1. Battaglia Footwear
With its highly curated shoe collection and showroom-like display, Battaglia comes off as more gallery than shoe store. However, its central Lincoln Park location and wiggle room for customizations (while most all styles are available in a variety of heel heights and colors, the owner also caters to more specific requests) assert it as the ultimate destination for your new favorite pair.
While this uber influential high-end boutique may be known for its couture frocks and decadent jewels, Ikram also plays host to an impeccable assortment of stilettos that go beyond the predictable. Our suggestion? Take a pair of python patchwork Manolos for a spin.
3. Lori’s Shoes
Lori’s Shoes has been the Chicago woman’s go-to shoe destination for more than 30 years, and for good reason—the Lincoln Park boutique has an unparalleled collection of stilettos diverse in both price range and style, from the classic Vince Camuto to the more experimental Jeffrey Campbell. If you need a finishing touch to your look, be sure to check out the store’s tempting assortment of jewelry and sunnies.
4. Luxury Garage Sale
Contrary to the name, nothing about this boutique in the 900 N Michigan Shops building reads garage sale (except, maybe, the deals). Head to the vintage section for a curated selection of high-quality stilettos from the likes of Manolo Blahnik and Valentino.
This Wicker Park boutique carries an impeccable (not to mention unique) assortment of heels inside a highly curated retail space. Don’t miss out on the store’s collection of shoes by covetable designer Rachel Comey—it’s one of very few in the Chicago area to carry her pieces.