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 bootschunky 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. 

1. Straight-Leg Jeans + Heeled Ankle Boots


(Image credit: @aida.bdji)

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. 

Shop the look:

2. Leather Shorts + Over-the-Knee Boots


(Image credit: @_jessicaskye)

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.

Shop the look:

3. Leggings + Heeled Tall Boots


(Image credit: @nlmarilyn)

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. 

Shop the look:

4. Black Jeans + Chunky Ankle Boots


(Image credit: @francescasaffari)

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.

Shop the look:

5. Midi Skirt + Cowboy Boots


(Image credit: @venswifestyle)

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. 

Shop the look:

6. Knit Dress + Chunky Boots


(Image credit: @isabellecoheen)

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. 

Shop the look:

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

Freelance Fashion Editor

Harriet Davey is a freelance fashion editor who has been part of Who What Wear's extended team since 2017. She previously worked in print at Look magazine and has since worked across print, digital and social for many other titles, including British Vogue, Stylist, Grazia, Refinery29 and Marie Claire. Also a stylist, Harriet has had the pleasure of producing cover shoots and editorials along with commercial shoots for brands including Boux Avenue, Watches of Switzerland, Benefit Cosmetics and Revolution. To add to this, Harriet also works in live TV styling for ITV’s This Morning. Back to Who What Wear. With hundreds of published stories on site, Harriet knows what the WWW reader wants. Keeping up to date with the latest It buys and runway trends, she can guarantee to keep you one step ahead of the most stylish people. When not writing or styling, Harriet loves to go shopping (yes, more fashion). If she’s not in a local Hackney bar or restaurant, you can find her forever searching for her next holiday destination.