Delurked, she's not only a smart cookie, she sounds delightful, too, even if she might have been switched at birth.

My son won't buy new clothes at all. I thought it was just when he was in college and grad school, but now he has a real job, and continues to look a little shabby. He wears clothes discarded by his father and thrift store primarily.

I think I have read that the retail clothing industry is struggling because Millennials aren’t spending as much on clothing as we did at their age. In addition to paying down their student loans, they are spending their money on other things.

Donna, that's interesting. I thought Millenials had taken over as the drivers of the economy. Several years ago I was worried because it seemed like no one used a bathrobe anymore. I managed to find a suitable replacement, but as time goes on I think it will only get worse. In my opinion, if Millenials want or use something, it will be available, otherwise, maybe not. My son would say it's about time they take over from the Baby Boomers. He spends money on airline tickets.

Yep I think maybe my young adults don't spend as much on clothing as I did at the same age. My 21 year old son sounds like a younger version of your son Janet. Relative's cast-offs of all kinds. DD 2 has learned to follow me both with buying a lot of clothes and having trouble culling. It was so funny watching her and older sister last weekend. We have an old friend of Neil's staying this weekend for their high school reunion. So we were tidying the spare ( ex-DD 23's) room. She had a terrible floppy singlet she bought age 14 in Sydney, for $3, with a shiny coloured zebra on the front. She refused to let it go despite her sister being stern! It is 9 years old! I just watched, amused.

My faves, of the first group, are #2 and #4. I like the shape of #5 but the topstitching bothers me -- detracts from the sleekness your original pair shows. Also like the second Naturalizers and lisap's pick (though perhaps too-much-going-on if you want a simple+classic replacement). The white soles of the others strike me as more casual, not in the spirit of your originals, and not as versatile maybe? As always, though, depends COMPLETELY (or, say, 99%) on the comfort factor!

Jenni, my son wears things that I consider worn out, too. He still uses an 18 year old knapsack that I bought him in junior high. I offered him a nicer one we had here at our house, but he preferred the old one. I think he's proving a point, that he's not part of the retail economy.

Troff, yes, comfort will override everything else. So far, the first Naturalizers are wonderful. The Franco Sartos were delivered and they are a little loose in the heel, so they're out. Now I'm just waiting for the rest to be delivered.

I'm an older millennial and understand the resistance to consumerism. In my 20s my wardrobe was at least 75% thrifted or hand-me-down. That has shifted, I'm certainly down to less than 50% secondhand. Part of it is I'm more confident in my choices and don't mind investing in something if I know I'll keep it for a decade. I keep most things til they fall apart, or I sell/consign mistakes while still in excellent condition. I also have more income to play with than I did at 20. And much less free time; when I go to thrift stores now it's to shop for my child -- I don't like buying brand-new things that will be outgrown in a year (not having more kids, so no need to save hand me downs) -- so I'm left with not much time to browse for myself.

JAileen -- I like the navy Naturalizers! If they're the most comfortable, I think they fit your use-case perfectly. Have the Bass loafers arrived yet? I've tried the Weejun style about 3 times but they don't fit me well. Such a classic look, but I've finally given up.

This Millenial thread-within-a-thread is so interesting! I thought it was just my kid. When I was young I was poor and wanted to be rich. My daughter is rich and seems to want to be poor! She goes without things that I think she really needs, like a warm jacket.

Visually, I am most attracted to #4 in your first row, and #1 in your second row. And #5 in the first row is nice and classic (but the others I have listed look more exciting). But really, let comfort be your first priority. Always important for walking shoes, and especially with a toe like yours.

I like kkard's suggestion, too.

LaP, thank you. I'm glad you like the Naturalizers. The other two pairs of Naturalizers are likely comfy too. It's interesting about consumerism. When I was working I had a very small wardrobe. I tried not to wear the same thing twice in the same week. But I wore them over and over and over. Why didn't I have more clothes? I'm not sure, but I didn't feel deprived.

