylish sneakers. But that’s, like, one person. On the planet. And she’s very tall. Trust me on this.

3. Day Dress + Flats

Topshop dress, $105, Nordstrom. Charlotte Russe t-straps, $23, or similar ones here. Proenza Schouler coiled strap sandal, $526, Farfetch.com or similar one here. TIBI “Kern” loafer, $425, or similar one here.

A daytime dress lends itself to flats more easily, but it’s not a foolproof combo. Ballet flats with a very round toe, when worn with a dress (except a very short dress) can make your legs look shorter, so try a shoe with a more elongated toe. If pointy toes aren’t your thing, try an almond toe, an open sandal, or, conversely, something a little clunky and weighty to add edge. A loafer or boot can work beautifully.

So whether you’re wearing flats out of necessity or choice, I hope I’ve shown you how to do it in a completely frump/stump free way. Keep the clothes and the shoes cool and current, and you can pull off flats for any occasion.