Everyone On My Feed is Wearing Baggy Jeans, These Are the 7 Shoes That Look Chicest With Them

If you’re a Who What Wear UK regular reader, you’re probably aware of my long-running love affair with baggy jeans. Transitional, cool and endlessly comfortable, this once nostalgic silhouette has moved far beyond its ‘90s and Y2K origins, earning a cross-generational stamp of approval in winter 2025.

It must be said, these aren’t the super-wide True Religion popular in years prior. The jeans seen today are still wide, yes, but have quite a structure which keeps their zest but feels innately 2025. However, despite their styling potential, there’s one question that—as somewhat of a baggy jeans expert—I’m often asked: What shoes actually pair best with baggy jeans?

Loose, oversized and intrinsically laid-back; outfits created with baggy jeans can often come with their fair share of shoe-styling dilemmas. Naturally, a trainer complements their relaxed mood, but sometimes we crave a look which is a touch more refined. Will a pointed toe deliver the polish we’re after? What about a shearling-lined boot, does it run the risk of leaning juvenile (the short answer: no)? And loafers are pretty fail-safe, but do only certain colours work? I fear we’ve all experienced the minefield that comes with styling a baggy jean. And at times, when we’ve created a look which feels wholly seasonal, on-trend and totally ‘you’; it can feel slightly deflating when your shoes don’t match the vibe you imagined.

Of course, we could look to the runways, as baggy jeans have been making a splash for some time. Paired with everything from chunky boots to tucked into vinyl knee-highs, there's yet to be a shoe-and-baggy-jeans combination that designers haven't attempted. However, as chic as the runways usually are, they can at times lean a touch unwearable. Thankfully, fashion insiders have served up plenty of easy-to-replicate baggy jeans looks that take the hard work out of getting dressed, proving their styling potential goes unmatched in winter 2025. Whether it’s a contrasting pointed toe or a trusty ballet flat (whether dependent, of course!), each shoe helps to elevate your look. If in doubt, look no further as I’ve rounded up the seven best shoes to wear with baggy jeans this season.

7 Shoes To Wear With Baggy Jeans

1. Pointed-toes

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 change your mind. Creating a leg-lengthening illusion, the perfect pair of boots will make your legs appear to go on for miles. It’s truly all about a clever trick of proportion: the outward sweep of the baggy’s balance beautifully with the sharp, sleek finish of the shoe, adding height even when you opt for a lower heel or a flat-footed style.

Shop Pointed-toe Shoes:

2. Shearling-lined Boots

Style Notes: Name me a better pairing in winter than a baggy jean and cosy shearling-lined boot? I’ll wait! Adding comfort and warmth, this pairing cast a youthful silhouette beloved by Gen-Z's all over my social media feeds. But I’m here to prove that this look will work, regardless of your age. When paired with a statement coat of your choosing and carefully curated accessories (think a well-placed belt and structured shapes), this look goes from TikTok-approved to perfect for all in a matter of seconds.

Shop Shearling-lined Boots:

3. Loafers

Style Notes: You needn’t stick to your trusted black loafers this winter. Prints and colours can inject some much-needed joy into at times very grey days. Or, if you have a pared-back approach to style, non-black neutrals like brown, burgundy and grey can be a welcome change. Take cues from Hollie Mercedes look, her loafers add the right amount of polish, pulling together her cold-weather look rather than distracting from it.

Shop Loafers:

4. Walking Boots

Style Notes: Denim and chunky boots feel like a colder-weather no-brainer. With gorpe-core trending, shoes laden with practicality have become the fashion set's go-to this season. Think Salomon XT-6’s, a shoe as stylish as it is functional; they keep the chill at bay, whilst their durability helps you navigate through ever-changing terrain (winters in the UK can be a lot on your footwear). When paired with baggy jeans, they create a look laden in functionality. Now not everyone want these boots to be seen, but here in lies the magic of a baggy jean. The draping effect of will hide their robust nature meaning they’ll pair well with every colour or style of denim you choose!

Shop the Look:

5. Clogs

Style Notes: We’ve loved pointed-toe mules this summer, so why should winter be any different? Cool and super low lift, these shoes help to ground your look without drawing the eye. From the Birkenstock Boston to a plight of shearling-lined iterations, clogs are the gift that keeps on giving this season. Take inspo from Rebecca Ferraz-Wyatt and mesh playful colours and textures together to create a look perfect for the season ahead.

Shop Mules:

6. Ballet Flats

Style Notes: Weather dependent, you’ll still be able to pull out your favourite pair of ballet flats this winter. With a Parisian zest, this low-lift pairing has an innate refinement beloved by the fashion set and celebs like Jennifer Lawrence and Kendall Jenner alike. Dress up or down as you please, from a boho blouse to a graphic tee and leather trench. Each pairing oozes a polished finish perfect for winter 2025.

Shop Ballet Flats:

7. Trainers

Style Notes: Now, trainers and baggy jeans are a combo that never dates. Balancing a laid-back edge to elevate focus on the top half of your outfit. Take Karina's look, the addition of a warm chocolate brown suede blazer and a cheerful pop of red adds a casual refinement, elevating her black bag and trainer combo with ease.

Shop Trainers: