Yes Diana! Totally agree.

I think the footwear issue for me is that as I've gotten older my feet have just gotten a lot more fussy. I need more support and yet my feet are higher volume and a tad on the wide side, so inserts just do not work, at all! I am starting to understand why my mom gravitated towards shoes-with-laces around my age, and never went back. Not saying I'm ready to give up just yet...

Shoes in my closet that work well right now for walking:

1. Munro booties. Have a bit of a heel, but not too much. My feet start to get cranky however if I'm walking all day long. They are also heavier than sneaks so my legs just get tired after awhile.
2. Black Naot sneakers without laces. I can walk forever in these. Lots of spring and give and ample arch support. They are sneakers technically but look a bit more fashionable. I'd like to add more in this category, I think.
3. I have some metallic Clark sneakers that look adorable but alas they do not offer enough arch support. I actually find the Munro booties with a bit of heel more comfortable for walking. I guess my feet don't like really flat shoes. Same goes for ballet flats -- the SW flats are uber-comfy but no arch support.
4. Flat tall black boots (forget the brand). They have a smidgen of heel, not much.
5. And of course... Asics sneakers... but I only wear them if I am wearing exercise clothes.

I don't want to live in exercise clothes -- if I did that, I'd look totally out of place next to my hubby, as he will be in jeans, a dress shirt, a nice sweater, and boat shoes. I have no idea how he can live in boat shoes -- no arch support at all!

I love the Boston area! I attended college in Boston and lived in the Back Bay area for several years. It's a great city, especially at this time of year.

Interesting to hear how much you are finding the style sensibility of your neighborhood is differing from your old place. I run into that almost every other week with how much I travel! At first I tried more to fit in wherever we were, but over time I've decided that it's just impossible. For instance, last month when we were staying at a seaside location, it was extremely casual. A lot of the younger local women wore their pajamas to run errands. I don't think I would ever do that unless someone had stolen every other conceivable article of clothing I owned, so I just decided to dress how I wanted when we were out sightseeing or shopping. I am often the most dressy person I see all day in some of the small towns we visit. And it's not like I'm dripping with diamonds and pearls!

You mentioned your goal is to walk to the downtown area, so you'll be spending time downtown on your walks, and not merely in your home neighborhood, so you'll want to fit in there as well. Those skirted leggings are very 'city' to me, so they sound like they'd be good for both locations.

I like the shiny puffer coat sensibility, but I also love the wool/cashmere coat sensibility too. To my mind the rest of the outfit is more important than the coat as to what vibe it has. Lots of people who dress quite casually actually are wearing an outfit where the puffer coat is the dressiest piece. Another way I've seen people wear it is to let the puffer coat be the way to make a smart outfit more casual.

I agree with shoes on up. Or at least, start thinking about categories of walk-worthy footwear and see where that takes you.
For me it would be:
Some types of slip-on sneakers, but sometimes they "slip" too much !
Some oxfords if cushy, and maybe rubber rather than stacked leather soles, as wear out on pavement
Flat boots, also need roomy toe box--pointy toes out, tapered can be iffy. So to have stylish roomy toes would try to amp up style in other parts of the boot.
Some types of lace-up sneakers if they are streamlined shape and style and the whole outfit could be elevated. And leather sneakers. I may be in the weeds, but I think the sneaks pass muster even more with rolled jeans, ankle pants or ankle leggings.
Some types of "European comfort walking shoe". For me it might be dark tonal look to be very distinct from a white trainer, for example.

Anyway, some of these styles just work better with dresses, vs, BF jeans, vs. leggings, and so on. And color can make a difference.

Reading your reply, Ginger, for some reason it clicked with me. I don't think my new neighbors look sloppy at all. I think they all look urban fashionable -- just casual.

Maybe it's because they are all way more fit than I am, with all the yoga and walking to the Whole Foods and post office and all that every day!

Casual / Sporty Luxe definitely looks better if you are fit and trim! I hit menopause with a skid and a bang this past year and I'm kind of fleshy these days. Though I am feeling muscles I forgot I had, since moving here.

Unfrumped, totally not in the weeds. I see those details too, though rolled/ankle looks just aren't practical in our colder weather months.

Your feet sound like mine (high volume, etc) and I just discovered the brand Atelje. I have an extremely high instep and there was room to replace the insole in these sneaker-boots with my very thick orthotic. Since that worked, I bet the existing insole + something like superfeet inserts would also work.

I love the looks Angie posted with the luxe sweaters and leggings.

Hi Shiny --

Congrats on the move, sounds amazing overall.

Two quick things to add to all the great advice above:

1) To me your style has no shortage of feminine, sleek, and/or dramatic elements (I notice as I often look to steal inspiration from you given my love of same).

I think this is why I struggle so much with sporty/casual, even though I need it because I do walk/errand run a lot. I've done a lot better since I've tried to limit my purchases to ones that have one or more of the above. The outfits you listed seem right in line with where you should be, so I'd just keep an eye out for (feminine, sleek, and/or high-drama) performance wear that you can combine with your "regular" washable clothes.

