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Six Autumn boot styles and how to wear them

Six autumn boots and how to wear them. A new pair of boots is a big purchase at this time of year. Styles come and go, but if you invest in a classic pair they should see you through for a very long while. I have Isabel Marant Dicker boots from 10 years ago that I still pull out every year because the style never changes and they still look good. Same goes for DM boots, classic black leather Chelsea boots and the Grenson Nanette hiker boots. If I’m to buy a new pair this year it will probably be knee-high boots. I don’t have any of those as yet so I’m considering if I would wear them enough to warrant a purchase.

Before you start your search, stop and have a little think about your personal style. What do you wear on a regular basis and what sort of boots would go with that? If you’re a bit confused about which boots work with which outfit, then I have some ideas for you. We will also look at trouser-leg length as I know that confuses a lot of people. Of course, there are no hard and fast rules – these are just some looks that I like.


Personally, I think the most useful of all boots is your quintessential, black leather Chelsea style. Not too chunky, not too dainty. They go with literally everything at this time of year, which is why they were an important addition to your 15-piece autumn capsule wardrobe a few weeks back. You can throw them on with jeans, dresses, trousers and skirts. For the sake of this blog I would team my Chelsea boots with a nice floral midi dress, just to butch it up a bit. Look for styles that are not too close-fitting at the top of the boot; this will be more flattering on the leg if you’re wearing with skirts and dresses.

1. Aligne relaxed fit floral maxi dress 

2. Tallulah & Hope Juliet green cord maxi dress 

3. Arket leather Chelsea boots 

4. Iris & Ink Claire leather Chelsea boots 


Similar to the Chelsea boot in their usefulness, but maybe more suited to those of you who tend to wear trousers more than skirts. Because lace-up boots can be tight at the ankle. As for the quandary about trouser-leg length, I think the best place for your hem to hit is about 1cm BELOW the top of your ankle boots. Too high and you get an annoying gap, too low and it doesn’t show your boots off enough and looks a bit dated. For jeans, the solution is easy – just roll the hem up or down as necessary. For trousers, look for ankle-length styles.

1. Maison Kitsune logo T shirt 

2. Hades Wool David Bowie jumper

3. Jigsaw Delmony washed black jeans 

4. Warehouse Ultimate button through liner jacket (use code WMM15 for extra 15% off) 

5. Geox Hoara leather lace up boots


If you’re thinking of buying into the ‘Western Boot’ trend this year, then may I respectfully suggest you go for an ankle boot version, ideally without tassels or any kind of embellishment. If you don’t heed this advice then I can almost guarantee you’ll be questioning your life choices come spring. Like when you go on holiday and decide to buy the local merchandise convinced you’ll wear it at home. You won’t wear that tie-dye, hand-weaved kaftan to the big Tescos, or ever again. You just got carried away in the moment. We’ve all been there. But if you go for a simple style like these or these, you’ll be able to wear them for years to come.

1. M&S faux shearling reversible textured jacket 

2. The Outnet BA&SH ruffle collar denim shirt 

3. Whistles Authentic slim leg jeans 

4. Isabel Marant suede Dicker boots 

5. Sezane Niels suede ankle boots 


If you’re a fan of leggings in the winter, or shorter, sweater-style dresses, then the flat, knee-high boot could be the one for you. Also good for those who can’t give up their skinny jeans, but note, they have to be REALLY skinny to work – nothing worse than trying to stuff trousers into boots only to have them all bunch up at the knees. We are not trying to look like Han Solo here, ladies.

1. Mango houndstooth check coat 

2. Carousel Jewels Gold hoops serpent earrings 

3. Whistles black funnel neck short jumper dress 

4. Shoe The Bear Pattie stretch leather knee boots 

5. Vagabond Eyra knee high boots 

6. Givenchy Antigona Sport small leather tote bag 


If you’re not a fan of your ankles and you want a pair of boots to give you a more slim-looking leg under your dresses, the heeled, knee-high boot could be your top choice. Whereas an ankle boot can break up the line of your legs, a heeled, knee-high boot will elongate everything. I love the look of an almond toe boot under a midi dress. They also work really well if you wear a lot of wide-leg trousers or jeans as they give the look that cool seventies vibe, and the addition of a heel stops your trousers from dragging in puddles. I like the look of these from Boden.

If you struggle to find knee boots to fit your calves, Erica Davies has a range for John Lewis launching on 11th Oct that could be your answer.

1. Pink City Prints Midnight Tiger Mumbai dress 

2. Warehouse relaxed fit double breasted coat 

3. Boden knee high leather boots 

4. John Lewis Sandie chocolate suede knee high boots 

5. La Redoute Calime suede knee high boots 


Finally your hiker-style boots. Should really have put these on last week’s ‘outdoors’ blog. If you can afford them, go for the original (and the best) Nanette boots from Grenson. For me, they come up true to size, but others prefer to go down a half size. I like room to wear my big, thick socks in the winter so do bear that in mind when buying this style of boot. For real ‘outdoors outdoors’ I also like the Sorel waterproof Kenetic hiker boots. I’d go up at least 1/2 a size in these.

1. Uniqlo lambswool ribbed round neck jumper

2. Acne Studios Valley check scarf 

3. H&M double breasted coat 

4. Hush Agnes straight leg jeans 

5. Grenson Nanette leather boots 

Next week we will take a look at winter coat styles. I followed the poll on my Instagram Stories. Although it was very tight at the top, boots just inched it over coats, but they are coming.

K x

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