With fall on the horizon and personal stylist Rachel Boedecker leading the way, we spent an afternoon exploring Chicago’s North Shore to preview what the autumn has in store. A former Trunk Club and Nordstrom pro, Boedecker brings a signature mix of efficiency and elegance to everything she does—always with a hint of play. Shopping with her felt less like a masterclass in elevated dressing.
When asked what fall staple is trending, Boedecker doesn't hesitate: “The classic straight leg jean never goes out of style, but adding a pair of novelty denim is the closet upgrade you didn’t know you needed. Think two-tone washes, fun details, or a fresh silhouette to instantly modernize your look.”
We began at ENAZ Boutique (444 Central Ave., Highland Park), a longtime go-to for women’s fashion with an easy, on-trend sensibility. Known for combining streetwear ease with wearable polish, ENAZ caters to those who want to look pulled together without overthinking it.
“Never underestimate the power of accessories,” Boedecker says mid-browse. “Sometimes the smallest details can make the biggest impact. A cool belt, a layered necklace, or a perfectly tied scarf can take your look from simple to styled in seconds.”
In Winnetka, Styles & Smiles (946 Green Bay Rd.) offered a quieter kind of luxury. Curated by owner Marina Trakhtenberg, the boutique leans into refined textures and timeless shapes—tailored jackets and rich knits. These elevated picks speak to women who want style without shouting.
We make our way to Wilmette’s Hubba Hubba (1101 Central Ave.), where owner Julie Cohen’s boutique hits that elusive sweet spot: classic, modern, approachable. With help from standout manager Jen Santo, Boedecker explores bold scarves, clean-lined separates and cozy layers.
Our final stop: Lori’s Shoes (311 Happ Rd., Northfield), where boots, bags and unexpected footwear offer the perfect punctuation.
Fall, it seems, is looking both fresh and familiar.
Look 1: ENAZ Boutique
Gracia Flower Embroidered Striped Shirt in Blue); Bishop + Young, Ford Tencel Pull-On Pant in Blue; Markang, Large Gold Bubble Initial Necklace; Designed by Denise, Wide Puff Heart Necklace on Chain; Markang, Snake Bendable Cuff; Juice Firenze, Mini Shoulder Bag; Caddis, Hooper Readers in Polished Gold and Yellow; D’Amelio Footwear, Lessia Sandal in Blue Jean.
Look 2: ENAZ Boutique
Le Jean, Studded Frankie Barrel Midrise Jeans; Esqualo, Gathered Sleeve City Blazer; ASTR, Ninette Bodysuit; Brave, Doone Belt; Juice Firenze, Suede Satchel Bag; Allison Fiutak Designs, Flat Bean Necklace; Markang, Snake Bendable Cuff; Leeada Jewelry, Thats So Goode Heart Ring; Leia, Art Deco Puff Wrap Ring.
Look 3: Styles & Smiles
Hidden LA Tie Waist Clean Stretch Wide Leg Jeans, an ultra-flattering wide leg jeans in a soft light wash; Allison NY Beaded Mariana Cardigan Beaded Mariana Cardigan features subtle sparkle with sequin and beading throughout the cotton crochet fabrication. Designed with a ribbed scoop neckline, leading to pearl buttons at the center front. The body and sleeves are fully lined.
Look 4: Hubba Hubba
Current Air Los Angeles Sleeveless V-neck Pleated Dress; Local designer VB & Co. Paris France Eiffel Tower necklace, French boutique and VB & Co. Simple Layering Matte Gold Paperclip Chain; Joy Susan Odette Mini Tote Crossbody with Blossom Cherry Purse Charm Key Chain; Hubba Hubba Collection Scarf.
Look 5: Hubba Hubba
RD Style Barni 5 Pkt Barrel Jean; RD STYLE Layers of Cozy Black & White Striped Sweater; Local designer VB & Co. French medallion coin horse jewelry boutique fall and VB & Co. Simple Layering Matte Gold Paperclip Chain; Alyssa Woven Shoulder Bag; Camel Coat.
Look 6: Lori’s Shoes
(Clockwise from top) Steve Madden Henrietta Cow Print Sandal, Color Cow Haircal; Tony Bianco Gatsby Loafer, Color Espresso Suede; Gola Elan Sneaker Color Mocha/ White; Tony Bianco, Bianca Black Nappa Leather Flat; Dolce Vita Baylee Ballet Flat, Color Pecan Perforated Suede; Ángel Alarcón Cleo Kitten Heel Bootie.
Rachel Boedecker is a seasoned personal stylist with 15-plus years of experience refining wardrobes and reigniting confidence. Formerly with Trunk Club and Nordstrom, she helps clients from the city to the North Shore discover their style DNA, curate wardrobes, streamline their closets and make getting dressed feel effortless—and fun. Instagram: @thestyleeditco