How to wear a sack this summer

An ode to dressing "unflatteringly"

One of the most brilliant realizations that came from my Great Closet Overhaul™ was that I only ever wanted to wear anything that made me comfortable. I’m not talking about “comfort” in the abstract, like being comfortable in my own skin. I’m talking literal comfort by means of elastic waists, oversized sweaters, and dresses with zero discernible shape. If a piece clung, or pinched, or squeezed, or left behind marks, I wanted it banned from my closet — full stop.

Up until that point, I was dressing to fit into some societal definition of “flattering,” which is a concept I absolutely despise in the same way I loathe the idea of “dressing for one’s body shape.” It’s a common, albeit wholly toxic, refrain that we hear as women, especially if, like me, you grew up during the early aughts when fashion magazines were at the peak of their problematic history. And as a straight-sized person, I wasn’t subjected to half of the questionable “advice” directed at women at the time.

But I’d consume styling stories that likened my body to different fruits (apple, pear) and interviews with men on the very important topic of what women should wear to be “hot” (skirts, heels, thongs). And since I was dating and desperate to do everything I could to make myself desirable, I followed those “rules” — nipping in my waist, showing off my legs, and wearing heels even though they made my feet scream. I hated those clothes, but in my mind, the goal of dressing was to appear outwardly attractive. Comfort didn’t factor into the equation.

However, being deemed a babe by the opposite sex was not the goal of the Great Closet Overhaul. The goal instead was to build a wardrobe that I loved and that I felt good in. And once I adopted that mindset, I saw myself gravitating toward pieces I hadn’t allowed myself to enjoy in the past — like the humble sack dress and caftan.

A small sampling of the sacks I’ve since begun to acquire.

Turns out, there is nothing I love more than throwing on a billowing mess of fabric and wafting down the sidewalk like a 50-something, overly-tanned hostess holding court poolside in Palm Springs. A dress without a defined waistline checks so many boxes for me. Yes, many come in incredible colors and patterns (not to mention fucking *marabou sleeves*, for the love of god) but there’s more than that. Caftans and sack dresses are the one-pot meals of getting dressed — toss one on with a fun pair of shoes and you’ve got a whole-ass outfit in seconds flat. And, honestly, they keep me cooler than a tank top and shorts in the summer because when I’m hot, the last thing I want is something clinging to me.

But, most importantly, they aligned with my big realization — they’re COMFORTABLE. There is nothing I hate more than feeling like my clothing is tight around my midsection, whether I’m at my desk or at dinner. I wear caftans when I’m feeling fabulous, but also when I have my period, and I’m bloated, and I just want to wrap myself in a blanket and sleep for days. The sack dress helps me look pulled together when I feel like absolute dog shit, and that does, in fact, make me feel better. Magical thinking!

If you want to give the humble sack dress a go, allow me to offer a few tips: I love caftans of all lengths, but if you’re afraid of being swallowed alive by fabric, go mini and shapeless or find an option with a removable sash belt. On the flip side, make sure not to go too long with your length — it can be easy to get tangled in the amount of fabric. And when choosing accessories, I like to contrast the vibe of the caftan. If you’re wearing something with bold patterns, go simple with the extras. More minimal? Pile on the costume jewelry.

Will these caftans show off your ass and legs? Probably not! But they make me feel incredibly comfortable, ridiculously stylish, and, most importantly, like me. And to me, there is nothing more attractive than a woman who is completely in love with what she is wearing. What could be more flattering than that?

Here are some sacks I’ve been considering lately:

1. Forever Dress by Catherine Ogust for Penthouse Gallery, $88: I have been on the hunt for a perfect Forever Dress by Catherine Ogust for ages — anyone with any love of vintage probably recognizes these colorful shirt dresses. I love the color blocking and the oversized sleeves.

2. By Anthropologie Short-Sleeve Swing Tunic Mini Dress, $148: The flare is just too cute.

3. Vintage Marimekko Striped Coat Dress, $139: The removable sash belt on this vintage Marimekko delight allows you to define your waist should the mood strike. I also am obsessed with the huge hip pockets.

1. Handmade Oaxacan Sundress, $60: Buy one Oaxacan-style sundress, and I swear you will have it in your closet forever. They’re truly timeless.

2. Fruit + Fauna Vintage Hawaiian Dress, $135: If this were my size, I would have already bought it. Please, someone with more narrow shoulder than mine, buy this gorgeous thing and wear it everywhere!

3. Vintage Striped Caftan, $110: The sunset-hued stripes are SO major. I would wear this with some nude strappy sandals and a straw tote.

1. Everlane The Linen V-Neck, $148: A friend of mine hand-made me the white sack dress that I currently own, and it will be in my closet forever. (Mostly for the cult-y vibes.) This is the closest approximation to it that I’ve found!

2. J. Crew Maxine Button-Back Dress, $98: I bought an older, blue version of this dress off ThredUp a couple of years ago, and I’m thinking about getting it in this gorgeous green linen, too.

3. Sézane Layla Dress, $248: A sack dress that is also wedding-guest-appropriate? Sign my ass up. I plan to wear this billowy number to a wedding in July.