Nice to see love for Sketchers. They're my favorite brand recently, my last two pairs of shoes have been Sketchers. Something about their designs fit my feet better than other brands. I've had their working shoes and now their relaxed fit. I don't care about labels, I just go with what's comfortable and looks good.

Carry-on only traveler.

I only bring the shoes I am wearing.

Skechers
 

They also seem to fit my feet very well.

I'll clarify that the Skechers OTG Lux pair is specifically for packing, because of being so light. I prefer a sturdier shoe for serious walking, and change to the Skechers for the evening. The Lux design has a black sole, so it's sufficiently sub-fusc to wear to a concert or play. I'm too old and/or too staid to wear a shoe with a white or neon sole for such occasions.

For what?

For weekly business travel, if leaving Monday morning, I wear dress shoes and pack gym/running shoes. If I leave Sunday night, I wear the gym shoes and pack running shoes.

For vacation - same, but gym shoes vs. casual shoes, plus water shoes if it's beach trip, or boots if it's a ski/snowmobile/etc trip.

Clark's "Active Air" pair of Mary Janes. Absolutely excellent quality and last forever, and/or pair of Merrell's slip on things that also last forever and well made. They both slip on and off easily and are very comfortable.

suede has not-so-slowly assimilated my wardrobe and pretty soon will push out all of the calfskin. casual suede bluchers. suede ankle boots. suede oxfords. suede loafers. so there'll be atleast 1 pair in luggage and/or on my feet

The problem I have is that depending on the trip, I need some combination.

Dress
Smart Casual
Casual
Running
Tennis
Golf
Sandal
Ski Boots
Hiking boots

At most I carry three (wear one, two in the rollerboard), but most times I really need at least four pair. I've partially solved the problem by spotting shoes at different locales around the planet, but I'm still looking for a shoe that will double for dress and smart casual. I've tried nice mocassin style shoes (e.g. Bally, Magli) but have never found the right color style combination to handle both dress and smart casual. Have to believe there's something out there that crosses the style divide.

I'm also always looking a compact athletic shoe that's good for running, tennis and golf. Usually I pack a pair Nike free which don;t take up much space and can be used for tennis and golf in a pinch, but I'd really like to find a tennis shoe with a collapsible upper.

I have some closed toed Kane sandals which are pretty versatile. Wear them on the beach and for casual in cooler weather with a pair of socks.

What I need when I get there, not counting what I am wearing on the plane. What I am wearing on the plane is almost always whatever pair of sneakers I own currently.

Given that you've listed off more possible types of shoes than I own (currently 6 pairs, two of which are an older and newer pair of the same Tevas that I try to rotate), I can't relate much.

In terms of how to pack them, if I have to pack non-sandals (e.g. if I going someplace cold and wet -- for casual hard shoes -- or going to a formal dinner), packing something in the shoes is a good way to avoid space being wasted -- usually socks, although if I ever flew with the work boots I use for motorcycling I don't think I'd have enough socks to fill them (I haven't, yet, and might just wear them when flying to avoid the hassle of packing something so bulky.)

Good luck with that.
1) Not reasonable to expect a general question to exclude half the audience, even if you're only interested in one half's responses. Then again, perhaps you've put them all off by referring to them as "chics."
2) A few folks never check bags, a few folks always do, but most folks sometimes do, sometimes don't. See #1, even if it's not necessarily half the audience.

You sure you're not a "chic"? :D

I suspect flyertalk is not the place to answer whether there's something that "crosses the style divide."

I am a fan of Rockport Dressports, as they are comfortable enough to wear anyplace sneakers won't do but at the same time look dress-shoe-ish enough for someone like me to wear anywhere I've had to go (including the twice in my life I've had to put on a tux, and the twice or so a year I have to dig out my suit.) My pair is about 12 1/2 years old (and still usable, although there are a few very fine cracks in the leather, and I wear them probably a half dozen times in a year), but pretty much these... doesn't look like they've changed much.

apron bluchers
suede monkstraps
chelseas


take your pick

For the London trip, I need to understand you slang. What is the difference in "running shoes" and "sneakers?" Do you wear running shoes as casual footwear, or only for exercising?

For the 8-day Dallas trip, was that mostly for business? Only one pair of dress shoes for multiple days of work?

They're only "chics" when it comes to buying shoes and movie preferences, the rest of the time they're women. ;)

For London, I use running shoes to describe exactly that. I'm a marathoner and so I have two pairs of shoes I use for nothing but running. They don't look great and are filthy from trails so I could never wear them out. The "sneakers" I brought were for wearing to the office and at the weekend (link to the exact pair I brought).

Dallas was 5 days of business, 3 days of weekend and time working in the hotel. Never saw a need to bring multiple pairs of dress shoes if one pair goes with both suits.

I always pack some walking shoes like nike frees and some dress shoes like loafers or wing tips.

For travel, I'm a big fan of a couple of the ECCO styles. They're sturdy enough that I can hike trails in them, but after a quick dust off they'll just pass for decent evening shoes unless going to a very formal event.

However, unless I'm on a very short trip I always pack a spare pair. I've learned the hard way that sometimes even a pair of your most comfortable broken in shoes can "turn on you". Good to have a backup.

I've got two pairs of Eccos and use them as my main shoes when traveling for business. They work fine with business-casual clothing and are just dressy enough to wear with a jacket and tie. They're comfortable enough for walking around town all the day though I wouldn't wear them trail hiking.