The dos and don’ts of boots

It’s both cozy and cool to pair your favorite riding boots with a tailored blazer and slim-cut jeans.

If you’re going to go for the gold (boots), you should keep the rest of your, um, ensemble simple.

Yes, we know that rainy weather is sometimes fun for your puddle-stomping inner six-year old, but that’s no excuse to wear childish cartoony rain boots. As an alternative, try the equestrian look from slide 1. It’s just as chic (and waterproof!) in the rain as in the sunshine.

A classic rain boot is just as important as a classic trench: Both are timeless pieces you will wear proudly—and stylishly—for the rest of your life.

Yellow boots and a yellow slicker? Not unless your style icon is a rubber ducky. Plaid boots and a plaid sweater? Um, no. Fur-trim boots and a fur-trim parka? No way, Jose, and the same goes for any other matchy-matchy look.

When shopping for a new pair of boots, look for a pair you can wear with everything you own. Choose a neutral color to get the most mileage out of ‘em.

Don’t wear a dress or skirt that hides just the top of your knee-high boots—unless, of course, you are trying to achieve that boots-as-pants look. (Which, last time we checked, wasn’t a good look.)

While the trendy calf-hugging boots can seem scary, if you pair them with a sleek and simple skirt or coat that hits at the knee, they can actually have a sveltering effect.

Bright red boots like these spice up a simple outfit in mere seconds.

Lady, don’t get us wrong: We love your pink boots—we just kinda wish you hadn’t worn pink everything.