Greyscale - shoulds were my bane for a long time. I would get sucked into the perfect white shirt, denim button down, pencil skirt and I never wore them. I ignore shoulds now and try not to get tempted by others that rock them so amazingly. OTOH, when I broke my toe 2 yrs ago and developed seural neuritis this year I've been wearing my gentle soul bay uniques. I love boots/booties, I typically hate shoes esp flats, but these called to my inner ballerina and they are insanely comfortable. At the time, all I could wear were merrel mocs and the gs. the merrel mocs have gone but these little flats, well I've come to adore them. Some things we love at first and somethings we come to love at last. That being said, I would not buy something that did not speak to me unless I was desperate (the merrel mocs leather - love the breeze but not for work). Excruciating foot pain trumps style any day. That being said, born crown makes a fabulously comfortable shoe/boot. Would you consider something like this...http://www.zappos.com/born-kam.....full-grain Looks like the comfort version of the JC everly but if the soul is similiar to the other pair they might be very comfy. Just thought I'd mention. But bottom line is if you can't walk without pain you will be miserable and not enjoy your trip. Happy feet above all!!

I understand the "shoulds" and I've gotten a lot better at anticipating what is actually going to get used in my wardrobe vs. ticking off a box of "what most women should have in their closet."

But on to travel wardrobes, specifically shoes. I'm with Anna. My travel choices always err on the side of practicality, unless I am factoring in some romantic or special occasion with hubs (i.e., when we went to Europe and were planning on a splurgey date night in Paris).

I bought these Sketchers (from my Finds) right before I went to Cuba because I wanted a spare pair of closed-toe shoes that could withstand full days of walking in a hot, rugged, climate that would include city walking, as well as the possibility of some more rural "hiking." Boy, am I glad I did. I had taken my snake print slip-on sneakers, which are typically really comfortable, but I neglected to factor in the fact that it was March, and I had not worn that kind of shoe without socks in months, so I had my tender winter feet still on. The first day in Miami, before even boarding the flight for Havana, I had blisters. I ended up wearing the Sketchers every day for the following 10 days (along with some moleskin!). I also had a pair of flat sandals with me that looked OK with the occasional jersey dress I wore out for dinner.

Are those Sketchers the most fab thing ever? No. But they work with my decidedly gear-ish casual travel wardrobe and kept my feet comfortable so that I could enjoy tons of walking and photographing without giving my feet a second thought. So if you find the holy grail of comfort for a travel shoe and it's good enough, I wouldn't worry about it being the ultimate in fashion.

On the matter of shoes, I'll join the chorus for comfy. If the shoe is comfortable, you will be comfortable and confident, and how you feel in your shoes affects how you will project every other aspect of your style. I think you could make those shoes work in every way if you are confident wearing them. If you have serious doubts about how you look in them, though, maybe you should pass on them. But only for that reason. I think they could be winners.

As for shoulds... I've had to accept that while blazers are shoulds for the many, I am one of the few. I don't feel myself in them. I used to wear blazers all the time when I was working (because "should"), and so I know how to wear them and even for a while had quite a collection of designer blazers that were lovely. But rather than me wearing them, they were wearing me. I'd take them off at every opportunity and felt much more like myself. So now that I don't have to wear them, I am a much happier person.

Another should that has never really worked for me is... the ubiquitous white shirt. I love the look, just not on me. It's not the white, it's the style of the shirt. Something about that style and my breasts, or shoulders, or, well, it just doesn't look good. If I can't wear a buttoned shirt open over a tank or something else, I can't pull it off.

Chiming back in here since this is an issue near and dear to my heart.

On a vacation like the ones that Janet describes -- well, the answer is obvious. You find something like the Sketchers and go with it. (Those look like great summer sneakers, Janet, and so glad they saved your feet and your trip!)

The real trouble comes when a person is trying to do what you are trying to do (and what I am usually also trying to do) -- combine a more work-or-dressy look with footwear that can also go the distance.

