WearsMyMoney

As promised last week, herewith the BIG boot edit. We’re definitely entering boot season, so it’s best to get a foot in the door before all the good ones take a walk. OK, I promise that’ll be the end of the footwear-based wordplay for now. Otherwise, I’ll be here all day trying to think of more, and you’ll give me the boot…

Since everyone is looking for something different, I’ve rounded up a whopping eight styles to choose from today – with alternatives under each outfit, as always. There’s never really a right or wrong way to wear anything, but here are some outfits that I would personally pair with each boot style. So, let’s jump in with both feet (sorry).

 CHELSEA BOOTS & BARREL LEGS

Starting off strong with your classic Chelsea boots. They basically go with anything – all styles of trousers, long or short dresses, and most types of jeans – so if you’re after a good all-rounder, this is a great place to start. I’ve had a pair of the timeless Dr Martens Flora boots for years now, and they’re still going strong. They work particularly well with barrel jeans, as you need a boot that fits close to your ankle and slots nicely under the hem.

Speaking of jeans, I bought these ‘Twine’ jeans from COS the other week, and I can highly recommend. Even my husband commented that they were stylish, and so did the DPD man. Not sure which compliment I liked more.

1. Liberty Luv Lou Aviator Sunglasses
2. H&M Corduroy Jacket 
3. M&S Bouclé Fair Isle Crew Neck Jumper
4. COS Twine Barrel Leg Jeans 
5. Grenson Ingrid Leather Boots 
6. Demellier New York Midi Suede Tote bag 
7. Dr. Martens Flora Arcadia Leather Chelsea Boots
8. Russell & Bromley Dalton Leather Boots 

BIKER BOOTS AND FANCY SKIRTS

I have to admit, I had to think about this one. Short biker boots are having a bit of a resurgence this year. Back in the day, I would wear mine with skinny jeans, and that still works. But if you want a more 2025 take, I’d go with a lace or satin maxi skirt. These butch boots are a great way to de-girlify your cute skirts. Pair with a chunky rollneck for extra cool points.

1. Arket Roll-Neck Cashmere-Wool Jumper
2. Oliver Bonas Gold Pendant Cord Necklace
3. Stradivarius Oversize herringbone coat 
4. M&S Lace Pleated Midaxi Skirt
5. Coach Lana pebbled leather shoulder bag
6. Hobbs Kassandra Biker Boots 
7. & Other Stories Biker Boots

SUEDE BOOTS AND CROPPED CORDS

I have been coveting these Gucci boots since they came out maybe two years ago. There are some high-street homages available now, too: I think these from Russell & Bromley are probably the closest in style, but these M&S ones also look decent. They would work well with a nice pair of slightly cropped cord trousers (of which I have many), but also with shorter skirts as an alternative to loafers.

1. Uniqlo 100% Merino V Neck Jumper
2. Mint Velvet Triangle Knit Scarf
3. Astley Clarke Gold and Silver Hoop Earrings 
4. COS Checked Merino Wool Jacket 
5. Dehanche Hollyhock Suede Mixed Metal Belt
6. COS Cropped Cord Trousers 
7. Zara Ruched Split Suede Ankle Boots 
8. Gucci Horsebit Sylke suede boots
9. M&S Suede Chunky Block Heel Ankle Boots

FLAT KNEE HIGH BOOTS & MINI SKIRTS

I’m happy to say that the flat knee-high boot is also making a comeback, seeing as they sold out so quickly last year. My favourites back then were these COS riding boots, and they’ve brought them back this season. I managed to find a pair from Hush on Vinted last spring, so I’m actually set for the flat boots style now. I plan on wearing them with short skirts and 50 denier tights when it gets a bit colder. Again, if I’m wearing something a bit ladylike, I can’t help but want to butch it up a bit.

1. Charlotte Tilbury Red Lipstick
2. Rixo Merinda Merino Wool Cardigan
3. Hush Edie Pure Wool Double Faced Coat
4. Rixo Perla Knitted Top 
5. Arket Corduroy Wrap Skirt
6. Flattered Florentine Leather Black Boots
7. Schuh Dory Riding Style Boots

LACE UP BOOTS & TAPERED TROUSERS

Another classic boot style, but one that works better with trousers than skirts and dresses, I think. I’d wear a pair with tapered cords or turn-up jeans. They’re a bit too heavy and chunky to wear with wide-leg trousers.

1. New Look Argyle Knit Oversized Jumper
2. Uniqlo Double Breasted Long Coat
3. Toast Organic Cord barrel leg trousers 
4. Aleo Lola Ruse Suede Bag 
5. White Stuff Suede Hiker Cleated Walking Boots
6. Geox Serilda Lace-Up Ankle Boots
7. Grenson Corinne Leather Lace Ups

COWBOY BOOTS AND MIDI DRESSES

Long-time readers will know I bought a pair of cowboy boots when I went to Dallas two years ago. I tried to resist, but I got swept up in the location and the moment. Have I worn them here in the UK? No, I have not. But I will try. I think wearing them with a midi dress might be my best option. I went to a 21st birthday party a few weeks ago, and almost all the girls there were in cowboy boots. They wore them with short shorts or skin-tight mini dresses, and they looked wonderful – but I fear that’s a look best left to those who aren’t on HRT and don’t have to put their glasses on to read a menu.

1. Loel Small Gold Tassel Earrings
2. La Redoute Faux Suede Blazer Jacket
3. M&S Ditsy Floral Ruched Midaxi Dress
4. Isabel Marant studded leather shoulder bag
5. Paris Texas Hilda 35 suede cowboy boots
6. Zara Suede Cowboy Boots 

HEELED ANKLE BOOTS & WIDE LEG JEANS

If you’re looking for a specific boot style to wear with your wide-leg jeans or trousers, the heeled ankle boot is the one. Ideally, we’re looking for slim designs that fit close to the ankle, so they look chic and streamlined without the bulk. My favourite boots for wearing with my beloved patch-pocket jeans are the round-toe ‘sock’ style, like these from Air & Grace.

1. ME +EM Silk Blouse and Tie 
2. Whistles Black Single Breasted Blazer 
3. Reiss Patch-Pocket Flared Jeans
4. & Other Stories Leather-Trimmed Suede Tote Bag
5. Casetify Custom Phone Case 
6. Air & Grace Black Leather Ankle Boots
7. & Other Stories Sock Boots 

HEELED KNEE HIGH BOOTS & MIDI SKIRT

Finally, another popular choice is the sleek, heeled knee-high boot. These will immediately make you look more ladylike and elegant. I feel like proper grown-up ladies wear this style. They’re perfect paired with an understated midi skirt or dress. Combined with the heel, the length of these boots really elongates even the shortest of legs.

1. Wardrobe 44 Alex Cardigan 
2. Monica Vinader Siren Muse Huggie Earrings
3. Zara soft oversized coat 
4. Monsoon Lana Suedette Midi Skirt
5. Liffner Mega Sprout Suede Tote 
6. Boden Skye Smart Knee Boots
7. Sezane Garrett Knee Boots 

I hope this helps you find your perfect pair. If you’re looking for a autumn jacket to go with, see this post and I will do coats in a few weeks — they haven’t all come in yet so we need to be patient.

K x