More than any other item in my collection, I find jeans to be the ultimate styling chameleon. They’re the piece I reach for whether I’m aiming to dress up, pare things back, or land somewhere stylishly in between. Each cut offers its own mood: oversized, baggy styles lend off-duty cool; slimmer silhouettes channel ‘90s minimalism; while a great flare seems to transform my proportions, making my legs look impossibly long.
No other jean—nay, no other trouser—creates the same leg-lengthening illusion. Slip them on with a pointed-toe boot, and suddenly your legs appear to go on for miles. It’s a clever trick of proportion: the outward sweep of the flare balances beautifully with the sharp, sleek finish of the shoe, adding height even when you opt for a lower heel or a flat-footed style.
This combination is one of my signature outfit formulas. Beloved by fashion editors for its polish and wearability, it’s a pairing that works across the seasons. For day-to-day wear, I’ll keep it simple with a slouchy tee or a throw-on blouse, but as the weather cools, I swap in lightweight knits and cardigans for a cosier feel. Come evening, the same duo can be styled up with a structured blazer or silky cami with ease.
If you’re looking to invest in a failsafe denim-and-shoe combination that ticks every box, ahead, I’ve rounded up the best flared jeans and pointed-toe boots to try now.
Shop Flared Jeans and Pointed-Toe Boots:
These come in UK sizes 4—24.
These look more expensive than they actually are.
Style with pointed-toe boots or pair with a sleek heel.
This dark olive shade is set to be a major colour trend this autumn.
The flares jeans trend isn't showing any signs of slowing down.
Style these under flared jeans or pair with a miniskirt.
I always come back to Mother for their chic denim collection.
Be quick! These won't stay in stock for long.
The lyocell blend ensures a comfortable fit.
These also come in a rich shade or merlot.
-
Fashionable People Would Like These Fall Trends From Amazon's October Prime DaySee the affordable yet chic finds.
-
Just so You Know, These Are the Cult-Favorite Hailey Bieber Approved Jeans Every Celeb Is WearingSpotted on Kendall Jenner and Dakota Johnson, too.
-
If You Plan to Cuff Your Jeans This Fall, Only Do It With *This* Specific Denim Wash and *These* ShoesEveryone with good taste is wearing cuffed denim this way.
-
A Rich-Looking Closet Is the Vibe—These 30 Amazon Picks Surprisingly Fit the BillSee the affordable yet chic finds.
-
These Are the Best Early Deals of Amazon Prime Big Deal Days—35 Finds That Have My Undivided AttentionShop discounted Adidas, Madewell, Hoka, and more.
-
The Fall Shoe Trend Everyone in Paris Is Wearing With Black Leggings to Runway Shows and Dinners at Chez JanouHint: It's not sneakers or ballet flats.
-
I’m a Senior Shopping Editor—Here’s Everything I Highly Recommend Buying From the Mango SaleGet 30% off just about everything
-
According to It Girls, You Should Only Wear Skinny Jeans If It's This Trend With These ShoesConfirmed by Bella Hadid in Paris.
