Taller boots, from mid-calf and knee-high to over-the-knee heights, are particularly trendy this season. Many of the taller silhouettes look like timeless modern classics to me, especially when the boot fits are tailored and worn with dresses. So, for lack of a better description, I’m calling them Trendy Classics. 

It’s been short boot mania for a decade and, my word, they are awfully practical and much easier to fit than tall boots. Their popularity is understandable. That said, taller boots look fresh by comparison, so by all means dust them off if you kept yours but haven’t worn them in a while.

Here are four colder-weather dress looks with tall boots that look fabulous every season, and might inspire you to create a similar vibe.

1. Sweater Dress and Riding Boots

Combine a sweater dress at a midi or shorter length with casual knee-high flat riding boots. Add a bag, topper, and accessories and you’re done. These boots theoretically go over the knee if you click the link, so imagine that they are shorter and stop at the knee, which is a more common tall boot silhouette. The visual effect when you combine a knee-covering midi with knee-high and over-the-knee boots is the same. If you prefer not to showcase your legs, wearing a midi with tall boots is one way to go.

CHRISTIAN LOUBOUTIN Theophila 30 Stretch-leather Over-the-knee Boots

2. Boho Dress and Western Boots

Combine a bohemian style dress like this tiered boho-lite number here with tall western boots. The shorter hemline is great for Team Legs and showcases the boots, making them as much of a focal point as the dress. Add a bag, topper, and accessories to complete the look if you need layers.

Scotch & Soda Satin-feel Tiered Skirt Long Sleeve Midi Dress

3. Dressy Dress and Dressy Boots

Combine a dressier frock with a pair of dressier knee-high boots and Bob’s your uncle. Dressier boots are usually heeled, but the heels needn’t be high. Dressier tall boots can be the stretchy pull-on type that are usually a better fit for narrow calves. Here, the dress is midi length in that fab ‘70s way, but feel free to raise the hemline.

Boden Elise Pleated Midi Dress

4. Shorter Dress with Over-the-Knee Boots

Combining very tall boots with shorter hemlines makes the boots the star of the show, and draws attention to the legs. The hosiery here offsets the statement of the boots a bit because it accentuates the column of colour. If you want the boots to stand out more, create a higher contrast between your legs, boots and dress. The shirtdress has been belted, which is not essential. Wear it boxy if that’s your preference. Add jewellery, eyewear and watch as desired.

MaxMara Cashmere and Wool Flannel

I have a pair of dressier navy stretch suede boots from Peter Kaiser that I bought in London four years ago. They have one and a half inch heels, which is the highest heel height that I can manage. I’ve dusted them off so that they are ready to wear with some midi dresses the ‘70s way, which I posted on the forum. But first, you will need to get me out of my hi-tops.