Considering Fall Ankle Boots

I’m not a big boot person. Every year when fashion turns to fall, I tune out on any mention of “Fall Boot Trends.” But this year, the blogs, magazines, and online shops, are like, “BOOTS, get you BOOTS here, OMG why don’t you have BOOTS yet?” It seems the focus on boots is more heightened than normal.

Surprisingly, I’m actually considering getting a pair right now, motivated by the fact that I have a maxi skirt I’d like to transition from summer to fall. None of my current shoes really work with it. Strappy-heeled sandals would look great, but that’s not the most logical choice for fall weather. So here I am considering boots.

I’ve only owned two pairs of boots before that weren’t snow or rain related. When I was in high school, my mom bought a pair of black leather boots for me. They were from Nine West and had a slim wedge heel, almost knee-high shaft, and were quite minimal in design. I thought they were the chicest boots ever. I still think they were quite nice. Unfortunately I wasn’t allowed to wear them to school because we had a no boot policy, but I’d put them on after school and feel grown up, even though I was wearing a plaid, pleated Catholic-school skirt.

Then shortly after college, I bought a pair of brown leather calf-high boots. It was one of my few jaunts into the world of brown footwear and accessories. (Hopefully I’ll never do that again.) They were the slouchy kind and I wore them with a lot of skirts. I’m sensing a trend here.

So my maxi skirt needs new boots to finish off a fall-weather ensemble. But the practical side of me is commanding myself to buy boots that can work with more than a single outfit. Perhaps even with pants. So let’s consider a few pairs that I think might work.

I like this Charley Boot from Madewell. It’s a suede-leather combo with an almond toe. The upper is minimal in design, but the brown stacked heel hints at Western.

This leather ankle boot from Zara is a lot more slick. It has a pointed heel, black stacked heel, and a strap and buckle at the ankle.

Keeping the chunky black heel, the rest of this Nasty Girl boot veers in a different direction. The rounded toe is a bit more “these boots are made for walking,” and the cut out with criss-crossing straps is a cool detail.

Lastly, and maybe my favorite, the Hadley Boot from Madewell is the sexiest of the bunch. Instead of black, wine goes with just about everything. I like the angle of the heel and the fact that this boot is plain of any detailing.


  1. Ellie says:

    I tried wearing boots with a maxi dress last year but I can’t get it to work at all as a look. I do sometimes wear my flats with my maxis, and that seems like a good way to transition them between seasons.

    Last year, I bought purple ankle boots from Aerosoles that had a pointy toe and some rouching and I found myself really loving them. I have skinny ankles, so regular boots tend to do a lot of bunching. I’m thinking of getting some low brown boots this year to wear with jeans (I don’t do brown for work), but maybe something like this – I can’t decide whether they will actually work with skinny jeans though.

  2. Beth Carter says:

    I love the Nasty Girl boots. The straps are great. I am a boot lover, but my boots need to be “made for walking” since I’m on my feet so much for work. I have three pair of black boots. I tried brown once. That was a short lived trend. It did not work for me!

  3. Jessica says:

    Haha Jackie, this made me laugh out loud. First, for the reminder of the “no boots” rule, which I had completely forgotten about. Second, your comment about hoping you never make the mistake of trying out brown again. I’m the opposite. Every time I wear black (even something as simple as a cardigan or a pair of flats), I feel like something is off. I used to be like, “I’m just too blonde and fair-skinned for black! Too much contrast!” – which is an argument that makes absolutely no sense; blonde has nothing to do with it. But when I think about it more I realize I just desire to be as casual as I can possibly get away with at all times (and then I kick myself when I DO have to dress formally and have nothing to wear). I’d be happy if I could wear skinny jeans (and I prefer a medium tone, not too dark), brown boots, and a chunky sweater every day. This is why I love thinking about fashion, because everyone’s style is so different.

  4. Philippa says:

    I love boots! Ankle or knee-high, flat or heeled, they make me feel smart, sassy and sturdy, and can be sexy or cool or feirce or sleek – and sometimes all of the above (although that is a rare boot). My heart went pit-a-pat for those wine Madewell ankle boots, and I would wear them with trousers with joy. But then, I am short, and round-faced, and could not pull off a maxi skirt in winter without looking like I was dressed in someone else’s clothes whatever was on my feet.

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