The moment the temperature dropped below 75 degrees in late August, I received a text from my friend Elyse that said, “It feels like the High Holidays today.” This is the correct sentiment.
In my mind, there is always a slight chill in the air on the High Holidays, despite the fact that my core High Holiday memories happened in Louisiana, where there wasn’t a chill in the air until Thanksgiving (if we were lucky).
The High Holidays smell like freshly shaved pencils and apple cider and exist on the precipice of a blank page. They’re holy and vital and sacred and nostalgic — and the perfect opportunity to dip your toe into fall fashion.
Yet every year I find myself standing in my closet with 14 minutes before I need to leave, realizing I hate everything I own and that the chunky turtleneck I dreamed about all summer is too itchy and will probably get kugel on it.
Rosh Hashanah is coming so soon (it begins the night of Monday, Sept. 22, less than one week away!). In anticipation of my impending breakdown, the Kveller team and I reached out to a few Jews whose styles we admire to learn about how they think about dressing for the High Holidays.
Bess Kalb, author of “Nobody Will Tell You This But Me,” the Buffalo Fluffalo series, and The Grudge Report
Last year I wore a wool Kallmeyer gray midi skirt, black The Row Mary Jane flats from TheRealReal (I call them Mary Kate and Ashley Brand Shoes) and a cream cotton turtleneck sweater from La Ligne. On the High Holy Days I only dress for my grandmother’s approval from beyond the grave, and I think it’s important to be a little bit itchy to honor our people’s history of suffering, hence the wool skirt. This year I will panic and wear a variation on the same. Might wear a SLIGHT heel as my youngest child is now at the age where I do not need to physically carry him from place to place, which is a tragedy.
Lisa Furman, my friend (and host of the High Holiday dinner I’ll be attending)
When I was a teenager, High Holidays meant going shopping for fall clothes with my mom. I remember this one Mexx sweater set that I got — it was a cozy gray high-waisted skirt with a matching cropped short-sleeve sweater and cardigan. I wore it with thick tights and booties and it made me feel like fall had officially arrived, despite the unpredictable temperatures. I’ve been chasing that cozy fall outfit feeling ever since. So anything that includes a warm or rustic hued sweater and a cute pair of boots — ankle, knee, doesn’t matter. I just want to feel like my favorite season of the year!
Molly Madfis, founder of almost makes perfect
For Rosh Hashanah dinners, I always aim for cozy comfort since it might be chilly and I might eat too much brisket! You can’t go wrong with a roll neck sweater with a white skirt, but also a cute blouse and pants is always good with some ballet flats! Or maybe an autumnal cozy dress like this with a cardigan or a cute trench like this!?
My friend (and author of The Elyse Edit) Elyse Ash
Rosh Hashanah dinner is when I love to (almost) cosplay Jewish Mom/Wife/Matriarch with my wardrobe. Usually this means a long-ish dress in jewel tones. Some gold jewelry. A wine-colored bold lip or nails. It’s definitely giving Autumn Anthropologie Mom at a Vineyard. Gold always feels like the “right” metallic since gold feels very honey-coded to me. And yeah, deep reds and rich wine colors just feel right? Maybe a shawl or some other kind of wool texture. Maybe a plaid or stripe print?
Jessica Berger Gross, author of “Hazel Says No”
Growing up on the south shore of Long Island back in the day, dressing for the High Holidays meant (unfortunately) pantyhose and (luckily) shopping for an outfit at the Garden City department stores. (My platonic ideal then and now: 1980s Esprit.) Synagogue was a place to pray, sure, but also to see and be seen. (And to pretend to smoke cigarette butts out of the ashtray in the women’s bathroom.) Fast forward to me living in the middle of Maine. Rosh Hashanah dinner is either at my house with my husband and our teenage son, or on the ground floor of our small town synagogue. Nobody cares what I wear. Except for me. This year I’ll either break out my flowy silk burgundy and pink Ulla Johnson dress that gives me feminist Jewess in Laurel Canyon vibes. Or else I’ll be a little more crunchy Maine and wear my favorite Babaa sweater with sailor jeans and Birkenstock boots. For Shabbat dinner in our town Sukkah, I’ll wear my prized (and super warm) Irish Fisherman wool cardigan with my comfy paint splattered vintage black Lee jeans. No matter what, there will be no pantyhose. (Editor’s note: We cut some of the details from Jessica’s description but she’s an incredible thrifter and found every one of her designer pieces secondhand or on sale.)
Jason Diamond, author of the newly released “Kaplan’s Plot”
My family Rosh Hashanah dinner usually consists of a very small group of people so we don’t get too dressed up. And since my mother-in-law cooks too much food, we’re always fighting to let us wear the pants that give us room. So I started wearing a nice tracksuit to dinner with a polo shirt under it. And since it’s an important dinner, I sort of splurge. This year, I got mine from the Japanese company Needles. I think getting a *nice* tracksuit is key.
Julie Klausner, actress, writer, comedian and host of the podcast How Was Your Week
Transitional months call for layers, and I cannot lie: I love a liminal ensemble. Gang: The time has come to drown in some tunic-length chunky knits. Got an oversized blazer? I don’t even care if it’s tweedy: roll up its sleeves and you’re cookin’. Who’s afraid of Ephron-core? Not you! Add a felt hat with a brim; who cares if your cousin calls you “Indiana Jones”? What is HE wearing? Yeah, exactly. Anyway, keep going. Don’t you dare stop layering. Find a midi skirt or a maxi dress in your closet and wear it with some boots and a cardigan. Drape a scarf over your whole spiel and either tie it or don’t. Beads? Yes. Hoops? Fine! How’s your stack? Could it use a lavaliere? How about a medallion? Exactly. Now: Consider air drying your waves for extra texture and remember that patterns, even clashing ones, are your friend. Jewish maximalism is a mitzvah. And don’t worry about earth tones if you’re not an Autumn. Jewel tones (pomegranate, anyone?) will get you where you need to be — in the book of LIVING! Happy new year.
Emma Zack, founder of Vintage Shop Berriez
Personally, I want to be comfortable since I’m sitting and eating — so I would wear an upscale flowy pant (like these) coupled with a figure hugging shirt or button down with a loafer, flat, or boot!
