How to wear stompy boots
The practical gentlewoman. Photos: Andrew Crowley
Stompy boots and sturdy clothes: today I’m channeling Barbara Hepworth in her St. Ives Studio. Or Rosie the Riveter. The Practical Gentlewoman who gets things done; in durable denim, hardwearing workwear and utilitarian clothing. The last time I wore bovver boots was as a Dr Martens-loving student in the 1980s; so initially, I wasn’t sure if I wanted to supersize my shoes once more. But revisiting ‘stompers’ has been a complete revelation. Big boots feel SO right. I’ve barely had the Grenson’s hiking boots off my feet all winter. They’ve become part of an everyday uniform together with a pair of old, slim-leg, black coated jeans, a cashmere roll neck and a big overcoat. For my latest Weekend Style column in the Telegraph I decided to show how to wear stompy boots with a wider, cropped-leg trouser – and ta da! The workwear vibe really works. Functional dressing and a pair of flat boots you can walk in, what’s not to like?
These indigo jeans are from Toast’s collaboration with Blackhorse Lane Ateliers. Made in the UK at the denim brand’s Walthamstow HQ, each pair of jeans takes approximately four hours to make (and costs £225). For similar styles made at a faster pace, try Kin at John Lewis’ barrel leg jeans, or balloon pants, both £79, and COS, high-waisted straight or tapered jeans, both, £69. The matching, longline jacket is a versatile cover-up suitable for a range of different body shapes. As an impromptu wearer trial in the office revealed: three women of varying shapes and sizes gave the Toast/ Blackhorse Lane denim jacket, a whirl and it was a winner every time. Often called a ‘chore’ jacket, other places to find this utilitarian design include: Community Clothing, Everlane, Seasalt, Madewell and Toast has a cotton twill workwear jacket in a selection of colours. And there’s always actual workwear – one of my favourite boiler suits is from the French company Vetra, plus there are plenty of second-hand styles to be found on Etsy.
More chic than stompy
The navy leather, more chic than stompy boots are from Penelope Chilvers. The British brand is involved in a philanthropic campaign with the charity Solar Sisters whereby customers can return their old boots to Penelope Chilvers to be repurposed and then sent on to working women in Africa. The beautiful cashmere jumper in the photo is from Margaret Howell. All items were borrowed for the shoot and returned. The reusable coffee cup is my own. Made from recycled coffee cups, it’s an rCUP, available HERE).
Showing off my boots
Sturdy Workwear and Stompy Boots is inspired by my latest column for the Sunday Telegraph. I’m trying to figure out the best way to share these features – and so wanted to ask you if it’s useful to post something every few weeks as style inspiration (when there isn’t any overlap with what’s on TNMA)? The Weekend Style column is behind a paywall with restricted viewing (though you can sign up, or see all the images HERE). Please let me know your thoughts.
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Discussion (49 Comments)
Thanks for the feedback, Catbird Farm, that’s good to know. Agree with you, stompy boots ARE empowering, I feel like I’m ready for action in mine!
Carey Barnes says:
Ditto to Catbird Farm – so I am also delighted to see whatever you can share here. The only difference is that I am nervous of stompy boots, but with articles like this I could be persuaded.
I always like style inspiration, so any time you can add a little is nice. I’ve been wearing stompy boots all fall/winter with skinny and wide leg jeans, khakis and skirtS.
Claire Cooper says:
Stomps boots for the win. I have a pair of soft leather black platform DMs and they get almost daily wear.
Catharine says:
Ditto on Telegraph content; would really appreciate being able to freely see your fab content. A cheering read in these rather apocalyptic times!
Joyce Morris says:
And ditto again, re the Telegraph.
What’s not to love about those boots, apart from the price. And good to see navy ones too, far more subtle than the, usual, black.
maudie says:
How ‘comfortable in your own skin’ you seem in this fab outfit. The grin on your face in the first picture shows your delight in wearing this oh so Alyson ensemble. Never under-estimate the joy of a good old stompy boot! (Although these are the very chicest of stomper). Your cashmere jummie looks so snuggly and I am very taken with the ‘chore’ jacket – very French.
