I find casual hard also, but for reasons a little different. It is mainly because when in the company of other friends doing fairly casual stuff e.g. when we go out for a beer at the Irish pub down the street etc., I have to deal with them feeling under dressed. I guess it just boils down to the fact that I put just a teensy bit more though into what I'm wearing, and maybe spend 2-3 mins extra getting dressed

I relate to most everything that has been said already. Except I don't know if anyone said this yet: I just feel totally frumpy in most casual wear, the "jean-gap tee-sneaker or other sturdy flat shoe" look. I don't mind the jeans so much anymore (once I found my citizens!), but it's the rest of the casual uniform I don't like. Yes I have Cons, but I still feel horribly clunky and frumpy in them whenever I wear them.

I also dread the summer months and my aging body needs structure and layers! I do not like to bare my shoulders in tank tops and spaghetti straps and most floaty breezy dresses look awful on me.

I am so extreme on this, I doubt I'd ever move to a southern climate because then I'd feel under-dressed and frumpy most of the year. One of the reasons I like my urban area is because it gives me a perfect excuse to take it up a notch and go smart casual nearly all the time. I would much rather be a bit over-dressed, than feel frumpy.

And don't get me started on the years when my kids were breastfeeding and frequenting playgrounds! Ugh. I cringe when I look at the old pictures.

Last summer was the first summer I've ever felt "just right." Not every day with every outfit, but getting there. Thank goodness for denim clamdiggers, sweet pea tops, and Me-Too ballet flats!!! I just bought yet-another sweet pea top yesterday, in fact, thinking forward towards the summer.... yes I know I'm supposed to be on a shopping ban but the pattern and color - I couldn't resist.

Hannah - I've been thinking that you might really like the Me-Too Lacie's I have. They are so incredibly comfy (12-hour shoes! I can walk all over town in these, no problem!), and this style is a bit more sporty/less dressy. I would get them in the bronze so they don't show dirt. I am going to live in these all summer...

Otherwise, I've been lately noticing Puma's on everyone's feet around here. Not with clams but with long jeans. I would like to give those a try, as an alternative to Cons. They look more streamlined to me? Anyone have Puma's?

Patience, I love the description of your strawberry-picking outfit! Wow, I bet you were the most stylish person on the farm! I am looking for something much much lower maintenance: no white, and actually no jeans either because of the weather (way too hot for denim).

Shana and Shiny - yes! as I grow older (and unfortunately heavier than I used to be), I must have some structure in my outfits (Christine, you mentioned structure too, so I know this is not only an age issue). Otherwise, I feel frumpy, clunky, dumpy, and the whole load of unflattering adjectives. Shiny, I did love living in Boston for dressing up and for the fact that there are not too many hot days there Alas, I was pregnant for 9 months out of 2 years we lived there, so this was a fashion challenge in itself. Playgrounds are quite a fashion challenge, aren't they? Shiny, in the terms of shoes, in winter I manage with my city sneakers and mary-jane keens. In the between weather, I have comfy ballet flats (not the apple green ones - I have a black pair from a while ago that looks like ballet dancing shoes and is very comfortable). But, it is way too hot now for closed shoes, so I don't know what to put on my feet. I don't want to resort to athletic sandals, but I guess a sandal that allows you to climb the playground equipment has to be gear? Or not? BTW, I don't have Cons exactly for the reasons Shiny mentioned - I feel awfully clunky and frumpy in them.

Shiny, how well do the Sweet Pea tops hold up in frequent laundering? I saw quite a few on e-bay, and if they can be washed and brutally tossed in the dryer, I might be tempted ... Do they make sleeveless tops as well?

I think this is a missed retail opportunity: YLF-approved "play clothes" for moms

Hannah,personally I think if you are climbing on the playground then sandals - baring your toes - are probably a safety issue? Plus wouldn't you get all the wood chips stuck in your sandals? I think playgrounds might call for something more like gear. I do think it's okay to wear gear when a situation calls for gear! For example, if we are going on a long walk, with intention to work up a sweat (i.e., exercise, not just an urban stroll), then I will wear gear. If we are going boating, there's no way I'm wearing anything BUT gear. (Have you seen the Charles River lately? It's not very clean! DH fell in once, and wound up covered in slimy oily stuff.... )

I handwash my sweetpeas - they can run, so you have to do them separately or with like colors. But the good news is they dry super fast. Yes, they make sleeveless versions.

