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“It's the art of managed creativity and I love it,” says Cornell University-educated Roslyn Clayton, founder of the eponymous independent boutique Roslyn (

Born in Chicago but having worked in the corporate side of New York fashion for years, Clayton felt the desire to return home and create an outlet for emerging designers in Chicago.

Clayton founded Roslyn in 2006 in the Bucktown area and has been stocking her boutique with a well-curated collection of hard-to-find labels ever since.

Learn about Clayton’s stylistic inspirations, her attire for this year’s Arlington Million and her penchant for the elegant yet functional “hatinator” in the Q&A below.


Mary Frances Dale: Tell me about your connection to Chicago and how you started your boutique.

Rosyln Clayton: Originally from Chicago, I grew up in Lincoln Park and attended high school at the Latin School of Chicago. After graduating with a degree in Textiles and Apparel Management from Cornell University, I accepted a merchandising position at the Abercrombie & Fitch headquarters in Columbus, Ohio. Following my time at A&F, I spent a few years working and honing my skills at J. Crew's corporate office in New York City.

Roslyn -clayton

Roslyn Clayton, founder and operator of Roslyn

Ultimately, I wanted to return to my hometown to be closer to my family as well as fill a void I saw in the independent boutiques at that time. As the entrepreneurial spirit runs in my family (my parents own several Thai restaurants in Chicago and my extended family has established successful companies in Thailand), I knew that opening my own boutique would be the best way to introduce Chicago to the amazing, independent artists I had encountered while living in NYC. Located in Bucktown, Roslyn opened in 2006 and features collections from both emerging and established designers. Since opening, we have garnered attention from the media and fashion-savvy as one of Chicago’s most outstanding resources for inspiration and hard-to-find labels.


Dale: What inspired you to become part of the fashion industry? 

Clayton: I've always loved fashion (what girl doesn't?) but I also enjoy working on the more analytical, business side of the industry. At Cornell, I was able to take courses in the history of apparel and textile design as well as courses in marketing, product development and communication. The fashion management program taught me how to apply economic and marketing principles to consumer and industry issues, therefore combining the art and business side of the industry. As a merchandiser at two major retail chains and as a buyer at my own boutique, I have to look at both the emotional and artistic appeal of a garment as well as the potential in sales – it’s the art of managed creativity and I love it. 

Dale: Who is your fashion icon?

Clayton: I absolutely adore Kate Middleton, and I think she has impeccable style.  Her ability to mix high and low pieces translates to ensembles that are original, aspirational and relatable. She embodies timeless fashion while still being “on trend” and is truly a style icon.

I'm also inspired by the free-spirited, French bohemian-chic style of Jane Birkin as well as the polished style and sophistication of icon Jackie Kennedy.

Jane -birkin

Style Icon Jane Birkin 

Dale: Describe your personal style in three words.

Clayton: Comfortable. Classic. Chameleon.

Dale: What do you look for when creating the perfect race-day outfit?

Clayton: It all starts with a great-fitting dress; find the right silhouette to complement your body and make sure it has been tailored to perfection. Style your look by layering a few jewels and nice pair of heels - I always recommend nude pumps to elongate the leg, and the color works with most ensembles. Finish with a subtle box clutch and statement hat or fascinator. The key is not to over accessorize, each element of your outfit should complement each other rather than compete for attention or worse, overpower you.  

5 Race-Day Ready Outfits from Roslyn

Dale: What are some looks from Roslyn that are perfect for the races?

Clayton: We are currently transitioning to fall merchandise but found some wonderful looks for a day at the races. 

Race Day Look 1 

One of our favorite looks is an emerald green, silk chiffon maxi skirt from Alice & Olivia paired with a saffron printed tank from Elizabeth & James and vintage statement necklace. The skirt has a sheer layer effect and dramatic gusset detailing which moves beautifully with the wearer. 


red white blue Bar


Race Day Look 2

The second look features a coral and lavender jeweled necklace which pops against the textured white top and skirt by New York-based designer WHIT.

The textured fabric is a great play on pattern, and the crisp white is a lovely canvas for colorful jewels and a statement hat.


Race Day Look 3

The gray and white striped “daily races dress” is from Florence, Italy-based collection, Suite. The sweet silhouette features a tulip skirt, side-seam pockets and a bow at the back of the garment for a little surprise. 

I love this dress because it's so ladylike with a subtle preppiness and plays well off colored jewels.


