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

What To Wear With Your Hiking Boots

The short answer to What To Wear With Your Hiking Boots is whatever you damn well please, but that would be a very short post, so I will expand. I was going to call this post What To Get on With Your Grensons, but then I realised there are other brands out there, so I am trying to be impartial , but they are my favourites and I will sing the Grenson praises for a small minute. I just love the company, the story behind it, and of course the products.

Grenson has been around since 1866. All the shoes are still made and designed in the UK. They were originally a heritage Mens shoe brand, but launched a womenswear collection in 2008 and have gone from strength to strength. The Nanette boot is the one we all want, and I can vouch for the fact that they are super comfortable and go with pretty much everything in my wardrobe. I take my regular size, but some say they come up big and go down a half size. I get more questions about these boots than any other item of clothing I own!

The Original and best Grenson Nanette Boots

Of course, they are expensive, and I know not everyone has nearly £300 to drop on a pair of boots, so I have found some cheaper alternatives for you below. I’ve done my favourite outfits to wear with your hikers and as these are all outfits I wear regularly I didn’t have to rely on the usual search through Pinterest to find images to illustrate my point this time.

Apologies in advance for so much of my face, but it was easier to wade through my Instagram archive to show you the looks I’m talking about. Because of this, there’s also a fair few repeat items this week, all of which I own, so can vouch for them.


I love my red and black check jacket. It was from Set at Black White Denim. Unfortunately they don’t make it anymore. Anine Bing does similar, but I also just found this one from Next that is WAY cheaper. I can’t vouch for quality as I haven’t seen it in the flesh, but it looks like a great cheaper alternative.

Pair with your favorite slouchy (ideally cashmere because that’s the fabric of the gods) jumper and pair of Mom jeans from River Island. That’s another item of clothing that I get asked about all the time. They don’t sell the exact pair I bought earlier this year, but these ones are pretty damn close. They come up pretty spot on size-wise, but have no stretch, so go up a size if you don’t want to be sucked in too much by the high waist. Personally I love a suck-in high waist. The modern day equivalent of a corset.

1. Next Red Check Teddy Jacket 
2. Cos Cashmere Beanie Hat 
3. River Island Dark Blue High Rise Mom Jeans 
4. Hush Cashmere Boyfriend Jumper 
5. All Saint Fae Hiker Boots 


This is probably my favourite way to wear hikers. I think it’s a throwback to my 90’s grunge roots when all I wore were floral dresses and big boots. I was a suburban goth at school, then moved on to a bit of hair metal in my mid teens. In my late teens I discovered illegal raves and all that went along with them (sorry mum). In 1992 I moved to London and went to see the film Singles, the very next day I rushed out and bought Alice In Chains, Pearl Jam and The Lemonheads albums and a whole heap of flannel shirts and vintage dresses. Fickle? me? never… These days I’m less easily swayed by music related fashion trends, thank god, and I favour a good buffet dress with my boots.

1. Yas Greeta Long Sleeved Print Dress 
2. New Look Black Spot Tiered Dress
3. M&S Leather Hiking Boots 
4. New Look Faux Leather Hiking Boots 


Another of my classic go-to winter combos. I have tried to reign in my Fairisle obsession this year, but I did crumble and buy the Cashmere M&S on one of those 20% off Sparks weekends. The good people at M&S PR also kindly sent me the blue one below too. Both of them are great. One is over £100 and the other is less than £25. Remember those KIN jeans I’m always talking about, these Cords are basically the same shape, so they will be good ones. I would roll the hem up to show off my boots more.

1. M&S Fairisle Print Roll Neck Jumper 
2. APC Half Moon Leather Handbag 
3. Barbour National Trust Quilted Jacket 
4. Kin Cord Balloon Trousers 
5. Office Brown Leather Ansell Hiker Boots 


Are you getting the general idea now? Basically you could wear hiking boots with pretty much anything during the winter months. The only rule I have for you to to ignore men that ridicule you. That WILL happen as a lot of them still can’t get their heads around ladies not wearing dainty pretty shoes.

I have this entire outfit below. The skirt from M&S is nice and heavy and amazingly for a wrap skirt will not fly open to reveal your under-crackers at the smallest gust of wind. You do need to tie that side knot tight though. It has a tendency to come undone. The & Other Stories oversized blazer had been one of my best buys this season. I only bought it to qualify for free shipping when I got the Dinosaur cardi, but it never went back and I have worn it loads. I sized down one size as it is BIG.

1. & Other Stories Oversized Wool Blazer 
2. Kirstie Le Marque x Angie Smith Compass Necklace 
3. BWD Bella Freud Ginsberg Jumper (on sale) 
4. Per Una Satin Floral Print Wrap Skirt 
5. Grenson Nanette Hiking Style Boots 


If you’re after a more statement pair of hiking boots, why not go for a leopard print pair? (other animal prints are available but leopard is always king). I know I should be more adventurous with my print clashing, but I feel more comfortable sticking with plain block colours when I’m adding some leopard into the mix. Stripes are probably my only exception, but they are hardly a pattern are they?

I bought these Diemme boots last year as a birthday present to myself, but try as I might I could not break them in at all, they were just too small for me and gave me the worst blisters. Even my usually fail safe trick for breaking shoes in (anti blister hiking socks) didn’t help. with a heavy heart I gave up and sold them to someone with smaller feet, who I hope is enjoying them right now. This year I have an amazing pair of Shoe the Bear Agda Leopard print boots. Happy to report they needed no breaking in and are super comfortable.

1. Anine Bing Esme Sweatshirt 
2. Gucci Soho Disco Leather Bag 
3. Weekday Felicity Black Puffer Jacket 
4. H&M Slim High Black Ankle Jeans 
5. Grenson Nanette Leopard Prints Pony Hair Boots 

Have you bought into this trend? Do you have a pair of Grensons on Christmas list? I don’t have a Christmas list. I’ve made the fatal error of saying ‘Surprise me’. It can only end in tears.

K x

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