I swap the trolley and cart bag for a carry bag in winter I got the hybrid 14 earlier in the year and up in Scotland I pack golf mits,Tammy,snood these are usually on by the second hole oh and spare socks.....

For winter, I've moved down to a StaDry stand bag but have stuck with the same bats for now with the exception of the 4 iron, which is in the summer bag. Will probably cut down as the winter progresses
Have taken out the sprays, plasters & potions that crept in over the summer and cut down on tees & extra pitch tools. I've changed over to Velocity & some yellow AVX balls and put those odds & sods balls - those mongrels you leave in the bag over the summer - into the practice bag. Additions to the winter bag consist of an old Titleist bobble hat (I hate hats & know I look a beggar in it, but... needs must) Titleist winter mitts & the new FJ neck warmer (the one with the FJ logo all over).
If it ever stops raining, I'm ready to go!
JT

I actually go the other way, change from my carry bag to trolley bag. Allows me to stuff loads of additional clothes in the bag and not worry about the weight. Playing in Scotland, Hat, snood, mitts, are a must but I like having a few different tops (including sleeveless) so I can layer up and down as required.

I actually love playing early on a crisp fresh day with woolly hat on.....plenty over next few months ahead. Photo from a couple of years ago

Happy golfing folks

Bob,
My course has banned buggies & "requested/suggested" that everyone carries - at least until the floodwater subsides... so, with a following wind, that should be about May.
I morph into the michelin man before I step out of the locker room so it's usually a fairly empty bag.
JT

As I use a trolley all year I'll swap between the normal and stadry depending on the weather or if I think there's a trolley ban.

All the summer stuff is out, insect repellant and cool towel replaced by hand warmer and beanie hat.

Also the Permasoft glove is replaced by weathersoft.

I might switch back from Pro v1 to AVX just for the winter.

Ant

Also I fill my water bottle (flask) with hot (not boiling) water as a sip from it helps keep the chill out.

Got me some mitts. Loving them on the range to keep my fingers warm.

+1 for how good the mitts are Alex..

The lining is soft and warm, the outside wind and waterproof with Stadry material and each palm has a slot to pop in some hand warming pouches.

We have the newer style with the bold Titleist logo on the cuff is an improvement over the placement of the logo on the back of the hand like the previous model.

Have just ordered a new pair of Titleist mitts on the basis that I can't find the right hand to my previous pair.
I've lost countless right hand mitts over the years... Perhaps I should string them together and run them through my top layer - like they do with small kids.
JT

or by the Titleist fleece lined hand warmer sleeve ….

Ant,
Never thought of that....
JT

Just put my trolley into hibernation and moved over to my 5up Stand Bag.
It has plenty of space for winter gloves, Titleist mittens, snood and 2 beanie hats.

Not a huge fan of winter golf but this winter (subject to weather not closing my course) I plan to play a bit more

I usually have my waterproofs, bobble hat, mitts, hand warmers and rain gloves in case they’re needed...oh and an umbrella.
I don’t have a snood but I think it’s definitely something I’m going to invest in as I hate the cold wind going in the collar of the top/jacket and giving that chill down your back.
Also occasionally a flask of tea or soup if it’s just above freezing to warm you up mid round.

As soon as the clocks change my club moves into 14 hole comps, so the Powakaddy goes away and the stand bag comes out, and a couple of clubs taken out, usually a fairway wood and one of the wedges. A nice warm bobble hat and pair of mitts also will be making an appearance very soon!

Kitted out with a 2018 Stadry stand bag and looking to add a 2019 Stadry cart bag in black/red.

Also use a number of my Titleist winter accessories when playing, all highly recommended for winter play.. Titleist bobble hat, Stadry bucket hat, Stadry cap, Titleist mitts & a Titleist snood.

I have a very similar set up, I have a selection of bobble hats to match my outfits. You have to look good on the course.

I also have a handwarmer, as per the ryder cup ones, but I only used it once last year., plus a pair of the FJ winter gloves.

Look like it will all be coming out this weekend.

Some good suggestions on here. I also carry a bradel with me for those frosty morning tee beds.

I use a bradel to help get my tees into those cold frosty morning tee beds.