It's a whole heck of a lot easier for both of us in temperate/cool weather. Boots and booties all the way! Those work for comfort (usually) and they also work just fine with our (quite different but equally slightly androgynous and modern) styles. Problem solved.

It's the mixed warmer temps that provide the difficulty. Times when you might want to wear a skirt or dress or shorts as well as full length pants.

I'm still in favour of buying any shoe that is "insanely" comfortable and considering it a travel investment. Unless another equally comfy and versatile shoe comes along, go for it and put it away when you aren't travelling. That is basically what I have done with my old Ecco Mary Janes -- and believe me, they have earned their CPW and then some.

Totally hear you. For me it's crisp white shirts.

Fwiw, those shoes seem to me like they might work with your style. Heck, if they are comfy....

My two cents:
If these shoes were just comfortable with a small c, I'd likely say hold off until you find something more suited to your aesthetic preferences. But these particular ones sound like they're well above that average comfort bar and uniquely suited to your specific footwear challenges. Considering that you've found something elusive at what I would consider to be quite a reasonable pricepoint, I wouldn't hesitate to keep them and lean heavily on them during times when comfort is paramount. Because I couldn't agree more with Anna - fashion should complement your experiences, not dictate them.

As to the classic should haves...I'm another one who struggles with the white shirt to a degree, but more for fit reasons than because they don't suit my style. I flat out refuse to purchase a tan trench coat, as I think it sounds like the most deadly dull incarnation possible. Any other shade and I'll try them on all day, but tan is simply not happening. I'm far, far happier in my bright blue trench purchased this spring than I ever could be in even the most impeccably-made garment in such a lifeless shade. My third contrarian position has to do with...bootcut jeans. For years I subscribed to the notion that they were universally flattering, but these days nothing makes me feel less fab than this old standby. I bought a pair during my fall style refresher. While every other item I purchased that day saw regular service for months, the bootcuts got worn exactly once. I think I'm done with that silhouette.

I'm in the comfort camp - these shoes sound so comfortable for your unique foot shape that I would buy them for your sight-seeing niche.

I used to buy the "shoulds," but they didn't get worn. Now I buy for my present lifestyle and needs. This month, the focus has been on finding shoes for my fussy feet - pain from osteoarthritis. I don't particularly care what people think I should wear.

I vote to keep the comfy shoes - regardless of style.. When you travel, happy feet are key. Style is a distinct third.

On the topic of "should," I've bought office clothes, including a blazer, that never get worn since I dont' work in an office. It's a maddening habit of mine that I'm trying to break.

The only thing I can suggest is to not spend too much money on something you only sort-of like, even if it's useful to you.

I find it very hard to buy 'should' items, and often will be inappropriately dressed because of it.

I can't seem to bring myself to buy a sensible walking shoe. I have a hard time buying 'event' clothing (think dress pants, dress shirts, suiting, and day dresses). These things involve crisp lines and (typically) polyester/nylon which I don't like.

Just to add, I was chiming in on the "should" issue rather than the travel issue. :). My travel shoes are a pair of Jambu Mary Janes. They are comfortable to walk for days, and I've hiked in them and worn them to dinner. When I travel I bring as few shoes as possible unless it's a dress-up eventfest like a film festival or wedding. Otherwise I'm all about function.

One the topic of travel shoes: as a person that now must negotiate orthotics, I have come to the realization that style and function will never-ever-ever meet 100%. You can get one or the other 100% and then hope that the other will be somewhat close. Actually, this is pretty much my whole shoe-life now whether I am travelling or not. So I have decided that I would rather have a comfortable experience than to miss the experience/suffer. Its just shoes. (sorry, did I say that out loud????)

