Last winter, I was inspired by a Pinterest pic to pair a structured A-line skirt with an oversized sweater and over-the-knee boots and it became one of my favourite outfits ever. (You can see that outfit here.) It was fun and cozy and made the winter a little brighter. So when I found an amazing oversized sweater in my favourite taupe-brown hue at Winners last week, I knew I had to try the look out again.
Skirts and sweaters go so well together, but we tend to see more fitted styles paired. But I love how unexpected a skirt and a purposefully oversized sweater looks, particularly when you dress it up with sleek heeled boots or booties and a smaller handbag. (I wore the same Rebecca Minkoff bag with both looks because it’s small size is a great contrast to the oversized sweater.) I did wear tights with both looks because the previous post was from the dead of winter (January) and it was pretty chilly on the day I shot this look. But when the weather warms up a bit next week, I’m definitely trying this sans tights, and maybe with a favourite black cashmere sweater that also fits slightly oversized.
A simple black skirt gives you lots of versatility in terms of what type of sweater you wear with it, from stripes to bold colours, to understated neutrals. My structured satin skirt is an H&M find from last year, but there are so many similar styles available this fall, including from H&M, which you can see here.
As I mentioned, my sweater was a Winners find (I have found a lot of great pieces there this year), so it’s hard to predict whether you could find the same one (though the Edmonton City Centre location still had some the last time I checked). For those who aren’t in Edmonton, I did some research to find similar styles and have linked them below.
My boots are simply THE BEST over-the-knee boots this side of Stuart Weitzman’s (always and forever on my lust list) – my favourite feature is the fact that they are so stretchy they don’t even need a zipper, yet they maintain their shape and stay up better than any other boots I’ve tried. Honestly, these boots will fit all calve types, from slimmer ones (jealous!) to more athletic ones like mine, so if you have every considered otk boots but have been concerned about them fitting properly, I highly recommend these (and trust me, I’ve tried on DOZENS AND DOZENS of otk boots looking for ones that fit me properly). In fact, my three go-to pairs of over-the-knee boots (see them here and here) are from Steve Madden and they all fit extremely well and come in under the $200 mark, which is great if you want to have lots of colour options in your closet. I did link the investment SW boots I recommend this year, as well as another option that is highly popular with other bloggers.
I owe some major thanks to my little man, who happily snapped some photos of me on this day. Considering he’s seven, he did a pretty great job. With balancing a full-time job, busy home life, and blogging, it is difficult for me to find the time for more professional blog photos, and I will be honest in saying, that fact often stresses me out as a blogger. But I do love sharing real life shots with you, like the ones below and I hope you don’t mind that I share what I can with the crazy schedule I have! We lucked out and found a park on the way home from school that still had beautiful fall leaves, and the local market happens to have a really great brick wall that was fun for this look as well.
I’d love to hear your thoughts on this look and whether you would try something similar or not! And as a little side note, I just want to thank you all for your continued support and for all the love you’ve shown me here on the blog and on IG. ❤
Enjoy the pretty things in life,