I pack both fancy dresses and hiking clothes! It helps that we mostly vacation in warmer places like Hawaii or San Diego! 
Because that means the clothes are lightweight and pack small. No need for heavy fleece etc. I’m researching and planning another trip like that as we speak. I never pack swim suits into a carryon because there is always a minuscule possibility that it can become checked luggage and not make it to the destination at the same time as us. Swimsuits are the hardest to replace clothing items!
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When we go on active vacations (cycling trips that may also include hiking, kayaking, rafting, etc.) we need both cycling clothes AND regular clothes for many days. AND cycling shorts won’t always dry overnight hanging in a room, AND we often change hotels every day or so. My H learned from experience when we were in New Zealand for 28 days that men’s cotton unders don’t always dry overnight either. NOW he has his “fancy travel underwear.”
We did manage to go on a 12ish day trip to Venice, the Dolomites (for 6 days of cycling”) and on to Verona with just carry on backpacks (40L each) and sharing 1 26 inch suitcase. BUT, our preferred method of packing involves us each taking a 30 inch wheeled duffle (checked) and just light backpacks on board.
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We went for a one month trip to NYC, Scandinavia and Tokyo. I managed to fit my big medical equipment and all the cords & batteries (which took up 1/2 or more of my carryon suitcase) plus ONE backpack. I believe we may have done a tiny bit of laundry and some handwashing. Otherwise, was able to fit all we needed. H had his own carry on suitcase & backpack.
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How I pack for a trip:
long weekend type of trip:
- all clothes & toiletries go into a Biaggi Runway Hybrid Expandable Underseater rolling bag
- everything else goes into a Bento bag
Longer trips:
- I try never to check any luggage. Only do carry on.
- Used a work house of an American Tourister R2D2 suitcase for over 8 years. That one has now retired for a Travelpro rolling carry on bag which has an 38 L capacity. Weighs ~5.1-5.5 lb empty. Clothes & shoes go into that plus some toiletries.
- Other stuff goes into my Bento bag, which holds 24 L & weights 2.78 lb empty. I also bring a purse, but for plane travel, I put the purse in the Bento bag. Liquid toiletries get put in the designated zip-up toiletry pouch/bag thingy that comes with the Bento bag.
- Small chargers, charging cords + 2 small USB-rechargeable batteries go into the designated electronics bag thingy that comes with the Bento bag (and it has its own slot in the bag to stash it in).
- undergarments & socks - I put these all together in a small compression packing cube.
- pants & 1 set of PJs (usually a T-shirt & shorts) - these go in a larger compression packing cube. If it’s a 7-day trip, I try to pack 7 changes of clothes but I usually just bring 5 and plan on washing clothes on day 4.
- tops/shirts - these go in their own compression packing cube.
- big lightweight scarf/sarong - I bring one regardless of what time of year I travel. In colder months, it’s a scarf. In summer months, I use it as a sarong to wear on the way to the pool. If we’re at Disneyland, it becomes a thing for us to sit on when waiting for fireworks or the parade to start. Very easy to hand wash, dries quickly.
- If weather warrants it, I’ll bring a sweatshirt and stash it in the Bento bag to wear on the plane if I get cold. Scarf/sarong also goes in the Bento bag to use on plane. Bento bag goes under the seat.
I also:
- get my suitcase & bag out about a week beforehand.
- lay out everything on the bed a few days before and I do a dry run with packing. This often results in 1 or 2 items being culled from the herd because I decide that I really do NOT need it…usually because I’m bringing too much stuff and I want to have room for souvenirs to bring home.
- When I first got started doing carry-on only luggage, I used a website called One Bag as a reference → https://www.onebag.com/
- instead of toothpaste, I bring tooth powder on trips. Does not have to go in the quart-sized liquids bag. Ecodent brand is available at Sprouts markets and works really well.
- Deodorant - I use a solid deodorant, not spray or liquid roll-on. As a result, it doesn’t have to go in the liquids bag.
- Body Glide - basically this is anti-chaffing stuff. Comes in a solid form. Prevents me from getting blisters when I put it on my feet before putting on shoes
- Liquids bag - primary items in here are shampoo & anti-frizz hair gel
- non-liquids toiletry bag - I put it out on my bathroom counter the night before trip. Pack everything in that which has to go w/me when we leave the next day. Otherwise, I WILL forget something.
- bring 1-2 extra pairs of undies beyond the reg. quantity that I’d planned to bring for the trip. Just in case.
- If traveling by air, I always print out boarding passes as a back up measure to our phones. And I write down on an actual piece of paper important travel info, like addresses of hotels, direct phone #s to the hotels, hotel reservation numbers, airline info, etc. That goes in a specific zipped compartment of my purse so it doesn’t disappear.
- Jewelry - I don’t bring extra. I wear a wedding ring and that’s it. The rest stays home.
