I was given that one as a gift. I’ve used it once or twice.
My current preference is to use 2-3 of the Clinique gift-wth-purchase bags. I use one for daily makeup, one for extras (like the Tide Pen, etc). And the third is for prescription meds.
These are fairly easy to tuck in my suitcase or backpack as carryons.
I bring one statement necklace and 2 pairs of long earrings only when travel includes meetings and events. They are not expensive but I sourced them at art stores and they look interesting. They make some very plain black outfits look more fancy and take less space than adding outfits.
I only travel with my fabulous costume/lab bling. The expensive stuff stays home. I have some truly gorgeous travel jewelry that is indistinguishable from the expensive stuff. I take whatever I need for each outfit I pack, casual or dressy, and don’t worry about losing it though I’ve never lost anything. It all goes into a small pouch in my underseat cosmetics bag.
Tip: For those who don’t want to travel with expensive stones, check out moissanite, next in hardness to diamond, rarer than diamond, with a higher refractive value than diamond for more fire/sparkle at a tiny fraction of the cost of even lab diamonds. Comes in many colors.
I used to take gold gold jewelry and white gold jewelry, and a fair amount of it. At some point I got a necklace and earrings that are gold gold and silver, and can be worn with almost everything. Sometimes I will take them and one more necklace and one more set of earrings, but usually I just take them. I have my wedding set plus sometimes another ring, and my Apple Watch. If I’m going someplace I might want my “fancy” watch I’ll take it too.
So the moral of this story seems to be “pack your clothes like you would your jewelry- minimal! Something that goes with everything! 
I have that bag and I love it. I really appreciate the ability to hang it up which helps when there isn’t much counter space.
I double check my meds and my phone and then try not to worry about it. If I forget something there will be stores where I’m going.
Short trip–morning of toss stuff in back pack. One change of clothes per day and extra pair of underwear. I have a travel to go bag of toiletries that I double check.
Longer trips-- I tend to plan and pack the day before. We had a 20 day trip to the UK which included 11 walking days where our bag was moved to our next location each day. It meant we had a 18 kg weight limit. This definitely led to some serious planning-- including figuring out where we could get laundry done.
This is generally my approach - I include an extra pair of socks also!
Same, but I don’t wear much jewelry to begin with. I also don’t want to keep track of it. I recently misplaced a bracelet stack (I know it’s somewhere in my home). I have my Catholic daughters appealing to St. Anthony on my behalf 
That’s a LOT of clothes for a long trip. We were gone for five weeks, and had laundry facilities for most of the trip. If each of us had taken one change of clothes per day, we would have needed a LOT of luggage, and that wasn’t happening.
I always pack a change of clothes and underwear in my carry on after my luggage not making the trip when I did.
To be clear that method is only for short (7 days or less). For longer trips, I typically aim for a weeks worth or enough to last between laundry days. On our last trip, I knew 3 of our B&Bs had laundry which made planning easy.
I have never gone on a trip longer than a week and have never done laundry on a trip (besides hand washing a stain in a sink so it wouldn’t set.) If a trip were longer, I guess I would figure out the number of days between laundry stops and pack for the longest.
To be safe when travelling via plane, I always have the essentials in my carryon - PJs, a couple of underwear and socks, a few shirts, etc. so I can go a few days without my checked bag.
When travelling with other family members, we use packing cubes to put a couple of days of clothes in the other person’s checked bag. This way if one bag is lost, everybody still has some clothes.
We generally will not pack more than a week’s worth of clothes. I really don’t like the idea of spending my vacation time doing laundry - it’s fine if we have in-unit washer/ dryers, but I have better things to do on my vacation to wait around at hotel laundromats to make sure nobody dumps your clothing out the second the cycle is done (yes, I speak from experience). For longer trips without our own facilities we will therefore make use of wash/dry/fold services. There are some clothing items I wouldn’t hand over for that but so far, despite my trepidation sometimes, we’ve always gotten everything back and nothing has been messed up.
I’ve been on the road for up to three weeks without doing laundry or packing more than a roller bag. I will wear bottoms (jeans, khakis, shorts/denim skirt) at least three times and tops at least twice. I’m never doing anything to produce a bead of sweat, so enough clean underwear for each day and a daily shower stretch my color-coordinated palette (navy, black, tan, white) of three or four bottoms, six or seven tops, two sleep tees, and a light jacket beyond the need for travel laundering. We are leaving next week on a ten-day driving trip to Michigan for my 50th HS reunion. For this trip, I will be adding cocktail attire/shawl/shoes/jewelry that will still fit comfortably in my roller bag. No packing cubes.
As much as I hated all those years of business travel, it did teach me how to pack. Doing laundry on the road is a big no for me. And no checked luggage. Ever.
Here’s an example of what packing for a previous seven-day road trip looked like for me (underwear, sleep tees, travel purse, umbrella, and light jacket already packed in the roller bag, cosmetics/toiletries in the smaller bag):
Amen!
I’ve also done 4 weeks with just a roller bag, a backpack personal item, and no laundry. Although I’ve been known to hand wash things in the sink if something gets stained. I travel with a Tide stick and bring a travel bottle of fabreeze fabric refresher. I spray things after wearing and let them air out overnight on a hanger.
Understanding that some lodging has laundry facilities or that you need to potentially find some, a consideration is also what type of vacation you are on. A very active vacation where you are hiking daily or very physically active - you’re not going to be rewearing your clothing multiple times without washing! Also may make a difference in the type and amount of footwear one needs.
One size does not fit all packing for a vacation.
…does not describe a vacation to me. 
Totally agree.
How did I know that would be your response?? 
For many it absolutely is their vacation! Just like I can’t imagine packing fancy shoes/dresses for a vacation (do I even own any? No.), I know that others have different needs - and desires - than I would have on the vacation I choose to take.
