As the weather starts to turn and the cold creeps in, ankle boots become an undisputed essential. The beauty in this perennial staple? The right pair goes with absolutely everything. Whether you're a midi dress obsessive or a fan of the classic jeans-and-a-tee formula, you'll soon find yourself reaching for your Chelsea, heeled or lug-soled boots on an almost-daily basis.
There's a specific combination we've been spotting lately that we decided was worth drawing your attention to: cropped trousers and ankle boots. The former is a popular style during the spring and summer months, when we want to have as much skin as possible on show. But it turns out cropped trousers can work wonderfully in autumn, and arguably look even better with ankle boots than full-length trousers. Think about it; the higher the hemline, the more boot is visible.
The proof is in the following looks we've saved from Instagram, featuring ankle-length trousers, jeans and culottes and their perfect boot pairing. You know what to do.
1. Slim-Fit Jeans + Lace-Up Boots
Style Notes: Team slim-fitting jeans with boots that lace up tight to the ankle—this will have an elongating effect and prevent the boots from being swamped.
Shop the look:
As much as I love minimalist style, I'm always drawn to frilly blouses like this.
This dark wash feels smarter than light-blue denim.
Watch out for puddles when wearing these sleek cream boots.
2. Straight-Leg Trousers + Chelsea Boots
Style Notes: Create a laid-back weekend look with relaxed black trousers and a comfy pair of Chelsea boots. Tip: try to have the hemline graze the top of the boot or overlap slightly. This looks a lot sleeker than having an inch of calf on show.
Shop the look:
This is a great throw-on jacket for milder weather.
Ticks-every-box trousers.
& Other Stories' boots are such high quality.
3. Wide-Leg Trousers + Pointed Boots
Style Notes: Cropped wide-leg trousers or culottes look best with narrower boots, ideally featuring a thin heel and pointed toe to balance out the silhouette.
Shop the look:
I'd also style this blazer over an LBD.
Comfortable and polished.
The western-style embroidery completely transforms this boot.
4. Ribbed Trousers + Chunky Boot
Style Notes: You might be used to wearing your ribbed lounge-bottoms with slippers, but try styling them with chunky boots for a cool weekend look.
Shop the look:
On the days when jeans just won't cut it, turn to this super soft ribbed trouser.
An affordable way to tap into the lug-soled boot trend.
Everyone's swooning over this designer-looking Arket bag.
5. Straight-Leg Jeans + Heeled Boots
Style Notes: You'll often find us lauding the versatility of straight-leg jeans, so it should come as no surprise that the cropped kind is just as easy to style. We're wearing ours with heeled ankle boots like Jessica Skye.
Shop the look:
No autumn wardrobe is complete without a splash of khaki.
The perfect straight-leg jeans. Period.
Wear-with-everything boots.
Next Up: 6 Rules French Women Always Follow When Styling Wide-Leg Trousers
-
8 Classic Outfits to Try This Summer If You're a French Girl at Heart (Like Me)Chic.
-
Is It Just Me, or Are Fashion People Everywhere Skipping Sandals for This Cooler Year-Round Silhouette?These boots were made for walking.
-
Summer Is Here! 4 Fun and Incredibly Chic Colour Combinations I've Spotted Fashion People WearingPerfect pairings.
-
I'm Heading to the South of France—15 Outfits I'm Re-Creating to Look Like a LocalEuro summer loading…
-
Forget a White T-Shirt—This Pretty Top Is the Hero of My Summer WardrobeAnd it looks so chic with jeans, shorts and skirts.
-
Sure, Black Dresses Are Timeless, But Everyone With Great Taste Is Wearing Chic Styles in These Pretty Colours This SummerIt's time to brighten up your wardrobe.
-
European Women Have Convinced Me That This Is Spring 2025's Most Elegant Jacket TrendAnd it goes perfectly with jeans.
-
I've Done The Research—These 21 Trench Coats Are The Epitome Of LuxurySpring into action.
