Recently, I conducted an informal survey of two or three of my closest friends who live elsewhere and they all agreed that it's always summer in Tel Aviv. The image is of four fabulous seasons of sunshine, sunny skies and bikinis, and air conditioning cranked up to the max even in December. This was always my perception as well.
I mean, there's palm trees, and palm trees can't handle cold, so logically it never gets cold, ammiright?

This window display in Tel Aviv doesn't lie.
But the reality is that Tel Aviv wasn't built for cold and rain, and when the temperature drops below 65 the city just can't handle it. The rains when they come make the city feel damp, and colder than it would in places that understand what winter is all about, because the infrastructure isn't there and the residents don't have the right gear to handle it--like proper rainboots and coats.
And yet, most of December and January it has been downpouring almost every day.
My first winter in New York, compared to my first winter here, was far less cold. I remember snow and ice and having to watch for snow puddles. But I don't recall being cold. I had my warm coat and waterproof snow boots, and New York had the most powerful radiators this side of Siberia. The result was that when outside I was toasty in my professional cold weather gear, and when inside I was toasty in my undies laying out by the heater.
Tel Aviv Winter scenes
That's not the case in Tel Aviv. When it rains for more than two minutes, and this is no exaggeration, traffic comes to a standstill. It's as if the drivers can't believe the existence of water falling from the sky or understand how to maneuver around it. And who can blame them? Torrential rains aren't something they deal with on the regular. But when they do come water on the road accumulates into unprepared grates and floods everything, so that you better forget about keeping your feet dry if, like me, you left your rain boots back in the States with the misguided expectation that you wouldn't need them. This proves to be a special challenge when you're crossing the street, akin to Olympic Jumping, as you endeavor in vain to jump long enough to hit the one dry spot in all the street. Add to that the fact that in Tel Aviv you generally have to walk at least ten minutes to get anywhere, and now you know why I carry an extra pair of socks.
But the hardest thing about winter in Tel Aviv is brought to you courtesy of construction and lack of insulation. The older apartments where most people live were not built with cold in mind. They were built with an open floor plan and lots of windows that let the breeze in during the hot and long summers and mild springs. On top of that, bad insulation from old construction means the walls retain the cold, and it just sits there for days on end. In fact, late at night if you touch the wall behind our bedroom you will discover that is feels about ten degrees colder than the rest of the room, as if the wall had spent some time in the fridge. Add to that the lack of central heating, and the result is that Tel Avivians end up using the poorly-conceived heat feature on the air-conditioner and standalone electric heaters to stay warm. Everyone here can tell you: they are no match for the frigid walls and breezy hallways.
And yet, winter here is short, this is a #FirstWorldProblem, the fuzzy slippersI bought feel soft on my feet, and the feeling of huddling by the electric heater is something akin to the cozyness of huddling by a fireplace, though I'll grant you it isn't quite as scenic. The streets do look pretty sometimes in the rain and, most importantly, I know what gear I will be needing to purchase to make next winter as warm and cozy as can be.
In case you spend a summer in Tel Aviv, here's the list of my recommendation for what you need to survive winter in Tel Aviv. But more than anything, the greatest tool to survive winter is knowing it is short and, come April, I'll be back to lounging on the beach till late November.

Tel Aviv Winter Survival Guide (clockwise from top left):
1. Apartment in new TLV construction with insulated walls.
2. Fuzzy slippers.
3. Electric water boiler or "kumkum."
4. Extra pairs of long, preferably colorful socks.
5. Warm tea. Apple cider, cinnamon and ginger are great options.
6. Rain boots.
7. Insulated hot water bottle.
8. Radiator.
9. Umbrella.
10. Heavy duty waterproof raincoat (like the North Face pictured here).