Stuff that goes in the Bento bag:
- purse, wallet, cell phone, & related items
- liquids bag
- small electronics charger cord bag w/the 2 USB batteries
- if bringing a laptop, that goes in here, too
- sweatshirt & scarf/sarong
- if going to WDW, the UV umbrella goes in the Bento bag
- extra pair of shoes if I ran out of room in the Travelpro suitcase
- if a Disneyland or WDW trip, I always bring a USB-rechargeable fan
- non-liquid toiletries, including vitamins & meds + some travel essential OTC stuff like ibuprofen & Tylenol. Vitamins & meds: I portion these out in a pill organizer. If I was going to travel overseas, I’d probably bring the actually prescription bottles that showed the prescribing provider’s name and all that on it. But I haven’t traveled overseas in over 10 years, so I haven’t had to think about that type of travel in a long time.
- if trip is long enough to do laundry, I put some laundry sheets in here, too. Always in a ziplock bag. Throw out ziplock bag when empty.
- sun hat with 4" brim
- snack-sized ziplock bag containing some reg. band aids & blister band aids. Essential for a Disneyland or WDW trip.
- refillable insulated water bottle
- always wear the heaviest shoes on travel day
Am going to WDW for 5 days in late October w/my sister and I’m only doing carry on luggage. I fully expect to bring souvenirs home w/me, including a new sweatshirt so I’m not even going to PACK a sweatshirt at the start of the trip. If I get cold before I arrive, I’ll put on the scarf (I live in AZ, it’s not chilly in late October).
Meanwhile, the Spousal Unit packs like he’s on an excursion to Mount Everest. Brings a camping pillow (even when we’re staying in hotels), a huge camping towel (even though we never go camping), and twice as many clothes as necessary. So if the trip is for 5 days, he’ll bring 10 days’ worth of clothes. “Just in case.”
Are we traveling to outer Mongolia? No. We’re traveling within the US. 
He’s always over packed the entire time I’ve known him. LOL.
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I have never heard of a Bento bag. Sounds like a Mary Poppins bag!
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I have this also and Iove it so much! I have tons of skin care and hair care stuff - it used to be all over the sink. This keeps things nice and tidy both during packing and where we are staying.
On clothing - since researching packing for a trip to Italy in 2023 I’ve developed a capsule wardrobe with black as the foundation (pants, skirts, shorts, sweaters, shoes), with occasional pops of color in t-shirts.
It’s been great - really reduced decision-fatigue in traveling and in non-traveling life!
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My packing style is very similar and I have that same Travelpro 38L bag. My personal bag is a combo backpack tote. Always carryon if possible.
I’m a minimalist in all travel packing. I use something like this for a cosmetic bag.
And I use a smaller version for my TSA compliant liquid carryon bag.
I rely heavily on Ovcio featherlite cashmere scarves. They fold down into a tiny size but are amazing in keeping me warm, plus add a splash of color to my neutral outfits.
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It’s a little on the pricey side (but discounts are often available & they have sales often). This is my #1 favorite ‘personal item’ bag of all time. Bento Bag® - Personal Item Bag – Nomad Lane
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Very cool!
@Hello44 - I checked out the feathlight scarves - do they keep you warm in a cold plane? I’m always freezing and also use a scarf to attempt to block germs when sitting in a large crowd. Not sure if the uber light would work?
I don’t own enough clothes to do this! 
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I confess I don’t get the aversion to checking a bag-especially if you have correct credit card/airline status to get 1 free checked bag.
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Too many personal experiences with lost luggage made me a convert to only using carry ons.
Permanently lost or just delayed? I’ve had a few that didn’t make it on time (in decades of travel, it’s happened 4 or 5 times, mostly when a delayed initial flight just makes a now-tight connection) but never permanently lost anything. I pack a fresh top and undies in my carry-on in case it happens, but I still vastly prefer the convenience of checking my bag.
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I’ve had both situations. And one of the “just” delayed bags got to me after I was already back home and I had to replace everything anyway. And the reimbursement didn’t come close to covering the contents of the bag that was permanently lost.
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Ugh, sorry to hear that. I’ve never had a bag arrive longer than a day after I did. Insurance has been fine for anything we needed to buy during the delays but yeah if I lost an entire suitcase it probably wouldn’t be close to replacing the value of items in it.
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We mostly take direct flights, so it is low risk to check a bag (especially if we’ll be in that area for a while). And free if I am traveling with my husband, primary card holder for our Chase United credit card. Gate check is almost no risk for direct flights. Typically I travel with a backpack and a max-sized carryon rollerbag (which is easier for me to handle on the trip than a big bag), so I have options.
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Delayed or damaged checked bags sometimes do occur. It appears to be about 0.5% to 0.7% of passengers affected.
The risk is likely higher when you have connecting flights and/or flight delays/cancellations and/or rebooking due to flight delays/cancellations.
Some passengers are more willing to check baggage on the way home, because delayed bags at home are less of a hassle than delayed bags at your destination.
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Also, once I was on a flight where the incoming aircraft with greatly delayed. The airline offered to rebook passengers on another flight, but only if they had no checked baggage.
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