The list covers wide-leg trousers, plaid shirts, a dark denim jacket with a bandana, and a long wool coat over a turtleneck, and the weather decides which one you wear.
Choose the outfit whose top layer comes off and still leaves you looking finished, which the plaid shirt, the denim jacket and the wool coat all manage.
1. Wide-leg Trousers
Volume on the bottom half wants a plain, fitted top, so keep the shirt close through the shoulders and chest.
Dark shoes ground the pale grey. I like a baseball cap here because it keeps the outfit casual, though a dressier shoe will push it toward office wear.
Hem length matters most: let the trousers break over the shoe without pooling on the pavement.
2. Plaid Shirts
A brown plaid shirt worn open over a white t-shirt is the easiest fall layer I know. The tee gives the plaid a clean edge, and you can add or drop the shirt as the day warms up.
Oversized black pants work with a plaid shirt as long as the shirt hangs straight rather than billowing, which keeps the proportions balanced. Pinstripes on the trousers add pattern, so keep the plaid in muted browns to avoid a clash.
Glasses and a simple crewneck in white or gray finish it without effort.
An oversized plaid button-up is a key layering piece for fall. Trendsetters in Manhattan neighborhoods like the West Village and the Lower East Side have been mixing them with other checked prints.
— Elle
3. Dark Denim Jacket and Bandana
Dark, cropped denim sits well over a white shirt, and a red bandana at the neck is the one loud note.
Keep the bandana the only bright piece; olive green trousers and black boots stay quiet enough to let it work.
A cropped jacket shortens the torso, so high-rise trousers suit it best. I’d choose a dark wash over a faded one because it reads sharper with boots.
A beret is optional, and I’d add it only if you’re comfortable standing out.
4. Long Wool Coat Over Turtleneck
Long wool overcoats over turtlenecks give you a column of color from collar to hem. Choose autumn shades like camel, brown, or rust, and keep the turtleneck fitted so the coat’s lines stay clean.
Wide trousers balance the length of the coat, and the hem should fall below the knee. Leather gloves add warmth and finish the look.
Wool and a turtleneck is a heavier outfit, so I’d save it for the cooler weeks of fall.
Fall Weather Considerations
A New York fall can run from the high 70s down to the low 40s, and in some years a few days climb into the 80s, so plan on layers that work across that whole range.
Check the forecast before you leave the house, because a cool morning and a warm afternoon can share one date.
Build the outfit in layers that still look finished when one comes off. A leather jacket, a barn jacket, or a cardigan that works with several outfits does the most for comfort.
Wear shoes you can walk in all day. If the weather surprises you, the city has plenty of stores to fix it.
Packing Tips for NYC
Pack fewer shoes than you think you need.
Outerwear is where suitcases get heavy. Pick one layering piece you trust and build the rest of the bag around it instead of bringing several jackets.
Choose tops and bottoms that mix with each other, so a small bag still gives you many outfits. Comfort on your feet matters more than one extra pair for variety.
Color Trends for Fall
Burgundy, olive green, and neutrals are the colors I’d build a fall wardrobe around. They mix easily, so a few pieces can make many outfits.
Keep the neutrals as the base: trousers, coats, and knits. Then add burgundy or olive in one piece at a time, such as a sweater or a bag, so the outfit has a single point of color.
Olive suede is a current favorite on New York streets this season, and a bag or a pair of shoes is a low-risk way to try it.
Frequently Asked Questions
What are New Yorkers wearing this fall?
Layers over a plain base, in autumn shades like camel, brown, rust, burgundy, and olive. Plaid shirts over white tees, long wool coats, wide-leg trousers, and cropped dark denim all show up.
Olive suede is turning up all over the city this season, and a pair of shoes or a bag is the cheapest way to test it before you commit to a jacket.
What makes a man look wealthy in fall outfits?
Clean lines and restraint. Keep the fit close on the base layer, such as a fitted turtleneck under a long wool coat, and let one piece carry the color.
A hem that breaks over the shoe without pooling and a dark wash denim that reads sharp with boots also help an outfit look expensive.