Thanks Maudie, we shot this in the middle of Storm Chiara – I think I was also happy to be in warm clothes!
Steele says:
Yes, please share your Weekend Style features on the TNMA site. I’m in the US, so not inclined to pay for the Telegraph. The more inspiration from you, the better! As for my stompy boots, they are grey and made by Sperry so are both water-resistant and have non-slip soles.
Amalana says:
Wow, you look amazing in this, Alyson. The colour combination is gorgeous and I love the utilitarian bohemian vibe. I spent the past winter in a similar but more economical version of this; barrel leg jeans from Uniqlo, cashmere sweaters from TK Maxx and Dr Marten ‘Flora’ Chelsea boots. After years of living in skinny jeans, I love the freedom and comfort of wide legs. Especially when wearing thermal leggings underneath, a necessity for surviving winter up here on the chilly east coast of Ireland! Btw I too, would love to see as much of your Telegraph column as possible, as it’s a paper I wouldn’t buy.
Thanks Amalana and Steele, I will share images but I can’t share Telegraph copy so will put together an edit when I can (as per stompy boots).
KikiTotoro says:
I can only echo what others have said – LOVE the vibe in your outfit (“practical gentlewoman” is a great title for a look!) & please do share the styling ideas from your column as the Telegraph is not a paper I would buy, in either paper or electronic form.
Off now to start stalking suitable practical gentlewoman pieces on eBay, Vinted & Etsy!Isobel says:
Fabulous! LOVE the pic of you sitting on the bench! Every sentence of this comment is going to have an exclamation mark! An outfit that suits you to perfection! I don’t have any stompy boots but now I must have some! Can NEVER have enough style inspiration, Alyson!!
Where were these great pictures taken, please?!Oohing and aging over here! Love a stomp boot, it’s an attitude and a style right?
Have several pairs myself… I love vagabond shoemakers.
Those toast jeans and the collaboration makes me proud !
Just wish I could afford a pair !
Ashley xHilary says:
I bought a fab pair of black stompy boots from M&S in October during a boot emergency when I’d left my timberlands elsewhere The M&S ones are fab &I’ve worn them all Winter mainly with skinnies., Me&em sweaters & one of my old tailored work coats. I’ve felt super stylish & very Me as I am now.!
Yes, please share as much of the Telegraph as you can (altho I do buy the paper often for the gardening columns!)
Claire B says:
Love this outfit – I love stompy boots and have practically lived in mine all winter. I love all your style inspiration and the more the better as far as I’m concerned. The Telegraph is definitely not a paper I would buy so I’d love to see that content here.
Corinne Clemson says:
Great to see the UK made jeans featured too. You look great in this outfit but as a petite woman I am really struggling with this wide leg look, if you have thoughts about how we short legged ones can wear them I would appreciate it.
Barbara Hepworth, definitely…with all the creative power that goes with it…
LisaBee says:
Also – stompy, solid boots are just so good for foot health, esp as we age, offering better support for the foot, coverage from injury, stability/balance. Older feet need a bit of something between them and the road. And they look now.
Jane Royce says:
Lovely outfit- the brown and indigo looks great Alyson. Not sure about the crop for someone wider (me).. though I do love the flared leg .. never been a fan of skinnies. I THINK the pictures were taken in Herne Hill, SE London ..? I’ve had to start wearing wide-fitting flats as I have a sore foot.. hoping it will get better as the choice of wide fitting shoes is dispiriting. I did find a slightly Stompy pair of Clark’s side boots and I live in them right now. Has anyone out there found any brand of nice-looking, soft & slightly elevated boots / shoes / hi-tops that come up v generous width-wise??
