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I spent it all on clothes by the looks of things...

The Good Boot Guide

The alternative title could be ‘six styles of boots and what I might wear with them’, but that’s a bit wordy so we went with ‘the good boot guide’. Is it boot weather? I’m going to say yes, it is. Because it’s October, the month when attentions turn to coats, boots, knitwear and possibly some kind of pumpkin-flavoured hot beverage. Although I don’t mess with my coffee; give me a regular cappuccino with ‘normal’ milk, please. Even add a sugar and some chocolate on top while you’re at it. You can keep your pumpkin spice, your chai and your milk that doesn’t come from a cow, thank you very much.

I’ll get into knitwear and warm coat specifics another time, as today we’ll focus on boots. Which boots go with which outfits? As ever, that’s a matter of personal choice, but here are some ideas for you that I particularly like. I’m still on the fence about cowboy boots, but quite a few of you wanted some options, so I am here to serve…


As someone who usually shies away from any sort of heel, this kind of boot has been a revelation for me. I don’t know if the correct term is a ‘sock boot’, but I’m talking about a block-heeled, round-toed boot that is fitted at the ankle. I have two pairs, these from By Far and these from Sézane, and they are both VERY comfortable. I’m talking all-day comfortable too, not ‘in a taxi and out to sit down in a restaurant’ levels. I think the comfort directly relates to the width of the heel and the softness of the leather.

I am wearing mine with my wide-leg crops. Ideally, the trousers or jeans should fall to the top of the boots so that there’s no gap, so seek out boots that come to just above the ankle to get that look. I would also wear these with flared jeans and longer-length straight jeans or trousers. A good all-rounder for this season, I think.

sock boots and wide leg jeans

  1. Sea New York embroidered intarsia wool jumper
  2. Stradivarius soft wrap jacket 
  3. Polo Ralph Lauren wide leg crop jeans 
  4. Sezane Milo classic bag 
  5. Stuart Wiseman Sofia 50 leather ankle boots 
  6. Hush Tayla ankle boots 
  7. By Far heeled leather ankle boots (use code Kate15 for 15% off) 


OK, let’s get this one out of the way. I guess you could wear them with skinny jeans, but I think that’s a bit too ‘rodeo’. You could wear them under jeans but that’s giving Jimmy Nail circa ‘Crocodile Shoes’ vibes, or even Mick Dundee lost in New York. Not really the look we should be aiming for here. So I think I would go for an understated, short sweater dress or a simple shirt dress and let the boots do the talking. They might well be saying ‘take me off, you look ridiculous’, but ignore them.

  1. Phase Eight Candice puff sleeve mini dress 
  2. Inateannal cowboy hoop earrings 
  3. H&M knitted mini dress 
  4. Isabel Marant Oskan Moon leather shoulder bag 
  5. Gucci crystal embellished embroidered cowboy boots 
  6. ASRA Kaja leather western cowboy boots 
  7. M&S suede knee high cowboy boots 


These are the boots that never date. If you’ve had a pair of DMs since 1988, join the club. Although I wish I still had my original pair, then I wouldn’t have had to go through the whole rigmarole again of breaking those bastards in. My top tips are here. Once you have broken them in, though, they will last you forever. Or until you accidentally leave them in a cheap B&B in Edinburgh. Same goes for the Grenson Nanettes, but I didn’t have to break those in, and I haven’t lost a pair yet.

chunky boots and jeans

  1. Arket soft french terry sweatshirt 
  2. The North Face Cragmont fleece jacket 
  3. & Other Stories relaxed fit tapered jeans 
  4. Arket leather cross body bag 
  5. Grenson Nanette ginger nubuck boots
  6. AND/OR suede lace up utility boots 
  7. Dr Martens 1460 smooth leather lace up boots 


Now, I have a pair of these from Shoe the Bear, but I’m yet to debut them as I feel like they will work much better with tights than a bare leg, so I plan to pair them with a long skirt and a good blazer. When I was doing my last clear-out, I found this & Other Stories blazer that I thought I had lost two years ago. It was all scrunched up in the bottom of my son’s wardrobe. A quick steam and it’s now as good as new. I can’t advocate having a steamer enough. Especially good if you pack away your out-of-season clothes in vacuum-sealed bags. No more endless ironing, just a few minutes with a good steamer and your clothes are box fresh. I have this one, but I’m sure they’re all much of a muchness.

heeled ankle boots and maxi skirts

  1. M&S merino wool roll neck jumper 
  2. Monica Vinader Siren large gold hoop earrings (use code KATEH20MV for 20% off) 
  3. & Other Stories oversized blazer 
  4. Jigsaw crinkle bias cut maxi skirt 
  5. H&M black shoulder bag
  6. Shoe The Bear Paula suede ankle boots 
  7. Isabel Marant suede heeled ankle boots 
  8. John Lewis suede heeled ankle boots


Another classic. I’d imagine most of you have a pair of Chelsea boots in your wardrobe. If you don’t, then you might want to rectify that this year. Perfect worn with slightly cropped trousers, jeans and midi dresses or skirts. The timeless simplicity of these boots means they go with so many things and never go out of style.

  1. H&M grey marl knitted jumper 
  2. Astley Clarke gold played black onyx pendant necklace 
  3. Wyse London reversible puffer jacket 
  4. COS barrel leg wool trousers 
  5. Sezane Lena low leather boots 
  6. Dune dark tan leather Chelsea boots 
  7. Arket black leather Chelsea boots 


I feel like this is a look for grown-ups. You can, of course, wear your chunky or Chelsea boots with your dresses, but for a sleeker look, the knee-high boot is the one. Ideally, your dress should hang lower than the top of the boot – it will help make this outfit look more put together. I know we haven’t got into coats yet, but with a midi dress, you need your longest coat – one that will fall as close to the hem of your dress as possible so as not to cut you in half.

knee high boots and dresses

  1. Pink City Prints Chatsworth Gwen dress 
  2. John Lewis black jacquard animal print dress 
  3. Cefinn Eva merino wool knit maxi dress
  4. Dune Trinny knee high leather boots 
  5. Mango round toe leather knee high boots 
  6. Arket pointed kitten heel boots

I am going away this week so there is a chance I might not have time for full blog post next week, but I will do my best.

K x

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