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What to Wear With Jeans in Winter

I’m sure there is a large number of you who are like, ‘Oh, come on love, we all know what to wear with jeans in winter. What next? Telling us how to tie our shoelaces?’ Also, the correct answer to the question is, as ever, wear whatever the hell you like of course, BUT you’d be surprised by how many messages I get from ladies in a quandary about what footwear to wear with jeans once they can’t do a bare ankle, a secret sock and a trainer.

Also, different styles of jeans just look better with different kinds of shoes, so this article is for everyone in camp two and also anyone else who wants a little bit of jeans inspiration. It’s also another chance for me to show you some of my favourite jeans purchases over the past year or so and how I’ve worn them in the winter months. I’ve added the exact items that are still available and included alternatives for those that are not.


My mother would probably still think this look is a bit ‘Max Wall’, but I really like the pairing of a slim leg (not skinny) jean with classic, timeless 8‑hole DM boots. For all my tips on breaking them in, check this blog here. I might do an update on this soon as currently I find these boots are my most worn because once you’ve cracked the tricky process of getting them softened up, they really are SO COMFORTABLE and they go with so many things.

These Gap high-rise slim jeans come in and out of stock more often than I buy those spicy Japanese rice crackers from Lidl (averaging 2–3 times a week now), so do keep an eye on them for your size to come back as they are, in my opinion, THE most flattering jeans ever. They are sold by waist size. I’m a 12 and wear a 29, if that helps. My jumper is from Zara, but it shrunk first time I washed it so I don’t recommend. When will I learn that Zara knitwear is rubbish?  I’ve found some similar, but better, styles below.

1. John Lewis AND/OR Rachel Stripe jumper 
2. M Hulot Loe leather bumbag 
3. Mango satin quilted jacket 
4. Gap high rise slim vintage jeans 
5. Dr Martens 1460 smooth leather boots 


This photo makes me feel a little bit sad, if I’m honest. Not because I miss that hairstyle (to be fair, it does look nice here and it was definitely a good hair day) but because it was taken in late February 2020 outside my parents’ house, and we ALL know what happened the month after that. I do hope we get those carefree days back again next year. But let’s not dwell on the Covid shitshow; let’s focus on the pairing of barrel-leg-style jeans with hi-top trainers. These jeans are from Cos and they keep going in and out of stock too (you can tell I like the popular choices when it comes to jeans) so I’ve included some alternatives below. Take your regular size in the Cos jeans, by the way.

The green Vejas are sparse now too, but I do really like the tan version. A good tapered jean with a turn up works perfectly with the hi-tops because you can see the whole shoe and you don’t feel like a clown as the width of the jeans balances out the bulky trainer. Hope that makes sense!

1. APC Tina printed cotton sweatshirt 
2. Gucci GG small flap bag 
3. Hush Joely cotton puffer jacket
4. Cos tapered high rise jeans 
5. Veja Roraima nubuck hiker trainers 


Not that you can really see these jeans in this photo, but I just like it and it gives you an idea of how to wear an all-black outfit without feeling too dull. The trick is the accessories. A bright bag and change of laces can make all the difference. Plus a bit of lippy. In my ruthless wardrobe turnover I sold this Sandro jumper and coat a few years ago, but I still try and live by the ‘one-in, one-out’ rule. A classic black polo neck will work just as well and you could change up the beanie hat colour. Ganni do great ones, as do small brand Staple Life (and for only £28).

These H&M jeans are very good for the price; I’ve had mine for about six years. I don’t need to tell you too much about the Grenson Nanette boots, they are timeless. I tend to wear mine more with trousers than dresses these days and I have a multitude of boot laces so I mix it up if the mood takes me. This Amazon store has a great range.

1. Uniqlo +J lambswool cable high neck jumper 
2. Ganni logo patch ribbed beanie hat 
3. Monki classic double breasted coat 
4. H&M straight vintage high jeans 
5. Grenson Nanette black leather and suede hiker boots 


So many people get confused about how to wear trainers in the winter. The answer is easy: socks. In the bleak mid-winter I go for knee socks from M&S. If it’s not too chilly, then a regular ankle sock will suffice. I listed some of my favourite small brand socks on this post (along with a ton of winter boots). These Raey ‘Dad’ jeans work better with trainers than boots as they have a wider hem, thus making ankles appear slimmer. Note on these jeans, size DOWN. Mine are size 28 and I still need to wear a belt. My coat and trainers are old from Sandro, but check The Outnet for a good range of discounted items from the brand.

1. Anine Bing tiger sweatshirt 
2. Hill and Friends slouchy smiley tote bag 
3. The Outnet Sandro double breasted check coat 
4. Raey Dad organic baggy boyfriend jeans 
5. Sandro Flame panelled sneakers 


I’ve waxed lyrical on these jeans many, many times. For me, they are the perfect just-cropped length (I’m 5’7 for reference), good straight leg, minimal stretch, so they don’t go out of shape when washed, and an exposed button fly which, for reasons I do not know, I am always drawn to. They are the perfect jeans to wear with your hiker-style boots as the hem hits just at the top of most boots. I love them so much I bought them in black and white and am trying to hold myself back from buying the new corduroy versions.

1. & Other Stories boxy rib knit cardigan 
2. Cos boxy boat neck top
3. Barbour Mickley quilted coat 
4. Whistles Hollie button front jeans 
5. Shoe the Bear Agda tan leather boots 

I hope this has helped those of you who were asking, and maybe given the others some ideas fir jeans outfits to wear over the coming weeks.

K x

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