I’m not a Telegraph reader or subscriber , but would love to see photos of the content of your column Alyson .. am I right in thinking we can’t read the text unless we subscribe?Hi Jane, I think you have access to a couple of Telegraph articles without subscribing – and pictures are in SE London.
Alysen says:
Jane, you may like Andia Fora, which is an Italian brand, and very edgy. I have wide feet and the boots and trainers are bliss from the moment I put them on. Unfortunately they are quite expensive, but patrol The Outnet and you’ll probably be lucky.
Alysen THANK YOU! Googling ‘wide shoes’ is not very inspiring, so it’s great to have that info.. I’ll go on the hunt …
I did actually buy some rather nice white leather sneakers from Clark’s in a wide fitting – part of their unstructured range.. in case you or anyone else is looking for something similar.
Maggie Alderson says:
reading this wearing my new Doc Martens Chelsea boots… like you, my first pair of Docs since the 80s and I’m absolutely loving them. I wear them with my jeans hack: I buy cheapo ultra-dark denim skinny jeans (with minimum Lycra) two sizes too big, then belt them in, chop them off at the ankle and leave to fray. It creates the classic peg shape and people are always asking me where I get my jeans… Morrisons, most recently! xxx
Wow, love your inspirational and yet economical approach to ‘cool-dom’. Might just copy you – see you in Morrisons!
Karyn says:
You’ve inspired me to wear stompy boots (found similar ones to your Grensons at TJ Maxx, even bought another pair for a spare) and I’ve enjoyed them all winter. Love the beautiful sweater, it’s a gorgeous color against the blue jean. I’d enjoy reading as much as you can share here on your blog.
mrsglimmer says:
Another inspirational outfit, Alyson! Nailed it again. Yes please, do share your Telegraph content with us, as I never tire of your posts on style., and wouldn’t subscribe to the newspaper. M & S do a nice utility jean just now – slightly cropped which is ideal for those of us not blessed with your height! Couldn’t resist them in khaki…..
Ditto all the above – I’ve lived in some stompy boots I bought from M&S that I saw raved about online and they are my go to boot – look great with maxi skirts too. I LOVE the ‘practical gentlewoman’ vibe too it sums up exactly how I want to look. If you’re able to give us access to all the looks and advice in your Telegraph column here that would be amazing. Also, cheeky enquiry, but I often wonder what size you are as I think we’re a similar height but that I’m possibly a size or two up from you but I often think I could wear a lot of your looks. I’m 5′ 10″ and a size 12 and a bit pear-shaped (which I suspect you’re not?)
Hi Tessa, yes we are the same height and size – I’m sort of a 10/12 on top (depending on the brand) and 12 on the bottom so a bit pear-shaped, too.
Thanks so much for that – gives me the confidence follow your lead more often. Whist I’m 5’10” I have a long body and have recently taken to wearing high waisted jeans/trousers and feel they work well to make my legs look longer but occasionally feel they emphasises the ‘peariness’ of my shape. Would welcome your view on the high-waisted vibe!
Love the color combo! And you look great in everything you show us! I’m happy to see you in that sweater because I recently bought one exactly the same, except for the color, and I found myself wondering if the neck looks silly on me. It looks great on you, and I love it, so now I’ll wear it confidently. Not so sure about hefty boots. Love them on you (and everyone else), but my big feet are used to small, flat tennies (old-fashioned Keds, in fact). As always, thanks for all the inspiration!
Great look, as usual, Alyson. I have chore jackets in cream and navy that I bought in a Midlands market about 25 years ago (£15 each) and they come out without fail every spring and autumn. I like the Penelope Chilvers boots too, a bit daintier than DMs for those who are more petite.
MaureenC says:
Ditto here too re the Telegraph, never going to see your column unfortunately but respect that you need to earn a crust. So sharing a bit here will be great.
