October in Trieste - stylish solution for rain&wind

If you don’t own a really excellent raincoat, that is what I would invest in. Something that has an inner liner that you can remove would be great. I had one from Boden for years till I wore it out, but not sure if they currently sell a similar model. I have one that is north face with a removable light puffer, but I think you want something less sporty, more like a trench or a Macintosh. I don’t think you’ll need a puffer in early October.

I have a light raincoat from Athleta that I find attractive, you might check there to see if they have a medium weight one.

I take a trenchcoat on every trip to Europe and feel that it's versatile. Past versions have had a zipout liner, which is a good option. My current version is a tightly woven cotton, no zipout lining, and it has served me well even when the temps are in the high 30s (F). It's water resistant, not waterproof, but if it was pouring buckets I would be seeking shelter indoors anyway. It's worked just fine even in heavy rain (while also having an umbrella). My version does not have a hood, which I personally don't like anyway, so I have a matching bucket hat that I keep in my pocket if it looks like rain.

I will say, wherever I've been in Europe, even in big cities like Milan or Paris, I'm not seeing many trenchcoats. I see many, many more casual jackets (but keep in mind, many of those people are locals who may have a nicer coat at home).

While I'm a trenchcoat fan, given your planned itinerary, a rain jacket and a puffer coat would work well too. My spouse and I giggle at the temperature (that seem plenty warm to us) that we see Italians in particular wearing their puffer coats. If you want to blend in with the locals, probably the raincoat and/or puffer coat would do that..

Technical gear is having a fashion moment so you can wear outdoor clothing in the city now and look perfectly stylish - half of East London are wearing Salomon shoes to go for no more than a coffee. You will never find ‘fashion’ clothing that functions as well as proper outdoor clothing and once you go down that route you’re never looking back.

If price isn't a factor you might look at Protected Species, based in the UK, for their style and function. I have the City Walker style from several years ago. It is fully wind and rainproof with an excellent hood. I wore it in torrential rain in Scotland hiking as well in various cities. It's roomy enough for a sweater under, if the weather is cold.
It's beautifully crafted and washes well.
I bought their fleece- lined jacket, too, for the PNW but it runs large and doesn't "read" stylish, more like a regular parka.

Husband and I both have 3 in 1 jackets from Columbia. While I am not completely enamored of having “Columbia” stitched across the jacket, for us the pros of the jacket for outweigh the cons. It is water proof with a zip out lining. We put the zip out lining in a compression cube and have an extra pillow for our lower backs during the flight. Keeping the lining out we have a rain jacket or a light weight coat, and with the lining in, we have a very warm coat. They are not dressy but they are very utilitarian and work well for us.
We compared prices between Amazon and direct from Columbia and at the time (last year) purchased directly from Columbia. Be sure and read the reviews, I had to purchase mine in a smaller size; even accounting for possible layers and the lining in the winter, I had to size down.

Athleta has attractive and packable raincoats. I bought one with a little extra room so I can wear a vest or sweater with it. The perfect solution for changeable October weather.

I’ll add another Athleta recommendation for a rain jacket. The one I bring is mid thigh and not too technical looking. It is lightweight but I wear it on the plane. I do bring a Quince puffer to layer under. The puffer makes a nice pillow on occasion!
I see my specific Athleta coat is sold out this year but they have similar.

You didn’t mention budget, but brands like LL Bean, Eddie Bauer, etc., should offer something in the 150 range.
These seem to have potential for that time of year:
https://www.kuhl.com/kuhl/womens/outerwear/ws-stretch-voyagr-trench/?color=raisin
https://www.kohls.com/product/prd-7054071/womens-bgsd-amelia-waterproof-hooded-zip-out-lined-parka-coat.jsp?skuid=72413263&CID=seo_offers&utm_campaign=SAG&utm_medium=organic&utm_source=google&utm_product=72413263

Thank you so much for all your thoughtful replies.

