Okay, so sharing how I figured out this NYC wardrobe thing ’cause man, my first trip was a disaster. Packed like a dummy thinking it’d be similar to back home – big mistake. Ended up freezing my tail off in March rain then sweating buckets by July. Decided to actually test this properly over a whole year visiting my sis in Queens.

The Winter Battle (December – February)
Started with winter ’cause it kicked my butt last time. Bought a cheap puffer jacket online – total garbage. Wind near Bryant Park sliced right through it like paper. So I shelled out for a knee-length real down coat with hood. Game changer! Wore thermals under jeans (looks dumb but who cares when it’s 20°F), layered a wool sweater, and made sure my boots had tread. Slipped on black ice near Rockefeller Center but didn’t wipe out – grip matters.
Spring Rollercoaster (March – May)
Spring’s a sneaky one. One day sunny in Central Park, next day pouring in SoHo. Learned to always carry a packable trench. Wore light sweaters over tees that I could peel off when subway platforms turned into saunas. Did the tourist thing in April with just sneakers – ruined when sudden downpour flooded sidewalks. Now I waterproof my sneakers before trips. Also, scarves aren’t just fashion – stuffed one in my daybag for when winds picked up by the Hudson.
- Core system: Tank top + long sleeve tee + zip hoodie
- Must-pack: Foldable rain jacket that fits in a fist-sized pouch
- Footwear rule: Waterproof sneakers or ankle boots
Summer Swelter (June – August)
Okay, NYC summer hits different. Humidity makes you feel sticky stepping outside. Ditched polyester blends – wore all cotton or linen everything. Those cheap tourist tank tops? Yeah, they get gross by noon. Invested in moisture-wicking tees instead. Biggest hack: kept a spare shirt rolled in my backpack. Changed once after sweating through the whole Staten Island Ferry ride. And never underestimate the subway AC – lightweight hoodie stayed on me for indoor spots.
Fall Layers Game (September – November)
Fall’s the easiest if you layer smart. Walked the High Line in October with three combos:
- Flannel shirt over tee for crisp mornings
- Sleeves rolled up by noon when sun came out
- Added light puffer vest when sun dipped
Denim jacket + vest combo saved me multiple times. Saw tourists shivering in shorts near Times Square in November – no clue why anyone would risk that. Wore my waterproof boots again ’cause fall rains sneak up.

Real talk after four trips: No perfect outfit exists. I stuff a mini backpack with “maybe” layers every morning. But testing gear through actual seasons beats any influencer packing list. Now I laugh remembering that first trip wearing flip-flops in a surprise April hailstorm. Live and learn!