Introduction
Yes that’s right, boots are back! For the past year now, I have noticed boots slowly creeping their way back into many ‘a man’s wardrobe. I begin to ask myself what is it we love about these blister creating, ankle-busting brutes? The origins are normally associated with old-school punks or were to be found on the shelves of VW (Westwood, not the car). All of that aside, paired with a decent pair of jeans just about anyone can rock a look to boot.
A decent pair of boots does not have to cost an arm and a leg. Many high-street retailers and online fashion stores are stocking up on these winter essentials. A small investment now will see you as far as future fashions have been predicted.
Right boot forward
Choosing the right pair of boots to go with your outfit is essential. One false move can result in code red on the fashion scale; red is not the pantone colour of this outfit scale! Here are my three most popular boot styles with a few ideas to help you on the way to picking that perfect pair:
Calf high boots
Calf high military boots are bang on trend this season. Find a pair complete with some creasing and scuff marks, which creates that perfect worn “I don’t really give a damn look” before your feet have even grazed their in-souls.
These boots look good with skinny/slim jeans tucked into or if you fancy being a bit more daring with your clothing, a pair of cream chinos tucked into the boot with some brown socks just peeping out of the top. This is a popular look I’ve been seeing a lot of this season (town meets country) but remember to vary the colour of your trousers and socks accordingly.
Ankle boots
Boots don’t have to be strictly limited to casual daywear. Ankle boots prove that fashion forward footwear can be used for both work and play. This particular style would work great to dress down a suit; so lose the tie, unbutton a few buttons on your shirt (or sub in a plain tee) and go straight from the office to the bar. For a daytime look you can team them up with a pair of black skinny jeans and a statement t-shirt to create a fierce look sure to turn heads, but for all the right reasons.
Brogued Boots
A transferable look can be achieved with these sorts, all it takes it imagination. Brogued boots look great with blue washed jeans tucked in to for a daytime look. If you want to impress your boss, wear them with some grey trousers and you’ll be sure to get a promotion in the style ranks. Brown brogues of any cut play to this season’s earthy colour scheme.
Boot Looks

How to style
The trick is to make your outfit look effortless. Wearing skinny jeans tucked into boots will create a clean, vertical sweep down the leg. Alternatively, if you prefer slightly looser fitting jeans, then do not leave a bundle of fabric gathered above the boot, a small amount is acceptable but don’t push it! This will create an unsightly clash enough to make anyone’s eyes bleed.
With the more ‘rustic’ style boots you can partner staple accessories around them such as gloves, hats and bags to create the key A/W nomad trend.
I am wise to the temptation after spending an hour getting ready to then find out you have no shoes to match that perfect outfit. You misguidedly just stick anything on your feet; this is a BAD CHOICE. Your footwear is one of the first things that people notice about your look.
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I’m with you on the part which you state “footwear is one of the first things people notice” It really is.
I see you’ve got the Temple & March boots from topman featured there, these are such a key trend and best sellers for topman lately and the amount of people who are buying these to use with carrot fit jeans, is amazing.
Boots this year is already a massive trend and I can see it sticking for some time.
One extra thing though is the High Temple 2 boots at topman – These are my best sellers for the past two weeks, allowing the boots to “fold” over so they are roughly the same hight as the ones featured but giving more texture and display to the carrot jeans.
Do boots work on shorter guys, or do they just make us look shorter?
To COFFEEPAPERTREND – Actually wearing boots with a skinny jean tucked into them will elongate the leg and make you look taller. The one thing I would suggest not to do is wearing baggy worker jeans tucked into boots, as this will make your legs appear a little on the plump side and make you look shorter.
To MATHEW – Thank you for your agreement on the matter, and that is the style I have seen most of this year. And I do believe I may have just purchased those boots myself come to mention it.
