My In-Between-Season Wardrobe Is Getting a Little Boring—5 Legging-and-Boot Outfits I'm Hoping Will Change That

As a millennial, I have a long history with leggings. In the early 2000s, they were a casual staple, often paired with ballet flats, oversized tunics or—dare I say it—UGGs.

Whilst they may have faded into the background for a few years, leggings are back in full force, and this time, fashion insiders are styling them in much more elevated ways. The key to chic styling? The perfect pair of boots.

I've seen it everywhere—at home in London as well as in Paris on a recent trip. From what I've witnessed in London, fashion editors and influencers are going very streamlined and classic, with tailored coats and leather knee-high boots paired with sleek leggings. Meanwhile, in Paris, the looks feel a little more nonchalant—stirrup leggings are being styled with Chelsea boots and even bomber jackets, which appear effortless and understated (the objective of the French-girl aesthetic). Whether worn for a coffee run or a night out, it’s clear that this combination is a go-to formula for fashion people right now.

This season, designers have embraced the legging-and-boot duo in fresh and modern ways. The spring/summer 2025 runways saw Bottega Veneta showcase leather leggings tucked into knee-high boots, reinforcing the idea that the comfy basic can be just as polished as tailored trousers. Meanwhile, Max Mara leaned into the power of an oversized coat paired with sleek ankle boots and high-waisted leggings, proving that this once-casual staple can now work across multiple aesthetics.

I've always gravitated towards the effortless appeal of leggings, particularly when styled with knee-high riding boots and an oversized jumper—a look I return to year after year. But recently, I've been drawn to alternative boot styles including pointed toes and heeled ankle boots that give leggings a more sophisticated feel. Whilst UGGs and ankle boots have long been classic partners for leggings—particularly in the early-mid '00s—it's the rise of structured styles—such as sharp pointed-toe ankle boots and the aforementioned polished leather knee-highs—that's solidifying this combination as a go-to for stylish dressers.

The beauty of leggings lies in their versatility (and comfort, of course). Whether you're aiming for a polished office look or a relaxed weekend outfit, leggings and the right boots is such an easy and chic option. Hailey Bieber and Rosie Huntington-Whiteley are firm fans of the combo, often spotted in legging looks—a fitted turtleneck with black knee-high or sleek kitten-heel boots is a go-to for both—showcasing the timelessness and ease of the pairing and underscoring how effectively leggings create a streamlined silhouette.

If you want some more inspo, read on for five boot-and-legging outfits that'll keep your in-between-season outfits in check.

Shop Chic Legging-and-Boot Outfits:

1. Knee-High Boots + Trench Coat + Leggings

Style Notes: A timeless pairing that never fails. Knee-high boots add sophistication to simple leggings, whilst a classic trench coat keeps the outfit polished. This look is perfect for transitional weather and can easily be dressed up or down.

Shop the Look:

MANGO

Oversized Trench Coat With Lapels

A structured, lightweight trench that layers effortlessly over leggings.

H&M

High-Waisted Leggings

These high-waisted leggings provide both comfort and a flattering fit.

Toteme

Belted Leather Bucket Bag Bark

Toteme's minimalist design aesthetic shines in this tote.

Missoma X Lucy Williams

Chunky Medium Entwine Hoop Earrings

These mixed metal earrings are so chic.

2. Riding Boots + Scarf Coat + Leggings

Style Notes: Channel equestrian elegance by combining structured riding boots with a tailored scarf coat and high-waisted leggings. This look is all about remaining grounded in comfort.

Shop the Look:

Toteme

Embroidered Scarf Jacket Camel

This refined coat featuring an integrated scarf is on everyone's wish list.

The Row

Woolworth Pant in Scuba

A lot for leggings, yes, but these are made from stretch ponte for a close and comfortable fit. They also hit the mid-waist at the perfect place, offering a sleek silhouette.

Classic riding boots crafted from premium leather.

MIU MIU

Round-Frame Acetate Sunglasses

Round-frame sunglasses instantly make an entire outfit that much chicer.

CHLOÉ

Marcie Mini Textured-Leather Shoulder Bag

Matching tan tones really solidify this look.

3. Chelsea Boots + Bomber Jacket + Stirrup Leggings

Style Notes: This season, stirrup leggings are having a moment, and the best way to style them is with chunky Chelsea boots and a structured bomber jacket. The juxtaposition of sporty and sleek makes this outfit both practical and fashion-forward.

Shop the Look:

SACAI

Shell Bomber Jacket

A slightly oversized bomber for a modern edge.

LESET

Rio Stretch-Ponte Stirrup Leggings

The stirrup elastic ensures no pulls or fabric bunching at the top of your boots.

& Other Stories

Lined Leather Chelsea Boots

Chunky soles add an effortless cool factor.

& Other Stories

Paneled Leather Bag

We're sticking with the casual, hands-free, errand-day vibe with this look.

Celine

Triomphe Oversized Square-Frame Acetate Sunglasses

4. Mini UGG Boots + Blazer + Leggings

Style Notes: The return of mini UGGs has made this look a favourite amongst fashion influencers. Paired with a structured grey blazer and classic leggings, it's the ultimate mix of comfort and structure. The contrast between the soft UGGs and the sharp blazer creates an outfit that feels intentional yet laid-back.

Shop the Look:

H&M

Oversized Single-Breasted Blazer

A versatile blazer you'll get so much wear out of.

ZARA

24/7 Regular T-Shirt

LULULEMON

Align Ribbed High-Rise Nulu Leggings

A sculpting, high-waisted option that moves with you.

Ugg

Women's Classic Mini II Boot

This viral favourite keeps coming back.

The quilting really adds to the off-duty aesthetic.

5. Ankle Boots + Oversized White Shirt + Leggings

Style Notes: If you're after a minimal, polished look, this is the outfit to replicate. An oversized white shirt paired with ankle boots and classic leggings is so Rosie Huntington-Whiteley-coded. Whether worn for a day at the office or a dinner out, this is a fail-safe look.

Shop the Look:

Róhe

Deconstructed Poplin Shirt in Optic White

Róhe is like a mix of Toteme and The Row, and this crisp white deconstructed shirt proves it.

M&S Collection

Cotton Blend Thermal Leggings

KHAITE

Arizona Leather Ankle Boots

A slightly Western-inspired boot from Khaite with a pointed-toe and small slanted heel.

JACQUEMUS

The Bisou Perle Embellished Leather Shoulder Bag

Brown adds richness and polish.

ROXANNE ASSOULIN

Baby Bubble Set of Three Gold-Tone Bracelets

These look more expensive than they are.