Laura, I'm glad to hear about your daughter. Last year our son moved to Minnesota. For his birthday we gave him money to buy a down parka. Did he buy one? No. He wore a down jacket I made in the 70s (anyone remember Frostline kits?). He was lucky, although it did get below 0F, the winter wasn't as bad as it is normally. I was pretty horrified, though, when he sent a picture of him with frost on his beard!

Cat, thank you for offering your thoughts. The Franco Sartos are out (loose heels), and KKards's Tretorns are sold out. I did eventually order the navy Adidas from Nordstrom Rack, though. So that puts me at ten pairs. Yikes!

Update: I've kept these Naturalizers, Adidas sneakers from the Rack, and Vionic flipflops. I've already worn the Naturalizers and the Adidas. All of the other shoes had fit issues, mostly loose heels. When I returned the shoes, to Macy's and the Rack, the SAs were very nice when I told them about my broken toe.

Yay! Those Naturalizers were my third fave after the Calvin Kleins and Franco Sartos. And I like the Adidas. And Vionic flip-flops too! You will be joining the owning 50+ pairs of shoes brigade any moment! And can you believe after ditching 3 pairs of high heels, I am no longer in it? I'm in the 40-plus pairs group now

Looks like good choices. I’ve recently tried on some flats - I prefer with just a hint of heel, and of course must be comfortable too. I have a hard time keeping most of them on my foot. Adding to my finds. I like ordering from Macy’s, plus lots of colors available in case they work. I’ve tried Vionic on, and think I’d enjoy the arch support, but those never stay on my feet. Those and fit flops seem especially wide in flip flops.

Great! I'm glad these three worked out for you. Navy flat shoe capsule is ready to go!

Jenni, I'm glad you like them. I really need to count my shoes.

Delurked, the flip flops are a little wide, but feel pretty good. The Naturalizers are surprisingly comfy, and look nice, too.

Firecracker, thanks. It felt good to return the shoes that didn't work out.

Those Naturalizers are gorgeous! Glad to hear the outcome.

SOOOOO fab on you. Love what you chose.

Robin, thank you.

Angie, I'm glad you approve.

Good choice. I need to thank you for introducing me to the brand. I've rarely seen so many comfortable shoes that look as good as those. I'm now slightly obsessed with their work clogs.

Approprio, those look very nice. I hope they work for you.

I just stumbled across this post and enjoyed reading it. I've heard you mention your Naturalizer loafers a few times, and now I know what they are! I would've voted for them and maybe the penny loafers, because Bass and Naturalizer are brands I've trusted for a long time and because they will outlast the trendier platform and pointy-toe options, style-wise. Had to laugh at all the numbers comments--the 50+ club, "oh no, I'm up to 9" and the daughter who would only buy one pair. I get frustrated with my son like insisting he only needs 1 when things are on sale, then wanting another a week or 2 later. Counting the 3 in storage in the US, I currently own 16 pairs of footwear. I might get winter shoes that have some pink on them, and maybe something more formal for summer, but I don't see expanding much more, as much as I like looking at shoes (they are a large part of my finds).

FashIntern, teenagers can be so annoying. My son is well out of his teens (actually he’s out of 20s!) and he is still annoying at times. Now he annoys me just for fun.

So does mine, lol--he's only 16, but has all those buttons figured out.
Last night I told him I shouldn't listen to some of his music any more, because I nearly addressed him with a word I don't want to use. (I don't want him to use it either, but that's his business) His response? A clip from The Boondocks featuring exactly that word. Turkey!

Old thread but I havd the navy Bass penny loafers. The fit works for me and the pebbled leather is very forgiving. But not as much a shoe for dresses for me— mostly pants- although I have these in blush that I manage with some skirts.

Unfrumped, I thought the Bass penny loafers were excellent quality, but the heels were too wide for me, and they slipped off when I walked. It’s hard to find a shoe that is a good fit, good quality and attractive design, at a reasonable price. It’s the holy grail, isn’t it?

Great choices JAileen ... might copy you on the Adidas!