On the topic of "must haves"...well I think there is some wisdom to these lists. However, I use them as a guide. For example, on the beige trench. I have chosen a black version with a moto-style opening. So fills the FUNCTION but the style is more Marlene. I like blazers...but not traditional corporate styles. I choose versions that suit my style better than the classic/conservative style that is shown in the lists. But I have discovered that when I have my version of the items on the "must have" lists, my wardrobe functions better.

Slight update - my orthotics don't fit perfectly. Possibly close enough, once the vamp stretches a bit. They're still very comfortable with the insoles they came with, which are more padded and perhaps nicer for long walks.

I only wear my orthotics a few days a week. They're more for long-term foot health than fixing any immediate pain, now that the injury healed. But it would be nice to own a few more shoes that can accommodate them.

To answer your question about certain "must haves" that I don't have:

A pencil skirt doesn't suit my body type

A suit doesn't fit my lifestyle, so I don't own one. I do have blazers, but they aren't "suit" blazers.

A white button-down shirt doesn't flatter my personal coloring, so my "white" button-down shirt is cream.

Because of pain from osteoarthritis, I can't wear pumps or pointy-toed shoes or heels over 1.5 inches. There are other shoe types I can't wear, but these are the real killers, and they seem to be on every "must have" list I see.

I tortured myself with ballet flats for years before it finally was brought home to me that they are just a bad idea. I've only ever worn flats and ballet flats seemed like the perfect option for summer, but they just won't stay on my feet.

I would have a hard time turning down an insanely comfy shoe that's not gear. . . .But do those have sufficient arch support?

As to *should owns*: I once had a LBD that I never wore. My dressier black pants and white shirts don't see much action, and I don't wear them together because I don't want to take anyone's order. I never wore my denim jacket until I performed surgery on it, and now I wear it as a vest quite a lot. A few years back, I bought two pairs of black pumps, patent and regular leather. I have a tough time keeping them on my feet and only wear the patent ones. I will probably keep the other pair until they go severely out of style and/or I retire, whichever comes first.

Oops!

I'm glad I don't work in an office where I'm expected to wear suits, pumps, etc. I used to wear that stuff, but didn't like it, and I always wore athletic shoes to walk from my car to the bldg. Now I can wear pretty much anything that's not strictly casual. There are people (including my boss) who wear strictly casual clothing to work because of the nature of the work they do. I don't do that, though, because I want to present a more professional image. I also don't like dressing down like that. It's just not my style. I like adding dressy touches to my outfits without going OTT for the occasion.

I like AG's analogy. The shoes are Doc Martens little cousins. How adorable. If I could find shoes that looked close to my style and were comfortable to walk in I would buy them. Okay that would be Trippen.

I am not sure if I ever bought should items. I did buy a white button down shirt that was impossible to wear. Also not my style. So I guess I did. Never again.

I bought a pair of Sketchers like Janet's. My DIL buys this brand and loves them. They are incredibly comfy--for about two hours on my feet. I wore them one morning to the grocery store to get a few things and by the time I got home--ouch. These are not shoes for those of us prone to plantar fasciitis. Even though I have tender feet, I need a hard soled and well-cushioned footbed. So sad--maybe I can wear them around the house later when I get my feet back in shape.

I've never had a trench coat I've loved. I kept trying to find one, but most belted coats/jackets are belted too high for my long torso. Also, now I have the Apple Belly thing--and it doesn't come from Steve Jobs.

I have a hard time wearing white, and I hate to iron. Off white yes, but that white shirt/blouse is something that is harder and harder to wear.

I don't wear dresses much, so I'd prefer one in a pretty color. Way back when I was fairly newly-wed, the wife of the leader of our church group invited all the young marrieds to an evening at her fabulous home in the Hollywood Hills. Of 25 or so of us, more than 15 were wearing LBDs, and I did count but can't remember exactly. Maybe it was 20. That kind of turned me off to the concept. Yes, I was there in my LBD that I had carefully sewed from a Vogue pattern.

Our lives have changed a lot since those early days when the first must-have lists came out. Maybe if you live in a big city you need the items. My must have list today is much different.