This winter, baggy jeans are really simple to outfit, from pointed toes to shearling-lined mules. Explore the seven sneakers that will elevate your favorite jeans this winter by scrolling down.
If you regularly read Who What Wear UK, you are undoubtedly aware of my enduring passion for baggy jeans.
This once-nostalgic denim shape has evolved well beyond its ’90s and Y2K roots to become transitional, stylish, and incredibly comfortable. In winter 2025, it received cross-generational approbation. If you’re still not convinced, let me clarify that these aren’t the incredibly wide jeans that True Religion popularized years ago. Today’s baggy jeans are still wide, but they have a structure that gives them a little more refined look.
Nevertheless, as a bit of a baggy-jeans expert, I’m frequently asked this question despite its stylistic possibilities. Which shoes go well with loose-fitting jeans?
Baggy-jeans ensembles that are loose, large, and inherently carefree can pose a bit of a shoe-styling conundrum. When your shoes don’t fit the mood you had in mind, it can seem a little disheartening to have crafted a style that is both on-trend and uniquely you.
Trainers, of course, go well with their laid-back attitude, but what if you want to give them a slightly more elegant appearance? Will you get the desired sharpness from a pointed toe? Does a boot with a shearling lining have the potential to cause juvenile leaning? The quick answer is no. Additionally, loafers are typically a fairly reliable choice; however, can some colors work better than others?
Since baggy jeans have been a staple of major collections for a few seasons, we may naturally turn to the runways. We’ve seen them tucked into vinyl knee-high pairs and worn with chunky boots; in fact, there isn’t a shoe combination that designers haven’t tried. These aren’t exactly the most wearable styles, though.
Fortunately, fashion gurus have provided a plethora of simple, replicable baggy-jeans ensembles that make wearing them for winter 2025 effortless. Look no further than the seven top shoes to pair with baggy jeans this season, which are compiled for you below, whether you’re partial to a ballet flat or a sculpted pointed toe (depending on the weather, of course).
3 Shoes to Wear With Baggy Jeans
1. Pointed-Toe Shoes
Notes on Style: Shall we begin with the fundamentals? I’m here to dispel any doubts you may have had about whether pointy toes go well with baggy trousers. The ideal pair of pointed-toe boots or shoes will give the impression that your legs are longer than they actually are. It’s a savvy use of proportion: even if you choose a lower heel or flat style, the shoe’s clean, sleek finish balances out the loose leg of the baggy denim, providing height.
Shop Pointed-Toe Shoes:
ZARA
Kitten Heel Knee-High Boots
£60
Easy to use but efficient. Zara is the only place to look if you’re seeking for a boot that looks costly.
COS
Pointed Pony-Hair Leather Mules
£229
These are a timeless style in popular ponytails that are ideal for celebrations.
ZARA
Leather High-Heel Ankle Boots
£70
Additionally, Zara’s assortment of ankle boots is unrivaled.
JIMMY CHOO
Agathe 85 Knee Boots
£1325
These gorgeous croc-effect leather pieces have captured my heart.
Dear Frances
Topo Bootie
£590
All of your neutrals will look good with this shade of Bordeaux.
2. Shearling-Lined Boots
Style Notes: There’s no better wintertime combination than cozy shearling-lined boots and baggy pants. I’ll hold off! Gen Z has embraced this combination, which provides warmth and comfort, across my social media feeds. However, I’m here to demonstrate that this style is appropriate for all ages. This outfit quickly transforms from messy to stylish when paired with a bold coat and thoughtfully chosen accessories (such as a well-placed belt and structured shapes).
Shop Shearling-Lined Boots:
UGG
Classic Ultra Mini Platform Boot
£155
Use a platform sole to prevent your loose jeans from dragging on the ground.
H&M
Warm-Lined Leather Boots
£160
All-weather prepared.
TOMMY HILFIGER
Logo Tape Lace-Up Snow Boots
£90
These boots will be useful this winter, whether you’re on the streets or in the Alps.
UGG
Tazzelle
£145
The Ugg Tazzelle, Gigi Hadid’s favorite, is selling out quickly.
Le Monde Béryl
Dolomite Boot
£665
Before you go outside, mist these with suede protectant.
3. Loafers
Style Notes: Printed and colored loafers can bring some much-needed cheer to gloomy days, so you don’t have to stick to your go-to black loafers this winter. Conversely, non-black neutrals like brown, burgundy, and grey might be a welcome change if your style is more understated. Follow in the footsteps of Hollie Mercedes (shown above). Her light grey loafers brighten her outfit slightly while adding just enough shine to pull her cold-weather ensemble together.
Shop Loafers:
& Other Stories
Penny Loafers
£119
Since brown suede loafers have been so popular this year, why not switch things up with this stylish gray version?
Russell & Bromley
Dalston Clean Loafer
£295
exquisitely shiny.
MANGO
Suede Penny Loafers
£80
These look so comfy.
Bally
Pinar Calf Hair-Trimmed Leather Boat Shoes
£735
This is such an unusual combination of leather and ponytail.
Saint Laurent
Le Loafer Supple
£880
Saint Laurent’s Le Loafer is a timeless piece with a dimpled toe box and a simple design.
