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.
-
Looking Chic in Cropped Jeans This Winter Means Wearing This Boot Style and ColorElizabeth Olsen would know.
-
Making Basic Jeans and Black Boots Look Elegant Is Easy—Just Add This Coat Color TrendHint: It's neither red, navy, nor leopard print.
-
The 2026 Version of Skinny Jeans Is Here, and I Tried It On—This Is Why It's a Game ChangerThere's nothing dated about it.
-
My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic, Rich-LookingReplica Store FindsEverything is under $150.
-
The "Weird" But Forward Way Fashion People Are Styling Their Sweaters for Fall 2025You'll either love or loathe it.
-
Sarah Snook's New Bag Is So Shiv Roy If She Moved to L.A. and Started a SubstackI'm having Succession withdrawals.
-
My Sister Asked Me What She Should Buy From Amazon—30 Fashionable Items I SuggestedBasically, everything on my Black Friday wish list.
-
Elizabeth Olsen's The Row Boots Are Chic, But These Ones Cost $1360 LessIt's girl math.