Race Day Look 4

WHIT's blue and white Corrinne dress has such clean lines and is a great length for a day at the races. This dress would do well with a large, floppy hat or architectural fascinator.


red white blue Bar


Race Day Look 5

The cobalt blue dress from Wren is paired with a bright poppy chandelier necklace from Lanvin's recent collaboration.


red white blue Bar


Dale: What are you wearing to this year’s Arlington Million?

Clayton: Weather permitting, I will be wearing an Alexander McQueen metallic woven dress, Jimmy Choo nude patent booties, a black and gold box clutch given to me from my husband for Christmas and a statement ring. Headpiece to be determined! 

Dale: Your boutique is known for its selection of hard-to-find labels. Which labels or designers are your favorites?

Clayton: Steven Alan is one of the first lines I picked up for my boutique and is definitely a favorite. His namesake collection of heritage-inspired men’s and women’s casual wear is grounded in American roots with a fashionable twist. The label includes incredible jackets, shift dresses, essential shirts, and grandpa cardigans that are well made and introduce an element of downtown cool.

Nicholas K's aesthetic can best be described as “urban nomad,” their collection incorporates the most amazing, unexpected details to each piece they design. Jacket collars are lined with hidden wires to shape in any form you'd like, zippers unveil a hood inside your favorite sweatshirt, secret buttons allow you to manipulate the draping of a button-down blouse, and leather trims surround the button holes of their wax-coated outerwear. Their pieces are artistically interesting and have a clear, consistent perspective each season.

Luxury Jones designer Niki Eatman is based in Los Angeles and is the mastermind behind the artfully eccentric fashion label. Niki works with vintage fabrics and deconstructs retro pieces into fun reincarnations - a sequin cocktail number morphs into a tattered rock halter, an old wedding gown emerges as a Lolita-esque trapeze dress. Every garment is a one-of-a kind, handmade creation and labor or love.

Sir designer Joanna Baum describes her pieces as “softly deconstructed classics” full of “old-school touches.” The label is inspired by vintage chic, Parisian sensibilities, and bias-cut elegance.

“I like to think that I’m willing to work with clients and give them a level of attention that might be more traditionally associated with a tailor,” says Baum, an award-winning fashion graduate of the Rhode Island School of Design.

With Kirsten Dunst, Kate Hudson, Keira Knightley, and Michelle Williams already counting themselves among Sir fans, historically, the label’s specialty is its bias-cut silk pieces offering great fits.

Dale: Do you have any favorite local Chicago designers?

Clayton: I've had the pleasure of working with Chicago-based designer Elise Bergman ( for the past six years. Using luxurious silks and pairing them with organic cottons, hand-dyed or hand-woven natural materials, and rare, vintage fabrics, she designs multifunctional pieces that are classic and elegant with a sustainable, feminine and youthful twist.

Over the years, we've expanded our selection to include Elise's handmade leather belts, clutches, and limited-edition silk and organic cotton pillows. The Elise Bergman Studio at Roslyn launched in 2009 and offers the largest assortment from her seasonal collection as well as one-of-a-kind pieces. Not only is Elise one of the most talented designers I've met, but she is the sweetest and most honest person to work with and support.  She has artistic integrity and a responsibility to the business.

 Elise -bergman

Chicago Designer, Elise Bergman’s collection can be found at Roslyn.

Mineralogy is a collection of limited edition and one-of-a-kind jewelry designed and handcrafted by Chicago local Theresa Cowan that we picked up a few years ago and is one of my favorites. Mineral specimens are the focal point of the intricate collection and each piece is made impressionistically with the experimentation of materials as the base of the design process. The majority of minerals used are uncut and unpolished to display their unique characteristics. The styles are produced in limited quantities, with each individual piece unique in its own aspects due to nature's wonderful aberrations. Theresa brings us new pieces on a bi-weekly basis since the line has been doing so well.

Theresa -cowan

Chicago local and designer of Mineralogy, Theresa Cowan, brings new pieces to Roslyn on a bi-weekly basis.

Dale: What current summer trends do you predict will be popping up at this year’s Arlington Million?

Clayton: We'll definitely see pops of color, graphic prints (floral or abstract patterns), black and white, and bold stripes at this year's Arlington Million.

Dale: Are you a fascinator or a hat kind of gal? 

Clayton: I love a great hatinator - it combines the elegance and functionality of both hat and fascinator!


Kate Middleton wearing a functional yet elegant “hatinator.”

Make sure to stop by Roslyn while in Chicago to find the perfect outfit and accessories for the Arlington Million this Saturday.


2035 N. Damen Ave.

Chicago, IL, 60647




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