Packing for 3 weeks, multi destination help please.

[BeCoolYolande]

I'm 5ft 2, size 10, mid 40s.
Typical hourglass, very busty.
HoC summer, blues always look good. I'm happy with that but I'd like to look at other colours.
My style is simple and pared back, bold patterns swamp me.
I definitely feel the cold, especially on flights. We'll shop while we're there but don't want to be tied to having to do it.
I'm looking for investment pieces that will be worn again and again.

I love dresses, jeans and skirts are fine, trousers can be a minefield because of the leg length.
I'd prefer sleeves as sleeveless tops often accentuate my bust.
The current tunics and midi dresses are a personal hell. They're inevitably the wrong length or the lack of waist makes me look huge.

It's a big birthday for DH next year.
We're flying in to Toronto, going to Niagara, Chicago, San Francisco and Palm Springs for 3 weeks from July.

It's early to plan but I'm scouting the sales.

I've got most things already I think, I'll need clothes for:
Travelling, sightseeing, good restaurants, naice hotels, blues clubs. I'm aiming to look chic among the city commuters, not dowdy.
Lots of pieces will have to be dressed up or down. For the blues clubs I'm after sultry noir, rather than Vegas hen-do.

One thing I would like is a good quality shirt dress, I'll probably need a new jacket.

The weather could/will be everything from breezy summer drizzle to desert heat.

Any suggestions or US/multi trip travel tips are very appreciated.
TIA

Comfort is a priority on that kind of trip.
I know the US well and San Fran is potentially chilly in July. Palm Springs will be sweltering.

That's what I thought Fochit, Chicago also has the potential to be chilly and drizzly.

Comfort, I get it. It's comfort with style that's more tricky to pull off.

The problem I find with dresses is that you can only really get a maximum of a couple of wears before they need washing. Separates more practical for mixing up outfits. Skirts, shorts and trousers can be worn multiple times before they need washing.
When we travel I try to book somewhere mid trip with a washing machine.

Suggest a cashmere travel wrap for the plane that can double as a scarf/throw on cooler evenings. I have one from the travel wrap company in Scotland and it packs down tiny in its own bag. Not cheap tho.

this article might help. I think you need to take trousers x 2 dress x 2 skirts/shirts x 2 long sleeve shirts, t shirts, wrap/ cardigan and a jumper. Trainers and Birkenstock's and if you have room smarter sandals for going 'out'. I'm about you height and I have successfully bought 2 pairs of Baukjen cotton casual trousers which have roll up legs and they look good on me. There's a sale on. Their jeans also fine for me bizarrely

A couple of years ago we did several Asian destinations + Melbourne in their Winter. I packed several lightweight summer dresses, midi skirts & t shirts. One pair of jeans. One heavy cotton jumper - one large cashmere wrap. One lightweight puffer & one smart sandals, one trainers & walking sandals. Hot weather is not a problem as light cotton rolls up very small. Maybe you can take one smart dress for evening in addition.
I'm also 5 ft 3 and suit blues. Monsoon in brilliant for summer clothes and midi skirts are so much easier than dresses. But saying that my style is bohemian hippie aka Free People and yours may be very different. I travel in joggers and a t shirt plus a Cashmere jumper/ wrap. A Cotton Cashmere mix would be very comfy or Cos usually have some cool jogger style trousers . One thing is I always wear dark colours having have several incidences of drinks spilling on me ( usually my kids).

For a wrap I recommend a pashmina ring shawl. Beautiful quality, very fine pure cashmere that folds up to nothing but soft and warm for flights

Huge range of colours

www.mypashmina.co.uk/product-category/pashminas/cashmere-ring-shawls/

Thank you for your tips.
My sticking point is that I think we'll be traveling through a lot of spring/summer changeable weather to compare it to British climate.

By coincidence I've been looking for separates today but there's the leg length trouble and finding pieces that will suit me. Tops I have but bottoms are another story. I'll check out Baujken trousers.

I've been going through my wardrobe and I don't need to buy much more, just some versatile items and pieces that finish off an outfit. The truth is that I prefer dresses and they look better on me.

For long haul travelling I always wear a sweatshirt with layers and jeans or smart joggers with a pashmina. I think I may be ok with t-shirt dress for the shorter journeys.

We'll be staying for at least 3 nights at three of our hotels and I'm hoping they have good laundry facilities, that would be a big help.

I like Free People too, very much. Also Anthropologie, French Connection, Sezane, Reiss, some Urban Outfitters. Hobbs and L K Bennett for workwear.

I'm going to spend some time taking out a piece of clothing and making up as many outfits as I can with it and go from there. I'm not very good at putting outfits together in my head.

I think that’s key really.

If something only goes with one or two others items then it’s not worth taking.

Layers are good

Interesting challenge! Random thoughts that I’d probably base my decisions on:

Jeans are an obvious choice because they’re comfortable at any temperature up to about 20c, go with everything, travel easily and can be worn several times between washes.
Stretchy fitted tops can go under other things for warmth, take up very little room and should wash pretty easily in a bathroom sink. Same with leggings.
Maxi dresses can have leggings underneath (wouldn’t be visible) and big jumpers on top for warmth, and be cool on their own in hot weather. And are comfy on planes.
You could do the same with shirt/tunic-type dresses or tshirt dresses.
A blazer with a big blanket scarf is nearly as warm as a coat, but easier to pack and smarter.
Lightweight converse-type shoes can be made much warmer with sheepskin insoles.
Avoid white because you can wear it a maximum of two times before it needs a wash, and it won’t wash properly in a sink.

@BeCoolYolande you could think about a style app which you can put in some of your items and they come up with outfits from the combinations? People do this I know. I do not!

Do you know of any good style apps Sooverthemill?

@BeCoolYolande most people seem to use style book look on the outfit of the day thread I think people on there use another one too

I'll take a look, thank you