Sometimes I’ll spot a woman whose fashion-forward look is so casual that she almost blends in with the crowd. Almost.

 

Shayna’s Rag & Bone ankle boots, luxe Burberry trench coat, and Givenchy Nightingale bag are instant standouts in the sea of tourists on Michigan Avenue. I’m always excited to photograph everyday outfits grounded in solid, high-quality staple pieces, yet slip under the radar for the sartorially uninitiated.

 

And for those of you who picked up on the use of gender-specific pronouns, that was not by accident. Men who dress well – whether they prefer the treasure-hunting thrill of thrifting or the unmistakeable ease of Trunk Club luxury – stand out like sore thumbs. Especially in Chicago, although today I’m seeing more stylish men than ever walking our streets. Just sayin’…