If you consider yourself a classic dresser, the chances are denim is always on your roster, whatever the weather. Because it's true that a good pair of jeans is totally transseasonal, and can take you from spring (paired with a white shirt and a trench coat) into summer (with an oversized tee and sandals) and then, autumn.
The key to September dressing is all in the footwear, imo. Gone are the flip flops and open-toes. Instead, chunky socks and dark hues take their place - along with a multitude of ankle boots.
Whatever your jean style of choice - turn-up jeans, barrel leg or mom style - an ankle boot is a sure fire way to autumn-proof your denim. Go for a black or brown leather for stomping around at the weekend, or a more fun croc style to dress up your jeans and a nice top. More style inspo, this way!
Lean into Western
Thanks to the likes of Beyoncé and Taylor Swift, cowboy-core is a big trend this year. But if you don't want to go for full-on cowboy boots, how about leaning into the Western look with some brown leather ankle boots to pair with your denim? Look out for buckle detailing and a block heel.
Say yes to suede
Another thing that's really kicking off for A/W 2025 is suede, and this outfit has the trend on lock. But if you don't want to go all out with a trench, how about nodding to the trend with a boot? This dark brown pair are super versatile and can be paired with essentially any denim wash. Just don't forget to weatherproof them!
Don't be afraid to experiment
Neon green? Croc print? Square toe? Tick, tick, tick! This look proves ankle boots don't always need to be black or brown, and you can have a bit of fun with a more outrageous shoe choice. It does help to keep the rest of your outfit more simple - like this indigo blue and black trench 'fit - so they can really sing.
Everyone's clicking on...
Elongate your legs
Fashion isn't always about dressing for your body type - in fact, you can wear whatever the f*** you want. But if you do want to channel your inner Alexa Chung, wearing black jeans with black heeled ankle boots can help to elongate your legs, because it stops the eye from cutting the body off at any one point.
Get to the point
A black pointed boot is always a yes in our book, especially when paired with a deep blue wash denim. The colour blocking of this 'fit also really helps to balance out the oversized coat and jeans, while it also leans into the unexpected red theory. A pop of colour always a good idea!
Reach for a Chelsea boot
Chelsea boots are classic for a reason, and paired with jeans, they really do make the perfect outfit formula. Opt for a slightly wider leg fit than a cigarette or skinny jean, and to channel this outfit try to ensure there isn't a gap of skin between the end of your jean and the start of your boot. Or, add a layer of interest by letting a little coloured sock peek through.
Consider your jeans and ankle boot looks, sorted!
Dusty Baxter-Wright is an award-winning journalist and the Entertainment and Lifestyle Director at Cosmopolitan, having previously worked at Sugarscape. She was named one of PPA’s 30 Under 30 for her work covering pop culture, careers, interiors and travel, and oversees the site’s Entertainment and Lifestyle strategy across print, digital and video. As a journalist for the best part of a decade, she has interviewed everyone from Louis Theroux and Channing Tatum to Margot Robbie and Ncuti Gatwa, while she has also spoken on Times Radio and BBC Radio. You can find her on Twitter and Instagram here.
