I Need To Loosen Up My Conservative Jewish Style: Where Should I Start?

Recently, for an important meeting, I wore what I thought looked professional: a beige sweater set, a black straight skirt, and pearls. But I felt like a douchebag.
Publish date:
April 24, 2013

Five years ago, I went from wearing overalls and Doc Martens to wearing A-line skirts and sweater sets. I was "an artist"; I became a Chassidic Jew (I mean I was always Jewish, but I grew up secular).

This other thing also happened, which was getting a job as the content manager on a Web development team, a team in which almost all of my coworkers dress quite conservatively. In an effort to be taken seriously in my new community, as well as at my job, I had to figure out clothes.

I did what anyone with no fashion sense would do: I took out my nose ring. I wore black and white and other nondescript colors like light blue and beige; I limited my wardrobe to cardigan sweaters, button up shirts, matching shells, and very conservative skirts. It worked. For the first time in my life, I looked professional and pulled-together, and for a hot minute I felt like I had achieved some fashion success.

But then I moved to New York, and started working in SoHo of all places. SoHo is messing with my head. The office where I work is in the same building as this advertising agency that seems to be entirely staffed by perfectly-coiffed British hipsters whose clothes look effortless but perfect. I die in the elevator each morning, feeling like the biggest nerd in the building.

For a while, I felt secure in my very conservative clothes. Like, I knew that I could go anywhere and do anything and nobody would notice or judge me. Lately, though, I am starting to not feel like myself. I had an important meeting scheduled with someone in the literary industry last week (spoiler: I am writing a book), and thank G-d it got put off to the next day.

On the scheduled day, I wore what I thought looked professional: a beige sweater set, a black straight skirt, and pearls. But I felt like a douchebag. I breathed a sigh of relief when the meeting was postponed to the next day. I decided it would be better to feel authentic than to look "professional" (professional what?), and I wore a jean skirt, a western shirt, and my favorite sweater. It was a good meeting. I felt like a human.

Spring is coming and I want to loosen the reins a little bit on the clothes. I have finally figured out that my husband actually loves me, and isn't waiting to replace me with The Most Chassidish Women Ever, a fear that I harbored (irrationally) for a while due to experiences that I had while I was dating. (Even the Chassidic drug dealer f*ck-ups wanted "a refined and modest girl who takes care of her appearance". I'm disgusted just thinking about it.)

I have also figured out that there is no set custom of dress (like dark colored skirt suits) in the Chassidic community in Crown Heights. I have to wear a skirt that covers my knees, tights or socks to cover my legs and feet, and a shirt that covers my collar bones and elbows, but beyond that I can exercise my own discretion.

But here is an example of how my own discretion is kind of wonky: I wear the same shoes almost every day. Here they are, in all their glory.

I wear these clog shoes because I can walk all over the city in them, and they're inconspicuous, and they match all of my black tights, of which I have about 30 pair and wear every single day with every single skirt I own. Would it kill me to buy a pair of tan tights and brown shoes? I am too afraid of my own lack of fashion sense to wear anything but plain black shoes (and plain black boots in the winter).

Oh, wait. I do have some extremely old and unfashionable sneakers that I wear on weekends with a long jean skirt and an old long-sleeved T-shirt, which is a travesty of fashion that should never be mentioned again.

I am starting to feel like, "Well what if I were to wear an overalls dress and a ¾ sleeve ringer t-shirt?" (Even my imagined "cool" clothes aren't that attractive.) Well, what if? I don't have kids (that is a not-fun essay for another time!), so nobody can ostracize my kids because their mom looks too punk rock.

And I have my own friends who appreciate my somewhat unusual personality, and they are not going to care if I am dressing a bit "out there" or not. There are people who will lament that weirdos like me are ruining the neighborhood, but mostly nobody will even notice. The women who might give me the stink eye on the street, whatever. Who cares? My husband isn't running for local office and I'm not trying to get my kids into yeshiva. Basically, I have nothing to lose by expressing some individuality.

I know I do like simple clothes, and that the proverbial puffy shirt is not my jam. I didn't grow up around fashion and beauty, so I can't crystallize it beyond that. I feel self-conscious in heavy makeup, like red lipstick. I think I favor clothes that are natural, but not too crunchy. At 33, I am just trying to figure it out.

What can I do? Where do I start? I have a limited amount of money to spend on clothes. I can't, like, walk into Rag and Bone and have them make me over. I'll need to use what I have (button up shirts, black, tan and grey skirts, cardigan sweaters and shells) and make it interesting. Has anyone else changed her style of dress successfully, and how?

Chaya Kurtz is on Twitter: @chayakurtz