Bit late to the party here! Like the other fabbers I was expecting a disaster - but the pics show a smart stylish and flattering outfit.

I go to the supermarket often in a rush wearing anything from workout gear to painting clothes to party clothes. I have seen some people at the supermarket in onesies or pyjamas - I cannot get my head around this!

What I do know is when I go to the supermarket in a bad outfit I ALWAYS run into a smart well dressed friend or a long lost ex-boyfriend OR a work client.

What?! This is I think my favorite outfit of yours so far! I love the skirt with the booties. I like the waterfall cardi too. Not bad at all. But 1 is perfection!

But I know the feeling that you are talking about far too well to negate yours! Hugs and hope you feel better soon. And I am sure you were the best dressed in the super market on a Sunday afternoon. Isn't that a good thing? :). The others I am sure went home and thought they should have dressed better!

Alana, the outfit is great! Did your booties hurt because of your mood or are they too snug? If your feet hurt and didn't feel good, the rest of you couldn't feel good either.

Alana this was a great casual outfit!!! Love the skirt, and the stripes on the sweater. I would only scrunch up the sleeves for more structure and bookending bare legs, and may be it wouldn't hurt a bit of a (blocked/sturdí) heel or kind of a low wedge for another pair of booties, for wearing esp for skirts, too. These are looking more of some shooties for me, so much more suited for pants in my book. So, they could be a bit longer up on the ankles, for adding more weight to the top heavy outfit. But pls. be aware it's only my private 2cents.

Then, I so can relate with your hesitation on wearing bare legs with booties in general. I adore bare legs and I love booties. I just can't do them together, with skirts and dresses. esp not if booties are black.(You know? I'm blonde, too!). I wear my black booties(and all the black pumps or flats flats for skirts, too) always(!!) withblack sheers or opaques and so I love them for leg lengthening and adding edginess purposes. Can't help, I just cannot do them together!!!

Hah. I'm chiming in to echo others, Alana. You nailed the outfit and look great. Fantatsic black bookending with the booties.

I think it's more of a question of feeling very out of your comfort zone with this look. Soon that will pass. Rock on. xo

Oh wow, when I saw your WiW on the wall, I thought it was the same exact AT sweater dress that I own. Cool that it is a top & skirt!

I wear mine with a floral scarf -- Angie did a post before about stripes + floral, hence my inspiration. With either bare legs + tall chocolate brown boots, or with opaque black tights + flat black boots or booties. Sometimes I wear with a jean jacket (white or blue depending on my mood) if I am aiming to dress it down.

I think you look fantastic.

I think you look great! (your intro had me a little worried!)
I live in super casual Tucson AZ, where people have their dress up flipflops and sweats and their "casual" ones.....
I tried looking like them, and that wasn't me. Then I dressed as I was comfortable but didn't look like others around me....and people commented--where you going all dressed up????. because it was different than what they were used to. After awhile, people started asking me where I got such cute clothes and now they expect me to look "dressed up" for here, but nice. It may take you a little while to feel okay with your new style, but stick with it, and it will be "your look".....Good luck!

Alana, I got my beret at American Apparel. Not sure if they have those stores in Canada. Be careful if you order online, because you can't return in the store for anything but store credit. They might have other crazy return policies too, so be sure to check. But they have TONS of colors of berets. Mine is 100% wool, which I like; it is quite warm. When winter comes, I put on an alpaca/acrylic headband thingie that covers my ears and the top of my head, and then I put the beret on top of that. Surprisingly, it keeps me quite warm. I live in Minnesota, so my winters aren't as bad as yours, but they are pretty nasty nonetheless. I get severe headaches if I don't keep my head warm, and this combination works well.

I think you'd look cute in a beret!

I know I'm late to this party, but I also wanted to chime in with encouragement. It took me a LONG time to adjust to the idea of booties with bare legs and skirts, and even longer to actually wear it. Now of course it's one of my favourite looks.

One thing I do like, is that if I'm wearing booties with a skirt/dress, is that the booties have a bit of a dip in the front. I find they are less "stumpifiying" that way. Might be worth keeping in mind when you are looking for your next pair, if it's a look you do want to persue. I wore straight ones like yours last year, but this year got the Monroe Robyn's, for that reason. Just a thought.

You go girl!!

nothing went wrong alana you look great!