2) Check out retailers who fit for/sell the "Superfeet" line of rigid arch supports. I've added them to my life and noticed it helping many things. I'm pretty much a comfort shoe junkie but my arches are super-high and even the comfort lines don't always cut it, grrrr. Adding these to sneakers, boots, booties etc = improvement.

shiny, I think you will get there fine with various types of "juxtaposition".
Sort of what Ginger tea said.
For example, the red AT coat might in another context be worn with luxurious camel woolens and cashmere, gold jewelry or pearl statements, or strict architectural black and white, and so on for business wear or very smart casual.
But for neighborhood walking, leggings with Breton striped tunic and some sporty sneakers, or Greyscale's great high-tops, and maybe a scarf that has a distinctly casual or playful vibe--things that make use of the vibrancy of the red, and the fact that the fit and shape are great, but not as much the luxury nature, if that makes sense. Making outfits more "approachable".

I live in Charlestown! I'm currently one of the stay-at-home moms you've seen at the grocery store but spent the last seven years as a working/commuting mom hopping on the 92 bus. I agree it's more casual than most city neighborhoods, but I'm surprised you felt out of place in a red coat. Another factor is that Charlestown is far more economically diverse than Newton, so obviously expensive accessories and clothes feel out of place in the day time. In the mornings and evenings, the commuters are home and the fashion is more business-y/expensive. I highly recommend focusing on your shoes first. I have Joseph Seibel leather lace up sneakers that work well for neighborhood walking, and Chelsea boots or SE Petty booties work well too. The looks Angie suggested were on point if you shorten up the sweater length. If you don't like jeans, skirted leggings and ponte pants are good. Check out the Converse concept store that's just over the bridge to see if you can find some fun sneakers, too. To really fit in, you'll need a Bruins jersey :).

Robin! Let's go shopping, neighbor!!

No wisdom, just wanted to say that this is such an interesting thread!!!

I grew up in your neck of the woods and just returned to Wellesley for a reunion a few years ago. I had forgotten how cold Thanksgiving weekend could be! Definitely needed the down jacket to do Lexington with my daughters. We've been fantasizing about moving to Minnesota (crazy, I know, but our daughter has lived a few hours from St. Paul for the past few years and it doesn't look like she's moving back east anytime soon) and St. Paul's Grand Avenue feels the most like "home" to me, style-wise. People are infinitely nicer in the Midwest than Massachusetts, but the level of dressiness in St. Paul seems just about like Newton-Wellesley. Lots of black, black down vests, black leggings with black quilted skirts, black boots, but pops of fun color in scarves, boot socks, gloves, hats.

I'm loving the sound of Charlestown and your new life, Jennifer, congrats! And I too have been following along with interest. I totally understand the need for comfortable and stylish shoes that (literally) can go the distance because I walk everywhere in Antwerp too. The only difference is that you see all levels of casual and dressy here:-)

Starting with footwear sounds like a smart plan. Fun sneakers are one option, as are booties, ankle boots, tall boots, oxfords, sandals, slipper flats, "snow" boots... as long as they give you enough support for walking longer distances. My feet are on the high volume side, and I'm currently completely in love with AGL. Their shoes are soft, extremely comfortable, interesting, and there's a nice assortiment of styles (casual and dressy -- I like the juxtaposition of a dressier shoe with casual or Sporty Luxe looks, but casual from head to toe is just as fab -- to choose from).

I could e.g. see these work for you and your new style:
(I have these and they are a-ma-zing)

And for next Spring

Adding more sweater dresses to your wardrobe also sounds like a good idea, as do ponte knit pants and athleisure wear. Maybe tube pencil skirts in a knit material for Spring/Summer? And how about some knit jackets or blazers for ease of movement? Ooh, what do you think of a fab cape or poncho as a topper to throw on over everything from a dress with leggings, blazer with jeans, Sporty Luxe looks to more dressy outfits for work and leisure?

Other casual pants with a nice amount of stretch might work too. Something like the KUT plaid skinny stretch pants perhaps.

I also love the ease and comfort of their 'Diana' stretch corduroy skinnies, plus they are available in such fun colours.

And I know you don't like jeans for walking, but I would like to suggest the NYDJ's 'Clarissa' skinny ankle jeans anyway. I have them in the light blue, they are extremely comfortable (you can't even tell they are "jeans"), stretchy and not constrictive in the tummy area at all (I walked all over Amsterdam and London with them this year).

All three styles of pants work well with sweaters with asymmetrical hemline like the Halogen tunic sweaters (finding some in machine washable fabrics won't be too hard), and they are also fun with (shorter) poncho style pullovers layered over a crewneck or turtleneck T-shirt top.

I hope we'll get to see many photos of you showing us your evolving style!

P.S. How about adding one or a few more upscale backpacks too (sounds like the one you have now is getting an excellent workout;-) I love the Matt & Nat brand for those:

I just found this in my inbox, and I am intrigued: Dress Pant Yoga Pants. Could be an interesting option for you too, Jennifer?

They come in four different styles, various colours (even some subtle patterns, which I love) and are apparently very comfortable. They are getting great reviews:

Shiney you look like you like you skin. That's what's so cool about being a woman.

Inge - you are excelling yourself!