Now that the weather’s suddenly turned cold, I have lots of questions coming in about what footwear works best with trousers and jeans so it seems like a good idea to write a practical post. The best solution is a pair of ankle boots but you need to get the balance right – as always, it’s best to think about the body in an architectural way and understand the best part of your leg to focus on.

If you have long skinny legs then skinny jeans and the boots that go with them are an easy choice. If, like many of us, you have more ‘sturdy’ legs then straight or wide leg crops may well be your friend because they skim over the flesh, leaving the focus on the ankle – and ankles are a beautiful part of the body. I’ve found that I’ve gradually built up three rows in my dressing room – boots for wearing with cropped trousers, boots for wearing with a skinnier leg and boots that I wear with skirts. It seems crazy but when I take into the account the fact that I’ll be opting for boots on an almost daily basis from now until May, I know I’ll get my wear out of them. So let’s look at the best ankle boots for different trouser shapes – winter 2018

Boots for wearing with cropped trousers

So I’m going to start with a selection of boots to wear with the trouser shape that is still the most on trend, the crop. You can either opt for a classic tailored crop, a more fashionable straight leg or a wide crop. Whichever you choose, the style intelligence is the same. Because you’ve disguised the form of the leg, you’re ideally aiming to hug the shape of the ankle whilst avoiding a flash of winter skin between hem and foot – so you’re looking for a higher cut boot. Last year’s fabric sock boots with the witchy stiletto heel and pointed toe appear to have been a one season wonder, probably because they were so impractical once winter weather arrived. This year a chunky heel is more dominant which is great because it makes them easier to walk in too.

best ankle boots for different trouser shapes

  1. Burgundy suede boots: treat burgundy as a neutral but use it to add a twist to an otherwise neutral outfit. It looks so much more sophisticated than a predictable black pair.
  2. Pearl grey leather boots with chunky heel: the high fashion choice is for white boots but these are just a little less dazzling and with their pearly finish, they would look lovely if you’re someone who likes to wear tonal, soft neutrals.
  3. Smooth chestnut leather boots: the most popular colour for 2018, a warm chestnut is here to stay for a few winters to come
  4. Leopard boots with chunky block heel and insolia lining: leopard ankle boots will work really hard for you. Ponyskin tends to stand up well to bad weather and it lifts an outfit on a dull winter day. These have a comfortable lining and a strong block heel.
  5. Low heeled suede boots in deep red suede: I tried these on last week and they’re made from a lovely soft suede. The heel is a great height and the toe is rounded, the only problem is that they don’t come in half sizes.
  6. Clean black leather boots with slim heel: these are for anyone who dislikes seaming on the front of a boot, an understated black pair with an interesting heel.
  7. Gold metallic boots with wooden heel: I bought a pair of gold boots last year and wore them a lot in December. Metallics, as always go with everything and make you stand out from the crowd.
  8. Black leather boots with soft sock fitting: these are proper leather sock boots (the sock is made from elasticated leather) the best style for an elegant, streamlined ankle and very hard to find.

Boots for wearing with skinnies

Moving on, it’s interesting to see how women are refusing to give up on skinnies, regardless of what the fashion gods say. In high trend circles of course they are an absolute no. The eldest posted an outfit he was wearing to his sneakerhead forum last week – everything was either vintage or high-heat streetwear and he got high approval for it all apart from the fact that he’d teamed it with skinny jeans which were not ‘lit’ (anyone else struggle to keep up with the urban dictionary?). Anyway, regardless of what the youth think, the midlifers are not putting their skinny jeans in the charity pile just yet. After all, many of us have dogs to walk and wellies to wear – I really do think that’s one of the primary reasons for their longevity!

So, if you’re wearing skinnies, you need a lower cut ankle boot. You can either wrinkle your trouser leg where it meets the boot, tuck it into the boot or tuck the hem under -currently it’s all about a sleek line so cuffing is not a good option.


best ankle boots for different trouser shapes

  1. Navy suede boots with pointed toe: why are navy boots so hard to find I wonder? Anyway here’s a lovely pair – a simple Chelsea style with a low heel which tends to be better for your back and your posture than flats.
  2. Khaki patent boots with cutout heel detail: khaki is another great alternative to black, it works with most colours and these are in weatherproof patent with a chic cutout detail at the heel.
  3. Pine green boots with low block heel: my favourite colour for winter 2018, I’m holding myself back from ordering these because I really don’t have space for another pair of ankle boots but I really love them.
  4. Leopard boots with pointed toe and block heel: leopard again – yes I really do think that both a high and low profile pair of leopard boots is worth having, especially if like me, you’re not a big fan of wearing it near to your face but appreciate that it’s sartorial shorthand for chic.
  5. Red suede boots with low block heel: even though it was last winter’s dominant colour, red continues to be strong because it’s a colour that flatters most women and so once they start wearing it, they don’t want to stop.
  6. Oxblood patent Chelsea style boots: as we’ve already discussed, oxblood is a new neutral, these boots have a lovely profile and patent is always a good choice
  7. Flat navy suede Chelsea boots: it’s easier to wear flats with skinnies than with crops. I don’t tend to go for them because they give me backache but here’s a lovely navy suede pair for people who can wear them.

