I've been lurking but your post makes me unlurk long enough to reply! This is one of my favorite topics, since taking on a job with 50% travel about 3 years ago.
My travel takes me everywhere in North America, all different climates. I've also learned how to pack for vacation travel to beach or Europe. And while our house was being renovated, I lived out of two suitcases for 9 months (one packed with business clothes, and one with leisure wear), while traveling non-stop to escape the mess and noise. You can go back in my posting history and see more posts I've made on this topic.
I am not like Angie however in that my primary travel goal is traveling LIGHT. Due to back problems etc I was determined to learn how to pack minimally, and all in carry-on. One blogger I really love for travel capsule tips is Unefemme.net. (I also like her site as she's about my height, similar build, similar age -- so I'm finding her clothing recommendations generally work well for me).
You asked about Eileen Fisher. I have become a huge fan, and some of my key travel pieces are EF. This includes the slim crepe ankle pants. They travel beautifully! And work well even in hot climates. I also like EF skirted leggings, though I wouldn't bring those for a business trip. I like them because they can be easily layered with fleece leggings underneath, and they are dressier/more modest than regular leggings. I also have a couple of EF cardigans that are lightweight, don't pill, pack well, and keep me warm.
I am short however. I wear EF petites. Any brand reco's below, are based on my petite experience, and I know you are tall so your mileage will probably vary. Also realize that because I'm so short, yes I can fit all of the below in my bag, because, well, my clothes are smaller to begin with....
MY METHOD
1. I start with the shoes.
I try and limit myself to just 3 pairs, one on my feet (the bulkiest) and two in the bag. It goes without saying that all shoes must be road-tested and comfortable for hours of walking. I pack two flats (one more casual and one more dressy) and one pair of modest-height heels. That said, sometimes if I pack light elsewhere, I can squeeze in another pair of shoes, if they aren't too bulky. Did that on my last trip. Shoes are THE most important thing you will pack, as they can make or break your trip.
Generally I find packing black shoes is the best strategy as they'll go with anything, but I don't always follow this and will take along one pair of more interesting, non-black shoes. My last trip for example I took white mule loafers. Sometimes I take leopard booties. I stick to "neutrals" and consider white, animal print, and metallic all neutrals. I also often toss in a pair of J Crew metallic thongs, but they take up very little space, so don't really count in my mind. They are great to have even on non-beach vacations as you can wear them to the pool, around the hotel, and if your feet swell you have something you can still wear. Also I bring moleskin and blister packs in my toiletry kit.
2. I pack 2-3 bottoms depending on length of trip.
Almost always, I bring black 5 pocket ponte knit LOFT leggings, and the EF slim crepe ankle pants in black. The 3rd pair could be jeans. Or skirted leggings. I don't pack skirts but I don't wear skirts.
3. I pack tops that go with the pants next.
This can vary depending on the climate and whether business or leisure. I pack one per day, plus 1-2 extra. I find that silky/synthetic blouses take up less room than cotton tees, and also wash out in the sink overnight. But I will take along a tee or two (white or black or striped). I also pack an EF silk camisole for layering.
4. I bring 2-3 toppers.
One I wear one the plane, and two in the bag. This could be a blazer, a denim jacket, an army jacket, a leather jacket, cardigans. This does not include outerwear like a trench or puffer -- I wear that on the plane. I prefer cardigans to pullovers because I find they are more versatile for layering.
5. I pack silk long johns.
They are super light weight and take up little space in the bag. I use them as sleepwear. I also use them to layer under clothes if it's colder than expected. They rinse out in the sink and dry overnight. I also tuck all my jewelry inside them, to protect my jewelry.
6. I bring a couple of scarves.
I wear one on the plane and tuck another in the bag. Scarves not only provide warmth but add interest to my outfits.
7. I bring one dress.
Call it the LBD, but it needn't be black. A simple dress that can be dressed up or down with change of footwear and accessories.
8. I bring an interesting flat clutch.
Instead of a handbag, I use flat clutches which can be tucked into my carry-on, so I have only two bags (carry-on and carry-on roller bag). I make this piece interesting - pop of color, animal print, etc -- so that it works for dressing up or down. That said lately I've added a small cross-body to my travel capsule, which is lots more casual but very handy for travel. Still small enough to tuck inside a bag.