My best bet for machine-washable tops that have some interest - and often some structure - is ATL. I have great luck there for blouses that are made of woven cotton, so highly breathable. My only peeve is that they don't last all that long. You do have to replace them after two seasons or so (realistically -just as you would with Gap tees). But, that shop is cheap, esp at sale time. I will say that their basic cotton tees tend to last better than the Gap tees, and have more interesting details too. They have a bit of spandex in them, so I think that helps them keep their shape better. I also agree with whomever mentioned H&M!

Ultimately I am resigned to the idea that summer tops are something that needs to be replaced frequently. You simply sweat too much in them.

Hannah, thanks! I agree that my outfit was for cooler days-- it was actually surprisingly cool that day. It gets just as hot here in Texas-- triple digits. For that weather, I would wear clams and an interesting sweet pea like top and gladiators. I have a pair of casual white gladiators that I feel comfortable in at the playground. Shiny is right about sandals on the playground-- my feet get awfully dusty. But I'm with you in that I'd rather my feet be dusty than hot.

Sweet pea tops do hold up from washing. I wash my sweet pea tops on delicate and then lay them out to dry. It's as easy as pie for me. I have a separate laundry basket for myself that I put just my clothes in. Then once a week I put everything in it on delicate and skip the dryer. I am in complete control of the laundry machines in our house, though.

I have also accepted what Shiny says-- summer tops don't usually last more than a season for me. There are casual woven machine washable tops out there-- that's often what I look for too. Stock up at the end of the season this year!

Shiny, I think you have a wrong image of Israeli playgrounds We don't have wood chips - I am guessing the reason is that we don't have enough wood to waste it on playground cover, but I might be wrong. Instead, we have some kind of a black rubbery surface (softer to fall at than on concrete). I remember Boston playgrounds - wood chips and grass all around, and trees giving shade. Here, there is no grass - grass needs to be planted and watered, and because of the scarcity of water nobody waters the grass. So, there is this rubbery surface and no shade except from the neighboring buildings. About safety in sandals - hmmm ... I never thought about it, to be honest. The kids are wearing sandals, and they are engaged in a far more intensive physical activity, so I guess it is ok?

Shiny, I don't wash anything by hand - even my bras (which I put in a laundry bag and wash on the delicate cycle). My hands are over-sensitive to detergents and water, so if I wash something by hand, I get bleeding cracks in my palms. Not pretty. About wearing gear - this is exactly the problem: on one hand, the type of activity calls for gear; on the other hand, this is still an outing in the city, and we walk around, and go for ice-cream sometimes (add ice-cream stains to the list of hazards for the casual outfit ), so I don't want to wear gear. I guess I am looking for something that is just as comfortable as gear, but doesn't look like gear. Did I say "impossible task" before?

Patience - aha, so the Sweet Pea tops can be machine-washed! I might consider them then and compromise on drying (my initial requirement was that the clothes can be dried in the dryer, but I guess this might be too much for grown-up clothes). And yes, I will definitely stock up on summer tops when the end of the season sales start. This especially makes sense in a hot climate, because the sales start in July, and I can keep wearing the clothes until November.

OK, so I will be looking for two kinds of outfits: (1) tunics/dresses with leggings (I am very skeptical, but I trust your judgment), and (2) interesting knits with clams. I guess I will leave harem pants for another time
Any recommendations for non-gear-but-feeling-like-gear sandals?

Hannah, these are the gladiators I have which I got last year. They are very comfortable to me. I'd buy another pair if they had my size.

http://www.zappos.com/product/7432900/color/632

I would also recommend Born and Naot sandals that have been linked to on other threads as prettier than gear but still feeling comfortable-- I've worn both. There are actually lots of comfort brands that probably have Angie Approved styles.

