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Chic and Modest: 10 Tips for Dressing From the Soul

By Chaya Dubinsky From

Art by Sefira Lightstone

Some of the most stylish women I know are also the most modest and dignified—a blend that is an art to achieve. So I spoke with those in the know, friends, designers, and experts to get their advice for dressing chic, modest, and fabulous.

Here are some of the top pointers:

1. Be Authentic

I knew I had to call Joyce Azria, a celebrity fashion designer who had turned to Shabbat, kosher food, modest dress, and much more, in mid-career. She told me her life journey.

For Joyce, dressing modestly was a natural expression of her confidence, authenticity, and connection to G‑d. “In the life that I’ve led, I’ve been moved by people who are authentic,” she tells us, “where their inside and their outside matches.”

Joyce told how her father, Max Azria of BCBG fame, always says that fashion is a way for people to feel their confidence. So they always had an assortment that was more dignified—for those who had the confidence.

2. Get Inspiration

Modest dressing is an art. With any art, beautiful ideas are inspired by other creatives around us. Basya Stevenson, graduate of The Fashion Institute of Technology, told me about the point when she started to adopt her own modest style:

“There were so many modest fashion bloggers that I followed and I saw that they dressed super stylish. I loved their outfits and that they were expressing their Jewish identity and they were set apart from everyone else … they had their thing that distinguished them.”

My takeaway: Modest dress allows my inner self to shine through. It’s how my values enable my voice and style to speak through my wardrobe choices.

Find those styles that echo your inner voice. Inspiration is everywhere.

3.Take Baby Steps

Another thing Basya told me: “I went slowly, not going from zero to one hundred but just taking smaller steps. My shlucha told me to do it only if it came from a place of love.”

That really means two things. One is that when you’re starting off, it doesn’t have to be everything at once. You can move slowly, gradually moving from slacks to skirts, for example.

And the other thing is that you don’t have to throw out your entire wardrobe and start all over. You might already have everything you need to do the switch.

For example: Can a cardigan or blazer go over that sleeveless shirt or dress? Can a turtleneck or ribbed tee fill in that low neckline?

A sleeveless dress can be elevated with a blazer or cardigan, and a fitted white turtleneck can beautifully fill in a low neckline, but you want to make sure you’re bringing your outfit up a notch. So take a step back from the mirror and ask if it feels natural, like all those pieces are intentional.

4. Let Less Be More 

When you do start to buy, think of it as building a capsule wardrobe. Focus on a small number of easily interchangeable pieces, that will give you multiple outfit options. You can then dress these up or down with scarves, jewelry, and layers.

Shifra Sharfstein, shlucha to Georgia Tech, gave good advice: “Better a few high-end classics,” she said, “than many wear-once dresses.”

To me that means investing in timeless, versatile pieces that can be worn over and over in different ways. Keep a classic black dress you can wear for any occasion. Add a gold belt and heels, or a chunky necklace and booties. For these timeless pieces, you want to invest in good quality, natural fabrics like cotton, silk, and wool.

Gift yourself pieces that you love, that you’ll never get bored of, that you’ll come back to again and again.

5. Find the Right Places to Shop

Another thing Joyce told me: “Royalty, wealthy, and people who are dignified, dress in a more modest manner.” That’s why for designer brands and high-end stores, the clothing often trends toward the more sophisticated, i.e., more fabric, less exposure.

So, how do you get that sophisticated look while keeping your budget modest as well?

If you live in New York, New Jersey, Los Angeles, or another very Jewish area, there may be plenty of modest clothing stores not too far from you. Things are getting competitive in the modesty market, so you can often find the same styles that will sell in a high-end store selling in these stores for much less.

If not, shopping at online boutiques may be the most practical way to find modest clothing today. Some offer very decent pricing. Many give full-body measurements for each piece of clothing so you know how it will fit before it even reaches your doorstep.

Plus, what could be better than supporting a small, women-owned Jewish business? Just make sure to check the return policies, some are more flexible than others.

Then there are the high-end thrift shops—those places where those who won’t wear an outfit more than twice bring their designer clothes so you can wear the same outfit for much less and much longer.

How do you find these stores? Ask your shlucha, friend, or neighbor, where they like to shop. Don’t be afraid to ask your stylish coworker where she got that stunning dress—it’s the biggest compliment. If you’re on social media, follow some modest Jewish influencers—they’re almost always happy to share where they got their outfit.

Of course, there’s no one-size-fits-all. Every store has its definition of modest. Some pieces require layering. Knee-length dresses that actually cover the knees are easier to find if you’re on the shorter side.

But eventually, you’ll find a few stores that work well for you and keep coming back for more.

6. Filter Your Searches 

If you’re shopping at a mainstream online store, put those search filters to good use. Try searching for: midi length dress, long sleeves, round neck, plus your size and color choice. Other keywords you could try are: high neck, ¾ length sleeves, knee length, and maxi.

Another tip: Often, on the bottom of a product page, you’ll find links to similar styles you may like. Those can be super helpful leads.

7. Flatter Yourself

I also asked Joyce for modest styling tips. Her best tip: “All the things that I cared about when I wasn’t modest in terms of rules of styling would be the same rules that I use now.”

Here’s how to do that: Figure out which colors work best with your skin tone, eye color, and hair. Wear clothes that suit your body type, that flow nicely and create a beautiful silhouette. Taking your clothes to the tailor for a new hem or a cinch at the waist gives a really polished, made-for-me look.

8. Find Your Voice.

“The truth is that fashion is not about rules,” Joyce Azria reminded me. “Fashion is about finding a style that expresses who you are in an authentic way.”

To me, that means wearing clothes that make me feel beautiful, confident, royal, and most of all, that feel like me.

Basya agrees. “There are so many brands out there that are beautiful, stylish, and comfortable,” she says. “There’s tons out there so that you could find things that really feel like you.”

9. Keep Things in Perspective

Feeling overwhelmed? There are those days when it can feel time-consuming, even frustrating, and expensive.

So remind yourself: Modesty is an investment and G‑d is your partner, supporting you every step of the way. So, really, you’re saving. Because, undoubtedly, you’ll make back far more than you put into it.

10. So Let It Overflow!

For Jewish women, dressing modestly has guidelines—mainly: covering past the collarbone, elbows, and knees (different communities may have different practices and it’s best to talk with your rebbetzin to get the particulars down pat).

But modest clothing is only one detail of a bigger picture: a lifestyle of dignity, crafted of personal boundaries, privacy, and the art of subtlety. While our clothing may be the fabric of modesty, there’s a wealth more in how we share, speak, and act and what we choose to lend to the world. At the core of it all, it’s awareness of being in the presence of the King of all Kings, at all times, in all places. A mindset of respect and elevated values. And it’s a journey.

by Chaya Dubinsky

Chaya Dubinsky is a freelance writer and educator living in Pomona, N.Y.

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