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Caroline Issa photo: Who What Wear

Cropped kick-flares and culottes are terribly au courant but in winter I like to draught-proof my legs. Eliminate a northwesterly up the nether regions, by opting for a straighter leg style. Now the decluttering has begun (one bagful of stuff to charity and counting), I’m finally going to have a go at getting rid of the boxes of ‘fashion editor’ shoes stashed under my bed. Just. In. Case. Just in case I get invited to the BAFTAS. Just in case my bunions stop hurting when I wear them. Just in case I ever learn to walk gracefully in spindly slingbacks and kitten heels. I’ve always preferred flat shoes or boots, and trainers anyway; and I’m sure I’ll feel freer without the Shoes of a Former Life gathering dust and hair balls under my bed.

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In the land of street style, it’s virtually impossible to find inspirational pictures of grown-up women wearing tights or socks and flat shoes but I’ve done my best. Here’s Vogue fashion director Lucinda Chambers:

Lucinda Chambers

And a chic Milanese woman photographed by the Sartorialist (though I bet her feet are chilly in Converse):

Sartorialist, older model

And if you’re wondering about the Great Loafer Conundrum, making an obvious sock statement can work:

Photo: Garance Doré



How are you wearing flat shoes and boots this winter?

PS The leopard print Chelsea boots (above) are asos but the link is misbehaving, available HERE.

43 thoughts on “How to wear flat shoes and boots right now

  1. Great looks with the exception of the vans. Never been a fan of that shoe. Love my flats and boots and kitten heels:)

  2. I wear flats 99.5% of the time…my feet have just reached that point…but I love them and find there are many stylish ways to wear them. I do wear sneakers, but it is rare. I am always on the search for the most comfortable flat. Good topic!

  3. I find this kind of post immensely helpful – showing a nice assortment of wearable styles that will influence my day-to-day choices. Thank you.

  4. Excellent post. I want that lamby jacket.
    I wear flat boots and sneakers with pants. I have taken to wearing flesh colored cotton socks to keep my ankles warm this winter if i’m not wearing pants that intersect with the shoes. I wish I had a couple more inches than my almost 5’5″. It’s a better look with a little more height.

  5. Apart from a couple of pairs of wedges I’m almost exclusively flats these days. Sheep skin insoles help guard against cold toes when socks aren’t an option. Brogues and slip on skate trainers are my go to. I do however struggle with skirts and flats with my short legs

  6. Yesterday I wore doc marten oxfords and pink marl vintage Shetland wool socks……ive never really done socks but I was darn cold…..I like felt grown up and practical

  7. Always boots! occasionaly oxfords (those laced shoes men wear? I love them and wear them since I was very young!). Booties , in leopard, black, swede, green and tan leather. I wear them all trough fall and winter…all flat or almost, the exception beeing a very confortable 5cm heels.

  8. I’m loving a pair similar to the black Steve Maddens above. We have had a lovely winter so far, thus no need for the heavy duty snow walkers I usually sport. The black boots might be a little staid, but oh, so comfortable and versatile.

  9. I can’t wear flats. Need a bit of heel – I think it looks more elegant unless you’re tall and thin. I feel frumpy in flats – a no-no!

  10. I always wear flats and boots now. But I think funky footwear is our saviour and reeks ‘thatisnotmyage’! I have bought a pair of red ankle boots and they look fab with jeans or jeggings. I also love those long, black ‘almost over the knee’ boots I saw my hairdresser wearing. I have brown chelsea boots that go with anything and some lace up bovver-boot style clumpy ones that make me feel like stomping everywhere which feels good.

  11. For those of us not blessed with tall and willowy silhouettes, we need to keep in mind the Italian phrase, la bella figura – and what is the overall effect off heavy winter outer wear and flat shoes. All these women look comfortable, that’s for sure, but stylish… I guess that is for the individual eye to judge.

  12. Oh yes, flats definitely. I wrecked my back wearing heels all the time when I was younger and now flats are a necessity more than a fashion statement. Thanks for showing these options for women with style!

  13. I can’t wear heels due to feet, knee, and back problems, haven’t worn them in years. I’m one step away from being stuck in orthotics. I can only wear shoes that actually fit my incredibly narrow heels or have some mechanism to ensure they won’t fall off my feet — mostly flat mary janes, the rare loafer style that actually fits. Walking Cradles is my savior, they make a few shoes that are actually cute. I don’t like wearing athletic-looking shoes all the time.

    I just embrace it. I walk in comfort, tall (even though I’m short) and proud. I’ve knit an entire wardrobe of colorful socks in various stripes, patterns, textures, ribs, laces, etc. Wool, cotton, synthetics, blends. Since I mostly wear jeans, it works. My slightly edgy socks just become part of my look. With a dress or skirt it’s either tights or boots. If it’s a denim dress or skirt, maybe striped socks over plain tights with ankle boots. In really cold weather, silk sock liners underneath the tights.

  14. I wear flats most of the time (I’m ancient, with dodgy knees) and trousers. I’d love to wear flats and skirts but with a height (or lack of it) of five foot and a fag paper, I look like an escaped Albanian librarian in that garb.

  15. I love all the looks shown here! And although, I still wear my pedestal sitters [4 inches and up!] occasionally– I prefer flats, sneakers and more flats! And the more ornamented the better.

  16. I like the examples very much. Women of our age seem quite divided about sneakers. I prefer flats, sneakers and boots. Heels are for special occasions and then only when I feel height challenged or the outfit demands it.

