Jill Silverstein, Jill Silverstein Group, Compass

by Chicago Agent

Describe your look:

I’d describe my style as masculine meets feminine, with a little unexpected edge. I love strong silhouettes, beautiful tailoring, interesting textures and pieces that have personality. I’m drawn to rich, earthy colors; vintage designer finds; and anything that feels a little different. 

What do you consider a “fashion don’t”?

Dressing for someone else’s approval. Fashion should be fun, and I think the biggest mistake is worrying about what anyone else thinks or asking too many opinions. 

What style has come back into fashion that you think shouldn’t have?

Ultra-low jeans. Not my thing. And unless you have a model body, I find them hard to wear for most people.

What item of clothing gets you the most compliments?

Usually the pieces that are a little unexpected. I LOVE a statement coat or jacket and collect them. Those are always well received. I love how the outerwear can become the entire outfit, especially in the winter while doing showings.

What is a fashion crime you have committed in the past?

In college, I would wear Ed Hardy dresses, extreme nude lipstick with awful hair extensions. Luckily, Instagram wasn’t around then.

Who is your style icon?

My nana. We spent a lot of time in her big closet trying out fabulous items when I was young. She is the reason I fell in love with a sale and the hunt. We would go to garage sales all over the place and find hidden gems and would dominate all the sale racks in department stores. She is always dressed with fun pieces and great jewelry.

Where are your favorite clothing stores or brands?

I LOVE The RealReal. It’s exhilarating finding deals and one-of-a-kind pieces. I love luxury vintage, designer resale [and] sample sales. There’s nothing better than scoping out the consignment stores and luxury resale places when traveling to a new city. This is my sport! I love treasure hunting! I also use Google reverse search to find special items many times a day.

What fashion accessory do you feel naked without?

A great bag. I’ve loved handbags since I was a little girl. They can totally change the entire energy of the fit. Also, sunglasses. It just pulls the whole dang thing together. You can never have enough!

What decade or time period had the best fashion in your opinion?

The 1970s were sexy, glamorous and free-spirited. Wide-leg trousers, plunging necklines, Halston gowns, leather, platforms and dramatic jewelry. The appeal: confident glamour that feels effortlessly cool.

What’s the most expensive or meaningful accessory or piece of clothing you’ve ever acquired? Do you still have it?

I have a few bags that are certainly “investment” pieces and do seem to continue to rise in value, even though I will never sell them! I believe bags are art, and I’m obsessed with finding them in the right color, leather, hardware, size, etc. … I love vintage bags that are hard to get, as well. I really like to wear my things and never wait for an occasion. Today is the occasion, and there’s always something worth celebrating and looking fabulous for!

What item in your closet do you wear the most?

Wide-legged jeans. They are just so flattering and work with so much. Or my white Prada platform sneakers. They work with EVERY pair of pants. Being shorter, I need the extra height PLUS comfort.

Does your style reflect your personal brand? If so, how?

Absolutely. In real estate, you’re constantly asking people to trust your eye, your instincts and your ability to see potential that others might miss. Fashion is another extension of that creativity. I lead a team of eight women in Chicago luxury real estate, and I think there’s something powerful about showing up as yourself. 

What is your style advice for other people in the industry?

“Dress like you’re the brand, not just representing one. Be polished, be memorable. Know your business, know your worth and wear whatever the hell you want as long as it’s not workout clothes to showings.”

Outfit Details: Blazer dress: vintage Chanel; boots: Gucci; watch: Bulgari.

 

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