Also I’ve been around long enough to know that the people who work on papers don’t necessarily share the views of its owners or indeed most of the readers. I’ve known people who’ve worked on the magazine bits of the Mail whose politics would give most of the readers apoplexy!Lisa says:
This exactly silhouette has been my winter uniform. I’ve done it by rolling up UNIQLO’s U wide-legged jeans, wearing a skin tight turtleneck from The Kit or Dries van Noten with a cropped Madewell denim jacket over, and Timberland boots. It is so easy, so comfortable, and yet makes me feel so damn edgy. Now I’ve gotten some white jeans in the same model, and hope to continue with a cropped tee and platform sandals for warm weather;).
Alex says:
The practical gentlewoman who gets things done.
I now have a personal definition! Finally – after 48 years of life and THIS look!
Thank you. Wonderful.
Jackie says:
Great article and timing just perfect for me. Recently bought my first pair of soft topped DMs (I’m 65!) and have loved wearing them. I’ve even worn them with longer pleated skirts that I hadn’t worn as my footwear wasn’t not right.
I’ll await the other week end articles. That would be a great help.
I’m a size 12 on bottom. But can I ask what size you would wear in wider leg trouser/jeans as not sure of the look I just go for?? Any advice most welcomeI tend to size up. I am a generous uk12 but would always buy a 14 and cut the label out! (Buy a size 16 and belt them if you are uber trendy like Alyson!).
Becky Gant says:
Now I need to wear my stompy boots more. As a former DMs wearer too and getting close to 40 (in December) I think I’m ready to reimbrace this look again. Thank you I love the blog and follow you on Instagram. You’re very inspiring.
Lauren says:
Everyone “on this side of the pond” in Canada wear Blundstones for that casual boot look. Not sure exactly who started that but they are very practical, come in many colours, insulated or not, workboot protected toes, etc. I love your bog because it is fascinating to see the differences between Canada and the UK
I mention Blundstones in the Telegraph feature, Lauren. They are really practical and lightweight too.
Mrs Tonia says:
I’m in agreement with all those who would like to read some version of your Telegraph columns. I do manage to read one free per week, which I’ve chosen to be yours, by registering as a potential subscriber. Like many here I’m a convert to the comfort of stompier type boots. As I write I’m wearing an incredibly comfortable pair of old Mephisto boots. Still going strong, non skid soles, great for walking distances and not bad with a bit of black shoe polish and a brushing.
From reading the Autumn fashion forecasts I see that this type of footwear is very much remaining on the scene, practical and toughening up the look of whatever one has on.
If it’s possible to present a version suitable for TNMA without excessive additional work, I’d like to read it.To all those who wrote in wondering how to wear wide legged high waisted jeans if not blessed with the height and long legs which Alyson has, the answer is to give it a go. I bought some from Gap two years ago and at 5’5″ if that I didn’t feel happy wearing them out of the house. Now my eye has adjusted to the shape I just get on with wearing them. Boots underneath look better than trainers or other shoes I find. I’ve also got some mid calf denim culottes which look even better on and some cropped wider legged grey flannel trousers. They look very up to the minute and so far have only been worn with boots. When it warms up I plan to wear with opaque knee length socks and chunky loafers instead.
What I love best about my stompy boots (not Doc Martens) is that they have a side zip – so once I have perfected the fit to the my foot with the lacing, I never need to undo them to get them on and off! Though I still often forget there’s a zip and undo the laces anyway. I have a tendency to sprain my ankles so low boots with laces and zips are perfect for me. And I agree that they look great on both wide and narrow jeans legs, cropped or full length.
Sarah says:
I love this look and wish I could wear it myself but there’s something about me that just doesn’t look right in it. My face doesn’t ‘fit’ it somehow – I wish I could work out what it is!
Philippa 
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Would like to see as much of your Weekend Style column content as you are able to share on here as I am not a candidate for a Telegraph subscription – so would never see it otherwise. I am a committed stompy boot wearer myself -they are so comfortable and somehow empowering!