Boot reckoning

Canadian winters demand good boots, but flat boots with the right fit that look good with dresses and skirts are so incredibly hard to find. I have been planning to get a pair of riding boots for the longest time now. But after finally saving up to buy an authentic riding boot from Equestrian Collections I discovered even the shortest shafts are too long for me. I suppose nobody really considers how these boots might look with anything other than riding pants. On me they'll definitely go over the knee, but into the territory where they're neither OTK boots nor riding boots. You know what I mean?

So after much thinking I am starting to consider ankle boots. I saw a friend sporting one late last winter, but
her's was more like a bootie with a bit of heel, so I'm not sure how flattering the 1" heel, almost flat ones would be. Logically thinking even with my knee length skirt and dresses they should allow plenty of bare leg, to look interesting. But apparently they make legs look shorter. So I'm a bit unsure.

Here are a few options I've narrowed down. As you can see I'm a sucker for menswear style brogue detailing and cowboy boots. I guess the only way I'll know is if I try on a pair.

1. Frye Carson shortie - Cognac, 2. River Island light brown ankle brogue boots, 3. Asos Aiden leather lace up brogue boots, 4. Frye Carson shortie - Black

Do any of you wear ankle boots with skirts or dresses? How do you feel about them?

**Ahem, I just realized this is the second Fall themed post in the last two days. Forgive me guys, I don't want to pour water on your Summer enjoyment, but I'm just really excited for Fall. :)**

Twinkle Twinkle

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