From Leggings to Jeans, These Are the Best Basics to Wear With Boots

Aside from a new winter coat, there is little that gets us as excited as new boots. The thing is, though, as much as we love boots, they can often result in some tricky decisions. By the time you’ve made up your mind whether you’re going to opt for knee-high boots, chunky Chelsea boots or this season’s key style, cowboy boots, their versatility means we then have to rack our brains for what to pair them with. When these moments hit and I find I have too many boot outfits to choose from, I always head back to basics. 

Be it a pair of comfy leggings elevated with a pair of glossy knee-highs or your favourite straight-leg jeans that sit just over your new pair of ankle boots, classic items are sure to take all the stress out of getting dressed. To make things ever easier for you, I’ve compiled six boots-and-basics outfits that just work so well. The best part? With these easy outfits needing minimal effort, you can hit snooze one more time on these chilly autumn mornings. Ten more minutes in bed and a stylish look? We’re sold. 

Style Notes: Queen of wardrobe staples, Aïda is of course one to follow for effortless styling tips. Here, she gives a lesson in wearing your straight-leg jeans with heeled ankle boots. As with Aïda’s look above, your jeans hem should fall slightly over the top of your boots so not to flash any ankle, and I often opt for slightly taller ankle boots to help with this. Add cosy separates for a polished yet weather-appropriate look. 

How beautiful is this wool coat? It’s one of the best I’ve seen on the high street this season.

These jeans are loved by editors, influencers and celebs. I love the perfect blue wash.

Get Aïda’s look with these nude, lace-up boots.

Style Notes: Who What Wear contributor Jessica Skye always manages to make basics look trend-led. Combining simple leather shorts with more weather-appropriate, suede over-the-knee boots is an easy way to make shorts work for throughout the chillier seasons and beyond.

I don’t think I’ll ever tire of this striped sweater, which is the exact same as the one Jess has on above.

Leather shorts might not be the first thing that comes to mind when you think of wardrobe basics, but I’m here to tell you they’re so versatile. I wear mine with tights and an oversized jumper in the week and heels and a blazer on a night out.

Suede boots are just so chic. Need tips on how to care for them? Read our handy guide.

Style Notes: The epitome of comfort can be delivered by a great-quality pair of leggings. For an easy yet elevated look, add a sleek heeled knee-high boot over the top, just like Marilyn did. And make sure you keep the vibe polished rather than sofa-ready by wearing with a more premium jacket and accessories. 

This padded jacket will add a stylish twist to your legging look.

As expected, Spanx does some of the best leggings around. These are comfy and, thankfully, not see-through.

Ah, Zara. You never fail us when it comes to sensationally good boots.

Style Notes: A classic autumn/winter outfit combo that’ll never fail is a trench coat with black denim and chunky boots. Francesca looks so cool in her pair from The Row, and I love how she’s added a cap for extra preppy points.

For affordable cashmere, head to H&M. 

A wardrobe classic you’ll love for years.

These jeans go up to a size 4XL. I love how they look with heeled mules.

Boots to get you through all kinds of weather.

Style Notes: Let’s just start by saying there’s no better autumn/winter combo than a midi (skirt or dress) with knee-high boots. The fail-safe pairing never fails to look put together, and Renia shows how to make it feel fresh with a graphic knit and white cowboy boots. 

This knit will look just as good with jeans and leather trousers as it will with a midi skirt.

Wear this at the weekend, to the office or on date night.

These boots are just incredible. I love them with jeans tucked in as above, too.

Style Notes: The knit dress has secured its place in most capsule wardrobes by now. With iterations that can be adapted to each season, for autumn, it’s all about cosy, slouchy styles. The fact is, they look great with any boot going, but Isabel makes a case for the thick-tread stomper boot we most likely all own from last year. 

By Malene Birger’s knitted dresses have earned themselves cult status thanks to their popularity amongst influencers and editors alike.

An amazing belt can instantly transform a look.

A classic style that can be dressed up or down.

Next Up: 8 Elevated Staples That Are Guaranteed to Make Your Autumn Outfits Look Polished