9. I bring a reusable shopping bag.
The kind that rolls up small. This can be used for shopping but also makes a handy beach bag.
10. Toiletries: keep them in check.
I find toiletries can take up a lot of room if you aren't careful. I invested in a set of travel sized containers, tiny make-up pots, a small pill box for my meds and vitamins, and a Quip toothbrush. I keep my toiletries permanently packed and ready to go, refilling after each trip. Also I pack them in an Eagle Creek nylon pouch. After trial and error, I find this works best, as the soft sides allow the toiletries to kind of spread out and make use of excess nooks and crannies in the bag, rather than a hard-sided kit which just takes up unnecessary space.
11. I use Eagle Creek Pack-It system.
Highly recommend!! I put my shoes in the shoe bags. My toiletries in a large pouch. Silk long johns & jewelry in a small pouch. Another pouch for undies and bras, and a compression pouch for any tees or leggings (rolled). And use the flat fold-it thing a ma bobby for pants and tops, this goes on top of everything else. I also use a pouch to corral beach wear - bathing suit, hat, cover-up.
12. Undies.
I bring one per day plus 1 extra, and two bras (nude and black). I did invest in some travel undies but I don't like them as much. If I'm traveling for more than a week, then I just bring a week's worth and plan on doing laundry or washing out in the sink. Oh and socks of course! I prefer traveling in shoes I can wear socks with, as it reduces chance of blisters. I also bring socks on beach trips, because my feet get cold at night.
13. Bags
I have a Briggs and Reilly carryon that is non-descript, light-weight black nylon, with a sleeve so it slides on over the luggage. No it's not fashionable but it fits a ton of stuff. I pack my laptop and electronics in it, the clutch, a book to read, and I still have room leftover for a topper or two and scarves. My roller bag is Vitronix and it's been going strong for 3 years despite lots of abuse.
14. I do often end up with a color theme.
Not saying I aim for one, it just tends to work out that way: Black + white + a color. My last trip the color was blue. Prior trips the color was red. Color themes tend to happen naturally when I decide which scarf I'm going to bring. Does this top go with that scarf?
15. Beware items that take up too much room.
Sweatshirts. Sweat pants. Pajamas. Robes. Bulky shoes. Jeans. These are the packing killers, as they take up too much space. Even cotton tops take up a lot of space, compared to blouses. And yes, sneakers. If you want to bring these things, wear them on the plane!! And it is quite okay to wear the same travel outfit to and from.
15. Map it all out, and try everything on.
I use PPT to map it all out visually before I start packing. I walk through my trip and what events and occasions I need to dress for. I watch the weather closely. I audit what kind of underwear, belts, bras, socks I need for each outfit to make sure I don't forget something. I play around with it all on virtual paper first, making outfits. Then when it's time to pack I try everything on to make sure it still fits and I feel excited to wear it. I often wind up making last minute tweaks. When I get home, I go back to my PPT record and note what I actually wore, and what I didn't, for future reference.
16. Account for bloat.
I don't know about you, but traveling makes me bloat. Just being on an airplane, I'll get dehydrated and this leads to water retention. Not to mention eating out. So I value stretchy forgiving clothes, over tight and structured.
17. Warm-weather trips.
... you can pack a lot more because the clothes are lighter weight and skimpier! Always bring 2 bathing suits for beach trips. Do go ahead and pack more, as you will sweat more. Also you're probably more likely to be packing cotton, which as I said is bulky. Bring along a zip-loc pouch, as you may be packing a wet bathing suit on the way home. Don't pack a towel, as you can surely get one wherever you are at. Don't forget a hat and sun bloc, as sunburn is no fun. Often we just buy sunscreen when we arrive, since I go through it like crazy.
18. TSA-pre!!! Do it!
You don't have to take off your belt or shoes, and you don't have to pull out a 3-2-1 bag. You breeze right through security. If you travel a lot, it's worth it.
19. Cold weather trips.
A packable puffer is worth it. Bring tall boots, and wear them on your feet. Those silk long johns will be a god-send, as will some fleece leggings, and a warm scarf, hat, and gloves.
20. Rainy weather trips.
Packable umbrella, crushy rain hat, and waterproof trench. Do not bring suede shoes. Bring shoes that won't leak if you step in a puddle. Also, consider packing dresses/skirts, rather than pants, as wet pants or hems are no fun.