I'd start with the shoes first. It's going to be chilly in October, so I'd pack shoes you can wear with socks. You'll be walking a lot so pack mostly flats, with maybe one high heel option for going out. If it were me I'd probably wear a pair of tall boots on the plane, and pack a pair of dressy loafers, a pair of fashionable sneakers, and a pair of heels.
Then I'd go over to Vivienne Files, which I have been reading through lately, and take inspiration and packing tips from her.
Okay let's see if I learned anything from all the reading -- and travel -- I've been doing lately! If it were me and I was packing for just such a trip, here's what I'd pack - see pic....
Theme: neutrals in black/grey/cream + accents in cranberry/blush/red shades. For accessories I'd keep it to black/cognac/gold.
It's probably too much to fit in an international carry on though! So I might start with this and pare it down, if you can't or don't plan to check your bag.
For my pretend trip, I'd wear the black long cardigan, white tee, and black leggings (Theory - substantial weight) tucked into tall boots on the plane. These leggings are pull on but styled like 5-pocket jeans, so they double as regular pants. I've chosen just one coat here - a packable puffer - but depending on the weather nearer the trip, I might instead take my Burberry trench, which I'd wear on the plane.
Shoes:
I'd bring flat or wedge boots, not heeled - do not have a picture, so imagine. For heels I'd pack the leopard booties, because my feet get cold, and I can wear them with socks, which also prevents blisters, and I can actually walk quite a lot in these so they play double duty. I'd want a pair of bronze or cognac flats instead of these snakeskin flats, but I don't have those in my closet so I am working with what I've got here. But bronze or cognac flats would be more versatile, I think. The black sneakers shown here maybe aren't the most fashionable but I know I can walk forever in them, and they look fine with all sorts of pants.
Accessories:
I'd add a few scarves (not shown) - as many as I could fit - in the accent colors.
I'd debate extensively between a cross body bag, or a roomier handbag - here I'm showing a cross body, but I do like having a roomier bag for travel, because I can stuff my scarf or cardigan inside it. It would probably depend on whether I'm going with carry on or checking my bag. If carry on, then the cross body actually fits inside my second piece of carry-on.
I'd pack a clutch inside my luggage; I always do - useful to organize items, and nice to have a second bag handy.
I've only included one belt because pretty much everything I'm packing will not show off the belt; it's purpose is just to hold my pants up. I've done this deliberately because if I'm eating and drinking a lot on this trip, I am likely not going to want to tuck anything... belts don't take up too much room so I could add another.
Clothing:
I may actually skip the jeans entirely because I like to be comfortable when I travel, and jeans take up a lot of room. The BR Sloans I've shown here (http://bananarepublic.gap.com/.....=970102002) go with so much, and are way more comfy than jeans. The subtle B&W pattern would not show dirt either. But here I've settled on dark wash skinny jeans because they can tuck into tall boots. Straight leg would be my other choice. I've not chosen any wide leg dress slacks, because they would only go with the leopard heeled booties, and require a different type of top too. Basically I've chosen a silouhette here of fluid/loose over slim, so it all works together.
I've packed extra sweaters, which also take up a lot of room, because I prefer them, however, I'd likely pare down in this area if I couldn't get it all to fit in the bag. (Packing tip: Roll everything!). I haven't packed too many cotton tees because I find the blouses more interesting and they can be layered just as easily. Also all the blouses I've chosen would rinse out in a hotel bathroom quite easily and drip-dry by the morning. If I could find the perfect white tee in a travel-friendly material that can be washed in a hotel sink, that is exactly what I'd take. I just don't find cotton layering tees all that travel-friendly.
I'd bring one dress, because I love dresses. I've chosen a dolman sleeve sweater dress here, with forgiving waist (since I assume I'll be eating a lot on this trip!), but now that I think of it, it's probably too bulky, so I'd probably go with a packing-friendly jersey instead.
I did not pack any blazers/suit jackets because I'm assuming this is vacation, not for business. If it was a business trip, I'd swap out the grey cardigan with a charcoal blazer.
I did not pack any leather jackets because they take up too much room and a knee-length coat is much more versatile. However, I might manage to tuck in my black pleather cropped moto, which takes up little room and acts as an excellent layering piece, especially over a dress.
I'd probably obsess endlessly about which cream sweater to bring for layering: this v-neck pullover, a zip cardigan, or a boyfriend cardigan...
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