Boots for wearing with dresses

Lots of people get in touch with questions about ankle boots and dresses or skirts. It isn’t a look that I go for often because I have disproportionately short legs and this can make them look even shorter. Plus of course you have the problem of hosiery and what colour to wear. If you have long, slender legs, you can wear tights that contrast with your boots and you will look really striking. If you have shorter, curvier limbs, it’s better to match your hosiery to your boot for the lengthening effect. Either way, you’re aiming for a boot that stops before your calf begins to widen and if it dips slightly at the front, it will be even more flattering. All of these boots will work with skinny jeans too and with very wide-leg crops or culottes which fit into the same category as skirts.

best ankle boots for different trouser shapes

  1. Low rise snake print boots: these are more of a shoe boot than an ankle boot and snakeskin is an even bigger trend than leopard this season. Also available in black or navy.
  2. Red metallic boots: I have these as you know and I love them, they’re such an elegant cut and they look great with skinny jeans or leather leggings.
  3. Smooth black Parisian boots: timeless chic – think of any Parisian style-setter and you can be sure she’ll have a pair of these ankle boots in her wardrobe. They’re one of the styles that I call a wardrobe essential because they never date. If you’d prefer suede try here or here and for patent, look here.
  4. Navy suede boots: here’s an example of the dipped front that has a leg-lengthening effect, I’ve featured them in navy here but they’re also available in black suede.
  5. Brown toned snake print boots: a darker version of snake which is less of a stark contrast with winter colours and it has an on trend chiselled heel.
  6. Grey suede boots with angled heel: elegant grey with an angled heel which is not only a fashion detail but also helps to distribute the weight of the foot.
  7. Red suede boots: more red because they’re a beautiful shape, also available in black which takes us back to the Parisian chic discussed in number 3
  8. Leopard boots: and yes, leopard again for the reason I’ve already given, it’s worth having leopard in every shape.
  9. Wine coloured patent boots: another pair of oxblood boots, you could wear these with black tights and because they’re dark toned, they wouldn’t truncate the leg too much.

But what about shoes?

I know someone’s going to raise this so I’m just going to dive straight in. It’s the dreaded pop sock issue. I think the reason that ankle boots have been such winter staples for the last few years is mainly as a solution to pop socks. And when it comes to wearing ankle boots I’m really fussy about socks by the way – I don’t like it when they show over the top of the boot and until now I’ve always worn the trainer socks that I use for the gym. However this year I’ve bought a couple of packs of these which are a bit nicer.

Secret socks

Anyway back to pop socks. If I’m wearing trousers with a pair of shoes – and I don’t often in winter but if I do – then yes, on a cold day I wear pop socks, usually opaque ones. I just think they’re a more hygienic option under trousers than tights. Needless to say, Mr MC loathes them and truly believes that every other woman in the UK wears stockings and suspenders underneath her trousers. It’s a debate that’s been going on every single winter, ever since we met and it’s going nowhere but it’s probably another reason why I have so many ankle boots.

Before I go, just a couple of quick outfit shots that I found lurking on my camera roll. First of all in Manchester for a University Open Day a couple of weeks ago – lifting a basic black outfit with leopard boots.

best ankle boots for different trouser shapes

Jumper; Grandad shirt; Jeans (now in sale); Hush boots (gAW16), Portrait tote bag

And a sunny Saturday afternoon. I have a goal of acquiring every core wardrobe staple in my favourite pillarbox red and so I was feeling happy that I’d found a red blazer.

best ankle boots for different trouser shapes

Cord blazer (now in the sale); Breton (past season); Jeans; Shoes (gAW18); Mulberry bag (past season)

And with that I must crack back on with my day job because I’m horribly behind. I went down with a strange virus last week that just won’t go. It’s taken away my voice, my sense of smell and taste and even my hearing. I was croaking away to Mr MC on Saturday bemoaning the fact that it’s the second time I’ve been ill recently when he pointed out that in the last month, I’ve been to London twice, Manchester twice, Newcastle twice and Liverpool once. With the bereavement, two Awards Events and a business to keep running on top of the travel he suggested I may have been pushing myself a bit too hard. It’s funny how adrenalin keeps you going until your body suddenly takes over and forces you to slow down isn’t it? I’m not looking for sympathy, it’s just what women do but if you recognise yourself there, then take note. We’ve got Christmas ahead so we all need to be well. Take it easy this week because once bonfire night’s over, it’ll be full steam ahead with all that glitters!

Disclosure: ‘best ankle boots for different trouser shapes’ is not a sponsored post

Other Autumn/Winter 18 posts you may have missed

Amazing women over 50

Winter wardrobe building blocks

Chic new bags – the winter collection from Midlifechic

A week of two halves at Midlifechic

Coats knits and boots from JD Williams

Embracing autumn and bringing it in

Midlifechic edit – Marks & Spencer AW18

What I’ve been wearing and a midlife lately catch-up

John Lewis & Partners new women’s clothing review

Colour trends AW18 and how to work them

Key wearable trends AW18

How to wear Hush when you don’t do slouchy

Inès de La Fressange at Uniqlo AW18 review