If you enjoy wearing rugged flat chunky boots, combat boots, or classic riding boots with skirts — as some of us did back in the ’90s — these looks are for you. The boots can be any height, with zipper or laces, and have lugged soles. They can be any colour and pattern, but solid black stompy boots are the most popular. Black boots also work well when you have black hair and/or wear a lot of black in general.

These outfits range from dressy to causal, and are neutral and earth-toned. Feel free to create similar looks in your own palettes. In most cases the dressy skirts create a jarring juxtaposition with the casual boots, which is the appeal of the combination.

1. Dressy Bomber

In this creative combination a dressy skirt is combined with a very casual graphic tee, which is semi-tucked to hint at a waistline. Tall, flat and black casual riding boots pick up the black in the tee. The sporty bomber is another interesting piece because it’s a casual item made of dressy fabric. The gold matches the skirt and the black cuffs match the tee and boots. The short length of the jacket lengthens the leg line. Beautiful!

Dressy Bomber

2. Columned Layers

This is an extra comfy combination because it combines three very fluid layers. A flared skirt is paired with a loose blouse in the same colour. A jacket in the same neutral is popped over the top to create an elongating column. Black riding boots and toffee cap finish off the look. I’d have preferred to see brown boots to soften the contrast, but the black boots make a dramatic statement. Why not!

Columned Layers

3. Ruffled and Sleeveless

This type of look makes sense in a warm Fall or Winter, when you don’t necessarily need a topper, and you can go sleeveless if you want to. I particularly like the contrast between the ruffled skirt and combat boots. The fluid sleeveless top is an elegant addition, and the semi-tuck hints at a waistline which adds some structure. You can create a low contrast with a darker top if that’s more your cup of tea. Or wear cream stompy boots to match the top.

Ruffled and Sleeveless

3. Sweater Vest and Pencil

Here’s a version with a pencil skirt or tube skirt. Combine it with a shirt, blouse, or tee and layer a sweater vest over the top that matches the top and skirt. Add a pair of stompy boots, a bag to match, and Bob’s your uncle. Here, the black boots match the black in the pattern of the skirt and the bag, thereby pulling things together. They also bookend the model’s hair. Add jewellery, watch and eyewear as desired.

Sweater Vest and Pencil