I love the christian Peau boots at the bottom, just ordered a pair now :)
Brilliant article ! your pictures show so many styles, but i just dont know which ones are best for my large calfs/ankles = cankles as they are a weight bearing joint and i have alot of that ahaa, weight that is :P Sometimes i feel like my feet are made of iron.they support the rest of my fatty tissue and i want to treat them right. The synaptic fluid sometimes builds up around my ligaments/tendons causing inflamation to my cankle. Any ideas? Write back soon blisters are developing as we speak.com
totalaccident.com
What Matt said, I’m 5’10 and wearing skinny jeans tucked into boots makes me look and feel taller! I tried some drop crotch and baggy jeans and they definitely make you appear shorter and fatter lol. They don’t have to be super skinny, a slim fitting straight leg looks fine also. I tend to go for Nudie Thin Finn’s which are in between a skinny and straight leg. I’m glad boots are here to stay, I don’t know how I survived before them:)
I’ve got some military boots (buckle / charcoal / leather detail) and I’m wearing SLIM jeans. For me, tucking jeans is a step too far and my legs seem to disappear (I’m about 6 foot but my height seems to be in my upper body). But I do want to show off the boots. So I’ve been rolling the jeans up a few inches to get the best of both worlds. Is this fine or do you reckon it should be all or nothing??
I think you should go with what you personally think suits your body. The point I made was just a general rule of thumb, but sadly the look won’t work for everybody. If you feel more comfortable with your jeans rolled up then that’s the look you should stick with :)
hey matt, i can just see you replied to everyone else but me, do you think im some sort or joke? the situation is getting outta control right here, my cankles have swelled up to 8 times the size, any help hereeee? they are beginning to feel the chaffing from dragging on the snow. dey are cold. lol:P brrrrrrr.co.uk/coldness=pain
@Josh – No-one thinks you are a joke mate, sometimes comments are missed when there are a few. The problems you are describing above seem to be more physiological problems, in which case unfortunately the only way of telling what works for YOUR body type is by you trying on several pairs and experimenting with different footwear styles.
Personally if I had to make an educated guess, I would say to go for a military boot which should provide strong and structured support for your feet and bottom half of your leg, but look to buy those that do not lace up all the way to the top as I am sure you would find this constrictive. Look to go for a pair where you can choose to lace them up at the top of the boot or leave them undone in order to give your lower leg more room to breath and hopefully not swell up. Some are shown above
http://www.stand-out.net/Murdoch-Military-Boots-pr-5571.html
Like I say though, you own personal experimentation is the key to solving this particular problem. Styling issues we can give you much better advice ;)
Mid calf boots are my new favourite for winter footwear (I previously kept to ankle boots, but decided it was time to try something new this year). I have a pair of distressed military style boots from River Island, and they work great with my leather-look jacket or to dress down my wool pea-coat. Being leather they’re not half bad at keeping feet warm too.
Though I’m starting to see more guys wear boots, they’re almost exclusively ankle height. Not sure if some guys consider anything higher to be too feminine, or they’re worried about the ‘fascist boot’ jokes (my brother plays that card even with my ankle height ones, lol), but if done well (and it’s actually easier than you might think; great tips in this article by the way) calf height boots add a lot of statement to an outfit.
Hi there! great article..Just a quick question, where can i get those tan brogues that’s in the top picture (the middle pair)? Thanks
To PAUL B: I couldn’t agree more. Personally I adore my calf high boots, and have treated myself to several pairs this winter (i’m sure my family won’t mind not recieving any christmas presents for just one year) and as well as looking great, they keep the snow out!
To MTC: The picture of the brogues was just a general picture from a website, but I i’ve managed to track down a pair online that best match the ones in the image. Here is the link to the website, hope you find what you’re looking for: http://www.my-wardrobe.com/loake/tan-burtford-brogued-country-boots-684930
Thanks for the link Matthew…Great stuff! MTC
What’s your opinion on military boots from military surplus stores and recommendations on military style boots for uk size 13?
Great article Matthew. I have a pair of distressed All Saints Military boots. Do you know the best way to care for them? Usually I would polish boots to build up a protective skin but I assume that will ruin the distressed look of these.
Thanks in advance.
To Neil D: Military boots from military stores tend to be more practical than fashionable. If you like the appearance of the boots then that’s great because they are still part of the military trend, however I wouldn’t hold out for anything too spectacular. Also, if you have quite long feet and slim legs, then wearing skinny jeans is a no no i’m afraid as this will make you look like you have clown feet. I would recommend wearing the boots quite loosely around the top and perhaps slightly tucking some worker jeans into them. Hope this was helpful and thank you for your comment :)
To ElectroRoss: I’m no expert on the matter, but I do believe you can buy distressed leather conditioners, which are obviously tailor made to clean boots like yours. Here is a link to a website which sells the product, and it is also relatively cheap at $5.00. Hope you find what you are looking for http://shop.fiebing.com/products/category/3267.0.75170.72705.72744.0.0
Thanks Matthew