Patience, I love your gladiators! Unfortunately, I have very very fussy feet, so I predict they won't be happy in these sandals

My usual trouble with Naot is that they are too narrow for me: unlike Birkenstok, they don't offer regular and wide widths, just one width, which tends to be too narrow. Otherwise, I would definitely purchase a pair, especially since it is our local company (it is still very expensive, but the selection is great, and we have many Naot stores around). However, I think they have several types of dressier flat sandals this year, so I might be in luck.

I think the the leggings and tunic look will suit you, Hannah!

I was also thinking of Naot sandals for you. I think the Allegro line is supposed to run a little wider; maybe something with a backstrap like this one:
http://www.naot.com/cgi-bin/sh.....WMnSandals

I also find Mephistos to be comfortable, but perhaps they would be too narrow for you. Do sandals with adjustable top straps work for you?

I think the casual part is pretty easy for me, at least once I got my wardrobe in check anyway. I had to really focus on what I needed for my lifestyle. I remember feeling like I had an entire closet full of orphans not very long ago actually. It's amazing what all of the wonderful advice on this site, a little perspective and some focused shopping can do for you. I wear pants or shorts (bremuda's most of the time), <cringe cringe> regular shorts on a hot hot day. Then, add simple knit tops (I prefer a rayon blend). Then, my favorite part is fun accessories & shoes!!! They can make or break an outfit for me! I typically am wearing a small heel to work right now & flats for errands during the day. My kids are older to so I don't have to worry about scrunching on my top from holding little one's anymore or spit up. When I did, I used to wear cotton knit & ironically preferred patterns as they didn't seem to show a stain as much. I think I'm leaning more towards solids now from one of Angie's previous blogs as I look back on my wardrobe & think that I likely tire of prints easier as well unless it's a pattern/color I absolutely LOVE (scrolls, paisley, something like that). I also find that I have a tendency to shrink something a bit too much in the dryer sometimes so I have to take that into consideration in my shopping. Gosh, I'm probably digressing now. Anyway, I don't think casual is hard. Dressing up more is probably harder for me.

I like the thinking on this thread and I think I’ve answered all the quezzies - but let me know if I haven’t. A few people hit the nail on the head: change your current dressing habit and lots of practice. It all becomes A LOT easier after a few tried and tested seasons. Promise!

So, HannahC, you have ample feedback to get the search going. I eagerly await your progress. And on that note, have you considered stylish Birkentsocks, Naots, Eccos or Merrels?

Unfortunately ladies, the older and softer our bodies get, the more structure we need to look our best. There is no getting away from it. That’s one of my mantras: you need to dress a little smarter as you get older. It’s totally age appropriate. You can still be casual, just WITH style, and that might mean a new type of casual then what you're used to. The goal is to look "youthful" as opposed to "young". Hope that makes sense.

Cciele - I love the sandals you posted! My usual problem with the width of Naot is actually the footbed - in their more classic lines, the footbed is contoured (like in Birkenstoks), but it is too narrow for me, so the edges of the footbed dig into my foot. But, this newer line doesn't seem to have such a contoured footbed ... Must go check them out. The backstrap is a must, because otherwise they will fall from my feet on the playground.

Angie - yes, I will start with Naot, since it is our local brand. I have a pair of Birkenstocks, from before-YLF, and while they are not hideous (this is a Madrid line, they have quite a delicate strap in front), they are very worn already, and also they don't have the backstrap. Anyway, I think Naot are a bit cheaper here.
And you confirmed my suspicions about taking the casual up a notch. So I guess I won't be able to get away with a fitted tee and a pair of walking shorts anymore ... I do need structure, and this is exactly what bothered me in dressing casually - the lack of structure, and as a result, highlighting every lump and bump and making me look frumpy.

Now I recognize another underrepresented retail niche - structured casual clothing for women above 35, who are moms of young children Especially now, when the average age of having kids is so much more advanced than in the previous generation (example: my mom was 26 when she had me, and this was considered almost too old; I had my oldest daughter when I was 26 as well, and I was the youngest mom in the daycare and on the playground ).