We see plaid skirts in a variety of lengths every season. Wearing them with booties, dressy knee-high boots, western boots, and stompy mid-calf ‘90s boots are several ways pair them with insulating footwear. Since equestrian boots are having a fashion moment, the idea is to pair flat black or brown riding boots with solid and patterned skirts too.
Plaid (tartan or check) skirts in heavier fabrics have an autumnal and wintery vibe. If you have a pair of tall riding boots and a plaid skirt – try wearing them together. Onto some outfit inspiration:
1. Greys, White and Black
A grey and black flared and handkerchief hem plaid skirt is combined with a tight white tee and grey pullover. You can see the white tee peak out from underneath the pullover to create layering interest. A slouchy black bag matches black riding boots and the model’s hair. A slouchy grey beanie works with the palette. A silver pendant necklace adds some shine.
2. Berries, Browns and Cream
A soft and flowing cream and brown plaid skirt is paired with a taupe turtleneck, which picks up one of the browns in the plaid. A guave pink barn jacket with burgundy trim is thrown over the top. It’s mismatched, yet complements the palette. The gingham trim on the sleeves adds a pattern mixed touch. Chocolate riding boots match the brown in the skirt. Add a bag in a shade of brown or burgundy.
3. Sage, Black, Red and Cream
A sage, black, red and cream sequin plaid skirt is combined with a cream welted polo sweater. Its bejeweled buttons add bling to the look. Black riding boots match the model’s hair and the black in the plaid. Add a bag that works with the palette.
4. Navy, Grey, Black and Red
A navy, red, gold and white tiered plaid skirt with asymmetrical hem is combined with a cropped charcoal pullover. Black stompy lug sole boots are the shoes of choice instead of tall black riding boots. Visible pearl grey socks peek out from the top og the boots, which match the beanie. A big bag works with the boots. Add jewellery, eyewear, topper, watch and eyewear as desired.
Of course, feel free to wear tall riding boots with plaid dresses too.



