Okay so I figured I’d actually walk around New York this week to see what real people are wearing for fall. Not that runway stuff, but actual street style. Grabbed my notebook and comfy boots Tuesday morning and just started wandering.

First Stop: Soho
Hit up Prince Street around 11am when the shops opened. Immediately noticed every third person had some version of a leather jacket. Not the biker kind though – these were slouchy, oversized ones kinda like they raided their grandpa’s closet. Saw this girl pairing hers with floral midi dress and chunky white sneakers. Genius move for transitioning seasons.
The Boot Situation
By lunchtime near Washington Square Park, my feet were killing me but wow – boot diversity! Tracked:
- Pointy toe cowboy boots (so many!)
- Platform lug soles on literally every age group
- Knee-high slouchy ones with mini skirts
Tried counting how many people wore straight-leg jeans tucked into boots. Gave up after 20.
Color Story Surprise
Expected all neutrals but nope! Bright pops everywhere. This dude in East Village rocked head-to-toe burgundy cords with matching beanie. Saw three separate people wearing electric blue coats near Strand Bookstore. And marigold yellow? Big yes for scarves and bags.
Layering Tricks I’m Stealing
Best find was near Chelsea Market. Woman wearing thin turtleneck under slip dress with oversized blazer and that new jacket-slinging-over-shoulders move. Also witnessed the return of vest layering – puffer vests over sweaters, sweater vests over button-downs. Mental note: dig out my old argyle vest.

The Unexpected MVP
Crossbody bags. Everywhere. Small leather ones, nylon sporty styles, even those mini pouch things. Watched a girl at Joe’s Pizza do the whole eat-slice-while-adjusting-bag-strap dance. Functional fashion wins.
Ended up walking 8 miles according to my phone. Feet are dead but totally worth it. Main takeaway? New Yorkers are mixing fancy and casual like pros this season. That “I threw this on” look? Yeah, took serious effort. Might try the cowboy boots with sweatpants combo tomorrow…