What Shoes to Wear With 6 Popular Jean Styles: My Go-To Pairings

I get a lot of messages about what kinds of shoes and boots go with which jeans and trousers. As with anything style-related, there are no hard and fast rules for this. You are (as ever) free to wear whatever you want, whenever you want. Some exceptions apply (no bikini tops in the workplace unless you’re a lifeguard would be one), but a lot of us have reached an age where, frankly, we don’t give much of a shit about rules.

But, as this is my blog, these are my opinions. You are welcome to listen to them and take them on board if you feel so inclined. This week, I’ve also included examples of me wearing these jeans-and-shoes combinations. I don’t have any formal styling training, but I know what I like and I have been sharing that here for almost 10 YEARS! How time flies. Shout-out to anyone who has been here since 2016. You are the true OGs.

It’s also my birthday today. I am 53. There was a time when that was considered really bloody old. Mrs Slocombe in Are You Being Served was only 46 when that show started. How times have changed.

Let’s get on with the jeans and the shoes – for all of us who don’t feel our age.

WIDE LEG JEANS AND CLASSIC LOAFERS

This is my current favourite jeans-and-shoes combo. It works with most styles of denim, to be honest – but particularly well with a nice wide-leg pair. Wide-leg jeans can look a bit odd with a chunky shoe, so stick with a classic, slim-style loafer here. Neat flats or heeled boots also work well.

BARREL LEG JEANS AND SLIM BOOTS

I actually think barrel-leg jeans can work with a whole lot of different boot styles. The only real thing to consider is the length of your jeans in relation to the top of your boots. Ideally, for me, the hem of the jeans should hit the top of the boots. I don’t really like full-length barrel jeans; I think they look best when they sit on the ankle. These from M&S work perfectly for me on that front. I’m 5’7 (or 5’6, according to the doctor, but I’m not having that), and I wear them in the regular length.

STRAIGHT FIT JEANS & FLATS

Maybe not the most practical footwear in the current inclement weather, but if you’re a fan of a ballet flat, they work very well with a classic straight-leg or loose-fit pair of jeans. Slimline trainers, like my favourite Adidas Spezials, also go well with this look. Side bar; I’m sure I’m the last person to be converted to this Victoria Beckham eyeliner, it’s so good. It glides on like no other I’ve tried and very easy to smudge around, plus it last all day. I’m a convert.

LOOSE CROPPED JEANS & CHUNKY LOAFERS

For me, anything chunky on the feet should be balanced out with a loose-fit pair of trousers or jeans. This can be loafers, boots or trainers. I like a slightly cropped style here too; otherwise, it can feel too bulky around the ankle. Plus, this is a good way of showing off your nice socks. These jeans from COS are super soft and a bit oversized. I got my usual size but I do have to wear a belt with them.

BAGGY JEANS & TRAINERS

A neat pair of trainers is my go-to when wearing baggier, full-length jeans. These from Air & Grace are ideal, as they’re slightly smarter than your usual trainers. We want to avoid looking like a teenage boy in our baggy jeans.

CROPPED STRAIGHT JEANS & CHELSEA BOOTS

These can work with any pair of cropped jeans or trousers. Again, I don’t like them so much with full-length styles. I think Chelsea boots are made to have the ankle part showing. This is actually a great look if you suffer from ‘cankles’, as Chelsea-style boots should fit close to your ankles, which gives you more shape in that area.

I hope this has been somewhat helpful. All these ideas can also be applied to trousers if you’re not a jeans fan. But if you’re not a jeans fan, what are you doing here in the first place?

K x

WearsMyMoney

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