The Stil Trust

Meet Ashley R.

Meet Ashley R.

Hi! I’m Ashley Roos, a seasoned stylist based in Chicago. With nearly two decades in the industry, my journey has been a whirlwind of creativity and collaboration. Starting out in New York City, I immersed myself in fashion for over seven years working with top designers and buyers from the best retailers in the world. My career then took me westward to San Francisco, where I delved into personal styling working with clients from all walks of life including influencers, moms on the go and tech-CEOs. Most recently, I've focused on the interior landscape, transforming living spaces into personalized sanctuaries and was able to apply my deep knowledge in the fashion industry to the world of home design. My style philosophy? Elevated yet effortlessly cool, with a touch of the unexpected, nothing should look too perfect. From personal favorites like Toteme, Staud, Loewe, and Celine to treasures found at COS, Zara, Mango, and H&M, I’m always scouting for that perfect piece that elevates any wardrobe. I believe in the power of clothing and the confidence that it can give you. I find myself deeply inspired by art, travel, athletes, interior design, and street style. For me, style is more than just clothing—it’s a form of self-expression that connects you to the world around us. Watch how loving what you wear positively impacts your mood, your day and even those around you. Let’s create something amazing together—because great style is not just about what you wear, but how you wear it and the joy it brings to your day. I can’t wait to work with you!
Ashley Roos

Discover the Heart & Vision Behind Ashley R.'s Style

Styling Expertise

Start with a great bottom (pant, jean or skirt) to ground your whole look and build an outfit around it. Pay attention to fit over following trends.

Styling Aesthetic

Make a lasting impression at weddings, galas, and important occasions with curated looks that reflect your personal style.

Favorite Styling Piece

Build a powerful professional image with tailored business attire that boosts confidence and commands respect in any workplace.

Types of Looks I Love Styling

Stay current with seasonal trends while maintaining your unique style identity through curated seasonal wardrobe updates.

My Mission

Navigate stores with confidence using our personal shopping service to find pieces that perfectly complement your existing wardrobe.

Ashley's Looks

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Achieve Your Style Goals

Take Our 1-Minute Style Quiz First To Get Started

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Ashley had a black blouse she loved but never wore.

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She took the Style Quiz and was matched with Nicole.

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Nicole created a personalized StyleMatch® just for her.

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Now, as a Classic Member, Ashley gets styled by Nicole every month.

Ashley D.

"I loved this black blouse and it fit me perfectly when I bought it, but I didn't have time to look for a complete outfit. I thought I'd find something in my closet to go with it but I never did. I needed a fun, 'date-night' look for spring. I met virtually with my stylist. Wow! I was blown away with how well she styled me!"

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Ashley Roos | The Stīl Trust