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Today I’m breaking down everything you need to know about Walking around Chicago in red Mary Jane’s.
From undertone matching to my step-by-step application and styling routine across 4 detailed parts.

Pin Look
1. Why I Love Walking around Chicago in red Mary Jane’s in My Beauty & Style Studio
Last fall, I had a client who was nervous about wearing her cherry red Mary Janes for a full day of gallery hopping in the Loop.
She kept saying they were ‘too loud’ until I paired them with a simple cream knit dress and a cropped leather jacket.
Suddenly, the shoes became the star, not the shout.
That’s the magic of red Mary Janes: they add a playful, confident jolt to even the most understated outfit.
This look works because it balances the boldness of the shoe with neutral, textured layers.
The red pops against the city’s gray tones, and the Mary Jane’s strap keeps it youthful yet polished, so you feel put-together without trying too hard.
✦ Nadia’s Backstage Notes (Part 1 of 4)
- Real-Life Wearability: Tested to look just as flattering in natural daylight as it does under camera flash.
- Undertone Harmony: Always match the intensity of the finish to your natural skin and hair contrast.
- Pinterest Reference: Tap Pin Look to save this reference directly to your moodboard.
Tap Continue Reading (Page 2) below to see how I customize the undertones, finishes, and proportions for different features.