This is a HEWI for me and has been for awhile. I may be over-thinking it, or my requirements are just too high and unreasonable, and I need to compromise somewhere.

Requirements:

• I WFH and travel 50%, so I only need this bag for the travel part
• Needs to fit a 13 inch Mac Air, but more than that: a scarf/sweater for the day, comb, wallet, lipstick etc etc.. everything I need for the day
• Can't overwhelm my 5'0 frame
• Prefer long straps, to carry on my shoulder, rather than on my arm
• Would like it to be lightweight yet
• Real leather .. (this may be where I need to compromise)
• Either has to be able to fit within a carry on bag OR has a way of strapping on to my carry on bag handle, and then it's probably got to be a little larger to accommodate some more stuff.

What I've been doing while waiting for the HEWI
I started by using a fairly large, nylon bag that slips over the handles of my carry on. It's super lightweight (a plus!) and can pack a lot of overflow stuff for longer trips. I would tuck a clutch inside as my day purse. But when I'd empty it out at arrival and pack it with just what I needed for the day, it is clearly TOO BIG and looks wrong with my 5'0 frame.

Next I tried just carrying a clutch with laptop in a simple sleeve. That works okay but is annoying when going on from business meeting straight to social hour/dinner. And also, no room for a scarf/topper (it gets cold in those conference rooms!

Next my mom was decluttering and from her I got an inexpensive pleather bag which is not intended to be a laptop bag but is the PERFECT SIZE. And weight. And (empty) it slips right into the outer pocket of my luggage. It has convenient pockets on the outside for hotel key & cell phone. Zippered middle pocket. And a fun patterned lining. And just barely enough room for a scarf/topper. Only drawback was I'd have to shuffle wallet and other purse items once landing, and before getting on the plane again.

Unfortunately, since it's pleather, and I've been cramming it in the outer pocket of my luggage, it's showing a lot of wear and needs to be replaced. For reference the size of this nearly-HEWI bag is 11x16.

Bags I'm considering

Lo & Sons 13" Seville -- I like that it comes with a sleeve that slips on over your luggage, and has the option to swap out the shell. Except the shell has to pack in your luggage, and I'm not sure I want to take up valuable luggage space. Also at 12.5x18 I worry it may be a tad too large for me (and maybe most of that extra inches is taken up by the design, rather than being usable space?) It's also 2.6 lbs!!

Haerfest Eva tote -- 11x14. Looks like a beautiful bag. I like the strap design. Not sure what it weighs. And no zipper.

Cuyana Work Satchel -- 11.5x13.5; weighs in heavy at 3 lbs. Not sure if I like the straps. I'd prefer a shoulder bag to a crossbody. I don't think I want to carry my laptop in the crook of my arm.

Daame Dana Tote -- 12x13 and the lightest at 1.4 lbs. Don't know anything about this brand.

Knomo Audrey -- my sister highly recommends.

What have I not considered? Suggestions? Advice? Insights?