  17. Have just taken my last bag of heels to the charity shop after saving them “just in case”but as I’ve been doing the boots/flats/trainers thing for the last two years I had to face the fact that I just can’t squeeze my poor little toes into this kind of thing anymore and I do like zipping about these days which is impossible in heels.A few years back I would scoff at the flat shoe people but now I’m proud to be one of them!

  18. I wear only flats now. I have 1 pair of heels for any formal occasions, the rest I donated. It feels somewhat freeing after wearing heels for eight hours a day, plus evenings out. I must find a pair of leopard flats/booties. They take any outfit up a notch. I do like fun socks! Jackie’s idea of flesh colored socks is great for those times when you want that bare foot look but it is chilly out.

  19. I love wearing flat boots – my favourites are my black lace-up paratrooper style boots. So comfy, and I think they make every outfit look cool (they keep the ankles warm too). I wear them with skinny jeans, flares, and even long skirts.

  20. Why oh why would we ladies of a certain age wear anything else!? .When I see older ladies tottering around, obviously in agony I am so relieved to have left vanity behind. However there are some amazing flat shoes around, love the selection here…….long live the flattie I say!

  21. Am wearing skinnies with my new Jimmy Choo biker boots. A sale bargain. Great for shopping and walking. . Also kitten heel Acne ankle boots if wanting a dressier look.

  22. I am in the tall and willowy category at five foot eleven. I generally wear various styles of trousers with flat shoes or boots although this did not stop me falling last summer and breaking BOTH ankles! I am currently at the point of having outpatient physical therapy. When my therapist relays all the horrendous problems women can have and do have from wearing high heels, I wonder why anyone would wear them. They can indeed look wonderful but are they worth jeopardising ones future mobility for style?

  23. As it happens, following my own closet clear-out I have a neatly lined-up row of high heel shoes on their way to the charity shop. I’ve decided that I will never wear them again, and it is better to release them into the wild where they can be enjoyed as they should.

    I wear flats or low to mid heels, but high heels just don’t work with my life any more.

  24. You found wonderful pictures, especially love the Milan one, and the last one, I’ve never tried the converse look, mostly stick to loafers, but, you’ve given me just the push I needed to try out something more sporty, thanks!

  25. I am known as the queen of heels but even I have invested in more flats than ever in the past few months. I will be turning 60 later this year and my feet are starting to remind me of that after a lifetime of wearing heels. I will still wear my heels at night but I am wearing flats more often when I know I will be walking a lot during the day. Great post! I love, love, LOVE your book!

  26. Please do a post on skinnies/narrow straight leg trousers to wear with flats/booties. I am 5’11” and in my late 60’s and love the look but cannot find trousers that are narrow enough on the bottom. Proper narrow trousers, not leggings or the like. Love your blog; always relevant and focused. Thank you.

  27. What length should straight leg trousers be in winter to look stylish with flats? Advice please anyone. I love skirts with chelsea boots or brogues. In summer cropped trousers, no socks, flats or sandals. A post on straight leg trousers and flats would be great. Love the blog and the book. Thanks

  28. Is there any other way to get through Winter than in tights and socks? At this time of year, NO-ONE looks good in bare legs and heels. It’s bad enough, the rest of the year, watching women tottering about in shoes that are quite clearly killing them. Without tights, watching their legs turning blue, it’s worse…!
    Personally, I wear socks AND tights, to prevent my feet sliding around in my boots. This way, I feel as good as I look…!!
    [LOVE the lamby coat, too, by the way!]

  29. I am with Anna K as a short person. So it is boots. Until the weather becomes clement enough to look at my brogues and loafers. I do not do wacky socks as they can make short older women look a little lost. Yesterday it was walking boots due to snow. Today, trainers in case of slippy bits. In the winter, I am not a style icon.

  30. It’s not about the shoes…it’s about the height, stature of the person and the cut of the pants. Slim or closely edited pants look great with flats or heels. Slim silohuette, slim heels, flowly, easy scaled pants, easy footwear. Flat, flats can look too flat depending on your height and body type, a small wedge or heel looks great on average heights and curvy silhouettes, while taller, endomorph type people can carry flat, flats, though ,,tthis shoe choice can tire feet. It’s never a case of this or that, body type, height and most importantly the cut, scale of the pants determine the best shoe choice or choose it, wear it and own it! there’s more to life then pants and shoes-but so much fun!


  31. It’s not a this or that decision, it’s all about the cut of the pant and the stature of the wearer, slim pants look great with flats or booties and fuller, flowy cut pants look great with flats and or booties. You have to recognize your body type, stature and more challenging, to accept your body type and dress for it! If you’re of a smaller stature I think that slim, close to the body pants with small heels or booties look great, more statuesque body types look great with flats or booties too depending on the cut of the pant. I think that a fuller figure with slim pants and high heels can look cheap; pair a slim pant with lower heels or flats and a loose top and the wearer can look classy. Choose what you want to highlight, shoes, pants, cleavage, or an overall pulled together look-nothing seems to stand out, an overall look that suits your body type, activity involved and communicates comfort, lets your personality shine!

  32. Wow – am breathing a sigh of relief …. its not just me… !
    Am at the stage of heels only for occasions (with a pair of sparkly flats in my bag if dancing is required in the evening e.g. wedding).
    Years of heels during waking hours are catching up with me – probably ballet hasn’t helped (pointe shoes look beautiful but are not kind to your feet!!) .
    Giving up heels is breaking my heart especially being 5’2″. So far being sticking to flat ballet pumps/ loafers…… not sure about sneakers… but reading this article and comments I’m feeling a bit braver about taking the plunge ….
    Think I need to ditch heels I can never wear again too! …. Right I’m off to be brave!!

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