Everyone on My Feed Is Wearing Baggy Jeans—These Are the 7 Shoes They Look Chicest With

If you’re a regularBest Knockoff Luxury Clothing UK reader, you’re probably aware of my long-running love affair with baggy jeans.

Transitional, cool and endlessly comfortable, this once-nostalgic denim silhouette has moved far beyond its ‘90s and Y2K origins, earning a cross-generational stamp of approval in winter 2025. If you're yet to be convinced, it must be said that these aren’t the super-wide jeans made popular by True Religion in years gone by; the baggy jeans of today are still wide, yes, but they have a structure that makes them a little more polished.

However, despite their styling potential, there’s one question that—as somewhat of a baggy-jeans expert—I’m often asked. What shoes to wear with baggy jeans?

Loose, oversized and intrinsically laid-back, baggy-jeans outfits can present a bit of a shoe-styling dilemma. When you've created a look which feels both on-trend and totally you, it can feel slightly deflating when your shoes don’t match the vibe you imagined.

Naturally, trainers complement their relaxed mood, but what if you want to make them look a little more refined? Will a pointed toe deliver the sharpness you're after? What about a shearling-lined boot—does it run the risk of leaning juvenile (the short answer is no)? And loafers are usually a pretty fail-safe option, but do only certain colours work?

Of course, we could look to the runways, as baggy jeans have featured in key collections for a few seasons now. We've seen them paired with chunky boots and tucked into vinyl knee-high pairs; in fact, there's yet to be a shoe combination designers haven't attempted. However, these are hardly the most wearable looks.

Thankfully, fashion insiders have served up plenty of easy-to-replicate baggy-jeans outfits that take the hard work out of styling them for winter 2025. Whether it’s a sculpted pointed toe or a trusty ballet flat (weather-dependent, of course), look no further than the seven best shoes to wear with baggy jeans this season, rounded up for you below.

7 Shoes to Wear With Baggy Jeans

1. Pointed-Toe Shoes

Style Notes: Let's start with the basics, shall we? If there was ever a doubt whether pointed toes worked with baggy jeans, I’m here to erase it. Creating a leg-lengthening illusion, the perfect pair of pointed-toe boots or shoes will make your legs appear to go on for miles. It’s a clever trick of proportion: the loose leg of the baggy jean is balanced out with the sharp, sleek finish of the shoe, adding height even when you opt for a lower heel or flat style.

Shop Pointed-Toe Shoes:

2. Shearling-Lined Boots

Style Notes: Name a better pairing in winter than a baggy jeans and cosy shearling-lined boots. I’ll wait! Delivering comfort and warmth, this combo has been adopted by Gen Z all over my social feeds. But I’m here to prove that this look will work regardless of age. When styled with a statement coat and carefully curated accessories (like a well-placed belt and structured shapes), this look goes from scruffy to chic in a matter of seconds.

Shop Shearling-Lined Boots:

3. Loafers

Style Notes: You needn’t stick to your trusted black loafers this winter; printed and coloured pairs can inject some much-needed joy into dark days. Or, if you have a more pared-back approach to style, non-black neutrals like brown, burgundy and grey can be a welcome change. Take a cue from Hollie Mercedes (pictured above). Her pale grey loafers add enough polish to pull together her cold-weather look whilst brightening it a little.

Shop Loafers:

4. Walking Boots

Style Notes: Comfy denim and chunky boots feel like a cold-weather no-brainer, and now, thanks to gorpcore, walking boots can be cool. Take the Salomon XT-6, for example. A shoe as stylish as it is functional; they keep your feet toasty whilst their durability helps you navigate through tricky terrain (winter in the UK can be a lot on your footwear). Plus, if you're not a huge fan of how your comfiest shoes look, you can drape your jeans over them.

Shop Walking Boots:

5. Clogs

Style Notes: If you've been looking for a way to wear the clogs you bought in the summer, here it is. Cool and easy, these shoes help to ground your look and keep things relaxed. From the Birkenstock Boston to loafer-style hybrids, clogs are the gift that keeps on giving. Take inspo from Rebecca Ferraz-Wyatt (pictured above) and mix playful colours and textures to create a cosy and cute look.

Shop Clogs:

6. Ballet Flats

Style Notes: Depending on the forecast, you’ll still be able to pull out your favourite pair of ballet flats this winter. With a Parisian feel, this low-lift pairing has a nonchalant refinement beloved by the fashion set and celebs like Jennifer Lawrence and Kendall Jenner alike. Dress up or down as you please, styling them with a boho blouse or graphic tee and leather trench—whatever you go for will work.

Shop Ballet Flats:

7. Trainers

Style Notes: Trainers are the most obvious pairing for baggy jeans, allowing you to focus on adding interest with the top half of your outfit. Take Karina's look (pictured above); the addition of a suede chocolate-brown blazer and a cheerful pop of red elevates her simple black bag and trainers.

Shop Trainers: