Booties and a dress plus a vest is best

Office Appropriate Outfits - Fall

One of the best parts of having a friend with a shop full of clothing is getting to play dress up when I go over there. A few weeks ago, I was wearing this dress and booties when I showed up at Annabelle’s. I found this awesome duster vest in her racks and immediately put it on.


Dress from Moonfish (similar) | similar booties | Vest from Belle on the Roe | similar necklace

I ended up loving this outfit so much that I borrowed the vest and wore it to a Chicagogrammers outing at Joy District. Amusingly, the style name of this vest is “Joy”. So, yes, I wore a Joy to Joy District.

Thanks to Maggie for pointing that out.


I have not yet added this vest to my closet, but there’s a good chance it will happen. I feel like a vest just adds that little extra something. And when it’s not quite cold enough to break out the puffy vests a lightweight one like this can be that perfect “completer piece”.


In other news, I’m still on the fence about booties and dresses or skirts. But, the more I see other people wearing them the more comfortable I am, In fact, I got a lovely compliment on my booties from another Chicagogrammer so clearly the combo doesn’t look as weird on me as I thought it might.  So, yay for that!

Your thoughts on booties and dresses? I’d be curious to see if they’ve changed since the last time I posted about it.



4 replies on “Booties and a dress plus a vest is best

  1. Dee

    Booties and dresses? I have abhorred them for YEARS. It cuts off the body proportions, making us gals look short and stubby, and they take away from the clothing that is worn to be seen and complimented upon. The shoes should be an extension of the outfit, not a “PS” at the end. Save the booties for when you wear slacks.
    As for vests, I totally agree with your assessment of vests. When I was teaching, the rooms were always cold, but I needed flexibility for teaching the arts. Thanks to that, I now have a closet full of assorted vests and I now find myself using them, nearly like jewelry as they add a great finish to every outfit.

  2. Maggie

    This outfit is adorable! You must keep that vest!!!! As you know, I have a similar black/white vest, and I almost wore it over a black knit tank dress this past weekend. So now we must wear these outfits together at the same place. I have similar colored booties I could wear …

  3. Bethany @ Accidental Intentions

    So, my opinion on booties and dresses apparently has changed since I commented on that post in 2013, but now I think it comes down to what dress the booties are worn with rather than the concept as a whole. I still think the heels look better with the dress from your post four years ago, but I think booties look fantastic with this dress – and I think that’s because this outfit on the whole looks more casual to me than the 2013 outfit. Or maybe it’s the longer lines in this outfit? The long vest and the longer dress bare less of your legs, so there’s less of a chance of them looking shortened? I don’t know. Point is, I think this looks great, and the booties definitely work.

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