I found that unless you go with a 3-in-1 type garment it is hard to pack one jacket to do it all - different temps, rain, wind.

I also found that waterproof, lightweight and packable come with a price! On the other hand, this is my last year working so if I'm not gonna invest now, then when?

Also found that more urban/dressy means longer (not a bomber length) and to be realistic i usually wear short jackets at home. I do like the look of a trench but it may not be for me.

I haven't made a selection yet, I have gone a bit crazy ordering, comparing and returning. I narrowed it down to 2 long jackets from Mountain Hardwear and Rains.
BTW, currently Athleta only has their bestseller waterproof long jacket in black and i want to get away from black.

Thanks again! 😊

As people have already mentioned, puffer coats / jackets (piumini) are ubiquitous among Italians as soon as the weather turns cool. I had an interesting conversation with a couple of Italians at the flagship Uniqlo store in NYC. We were standing in front of a wall display of puffer coats and I was drawn to this beautiful jewel tone blue jacket. But I asked them what color an Italian would choose. They pointed to the neutrals - putty, gray, white, black.

Hi, again, Adriana- glad you received such helpful advice. Congratulations on your upcoming retirement and I'm writing again because I did the same: purchased some much more expensive clothes with the intent of using them for more travel.
My Protected Species packs in my carryon suitcase laid flat on the bottom with packing cubes on top. Or, wear it on the plane and I put heavy stuff in the pockets if there's weight restrictions. It has a drawcord at the bottom I only recently discovered (with a mirror, vs hiking in a downpour!) looks much more bomber jacket stylish when cinched. I have worn a puffer vest under it as well as a fairly heavy sweater.
But, if you want zippered liners I also splurged on a Fjallraven style. It's long (mid shin) and has a very warm liner I wore in winter in Montreal. The outer shell is water and windproof and the hood is great. (I don't wear it that much in real life because the longer trench length feels cumbersome with a really active lifestyle.)
Happy shopping!

After lots of searching I found the Protected Species site. Very nice jackets, steeper than most at $300. However no use to me as they specifically say they don't ship to the US. Did you get your jacket in Europe?

If you only want one layer to save on space…just do exactly that.
Then, if you find it’s chilly in Italy, head for the nearest street market selling clothing and buy a cardigan, thin puffer jacket or something you can layer under your water resistant outer coat.
No one sees it but you, but you’ll be warm.
A couple of years ago it got a little cold in Ravenna for a couple of days.
I bought an inexpensive thin puffer jacket in the local outdoor market that fit under my rain jacket.
I donated it on the last day of my trip.
Saves carrying it home.

I would suggest a stylish leather jacket and a packable rain jacket (covering the hips to mid-thigh). I usually take a small umbrella, too though not so good in the wind. The rain jacket can go over the leather jacket or over a heavy sweater/sweatshirt. That is my usual solution.

Welcome to the forum. I am so glad you came and asked your questions.

I have to confess once I saw "stylish", I realized I may not have much to offer since I definitely pack for function. So, if you don't mind a "functional" response, I say layer, layer, layer. Forget a heavy 3 in 1 jacket. If you have a nice sweater that can serve as your warmth layer, then a good waterproof rain jacket with a hood will make your trip much nicer. It will cut both wind and rain. I wear Columbia waterproof rain coats (they do come in different lengths) and they work really well for me. Umbrellas are subject to the wind and if you really need to use one, most hotels have loaner umbrellas so no need to pack.

I was caught in a downpour in Dubrovnik once where I was up on the walls and exiting was problematic. I have never been so drenched. At that moment the last thing I was thinking of was stylish......

You all are so incredibly sweet, thanks again!

SJ and Carol now retired: I agree, layering is the answer!

Sharon M: I love leather but I seem to be going through a permanent hot flash (🙄) so in the summertime I have to go a little lighter. I was thinking a lighter weight denim trucker jacket.

Accidental Southerner: Thank you for the colors comment. I am trying to exert self restraint and go neutral!