Following on from one of my previous articles, I wanted to address one of the issues brought up but some of our readers, namely what footwear to pair with skinny jeans. This is an issue I can fully understand, as a strong advocate of the skinny jeans wearing fraternity, the problems of suitable footwear are only too clear. However, the good news is that, with the quite frankly vast selection of styles, shapes, colours and sizes available, there is almost certainly the right pair of shoes for you.

Now, if we’re tackling the question of what shoes to wear with skinny jeans, it’s probably worth identifying the specific issues that arise. One of the main problems and one which I seem to hear a lot is that because of the very slim and tapered shape of the leg, many types of shoe tend to look somewhat clown–like, therefore necessitating the need for slim or thinner shoes. But this is not always the case, as I shall explain later. Another problem raised was ‘stacking’, whereby the jeans, rather than break over the shoe, gather at the top, creating folds of material, resulting in jeans that look ill fitting and scruffy.

With regards to this second problem, I have found that the choice of shoe is only half the problem; ‘stacking’ is also caused by the jeans themselves. Because the fit and cut of jeans (even when pigeon holed into a specific style) can vary so much between the different brands and retailers, you may find it hard to find the perfect fit and style for your individual tastes. At this point we must consider the two different and most common ways of buying skinny jeans. Obviously one is to buy the jeans made for men, the other (and here is what causes a lot of controversy) is to buy women’s skinny jeans. But why is this important? Well, there is quite a marked difference between the cut of men and women’s jeans, while the male versions tend to taper but still keep a wider cuff around the ankle, the female designs taper to a much more severe point and generally stay much tighter to the leg, they also tend to be a bit shorter in length stopping at the top of the shoe, where as men’s jeans are longer and because of this more relaxed fit around the ankle, have more material to bunch up or ‘Stack’.

Now that is not to say that we should all rush out and buy women’s skinny jeans to solve our problem, far from it. I know from personal experience that women’s jeans do not always work on men, because we have a different build – its just nature and anyway I know I’d feel rather self conscious browsing the women’s jeans section. Unfortunately the answer isn’t as simple as buying slightly shorter legs than normal, because this alters the whole shape of the leg, making them much tighter all the way up. The solution to this half of the problem is do some market research and be prepared to pay a little bit more for the perfect pair of jeans. I’m all for fashion for less but sometimes paying that extra £10 makes a big difference.

My personal choice are Cheap Monday jeans, they are cut more like women’s jeans; tighter round the ankle, and a bit shorter so they don’t stack, but most importantly for me, they still crease at the knee – a key feature – which I think marks out a clear difference between male and female skinny jeans. If the jeans are right then there shouldn’t be as much of an issue with ‘stacking’. However you do have to accept that with men’s jeans there will always be an element of it with nearly all your footwear, because you cannot of course expect a tighter ankle to break neatly over the top of EVERY shoe, it just can’t and if your wearing hi-tops or boots your taking the shoe to the jeans, so it is somewhat inevitable. I also think, in a similar way to the crease at the knee, that ‘stacking’ helps to maintain a more masculine image (again one of the many debatable aspects of skinny jeans) because it doesn’t taper to such a point – a feature of the fairer gender skinny jeans.

Personally, I believe this issue of clown feet and skinny jeans is something of a myth. Certainly from a fashion point of view, larger shoes create a clash of styles and shapes – a key part of fashion experimentation – of course, this is still a matter of personal opinion, what I think looks good isn’t necessarily what you think, and if you just have large feet in proportion to your body, then you might find them a little at odds with the whole look. In general though, I think you could wear almost any style of shoe you want, from flip flop to Doc Martins.

Before I get to into the different types of footwear you could use, I thought it would be a good idea to show you my personal choices. These are the actual shoes I wear most of the time, you just have to imagine them a bit more used (my Hi-tops haven’t been this white for many a month).

Footwear For Skinny Jeans
The Brogue

The Brogue is one of the great British institutions, originating from Scotland and Ireland as a rudimentary walking shoe. It must therefore be treated with respect. For the current A/W trends they are perfect, fitting right into the heritage, town meets country and urban bohemia trends.

Use them for formal occasions or dress them down for a night out. I find brogue boots tend to work better with skinny jeans because the extra height can be covered by the jeans making for much smoother lines, rather than there being an abrupt divide between jean and shoe. They also make a fine alternative to military boots should you want to go really bohemian and wear them with the jeans tucked in. However you wish to wear them, remember to keep your outfit smarter and think tailoring.

The Pointy Shoe

Apologies for any lack of clarity in the sub heading, but you get what I mean. Sadly this style has become somewhat clichéd nowadays. Too many Indie musicians, Noel Fieldings and Russell Brands have almost spoiled this delicious broth. All is not lost however, Chelsea boots still remain a very fashionable choice and go great with skinny jeans.

Again I’m not a huge fan of just standard pointed shoes, as with brogues the abrupt division between shoe and jean doesn’t work for me, and they have become a little to common for my liking, there is very little individuality. Similarly to brogues, use tailored or more formal items, cardigans, shirts, polos, blazers etc. Both styles are great for creating a Mod vibe within your outfit (which I’m hugely fond of) and when worn correctly, look brilliant.


Perhaps a more summery footwear style here, best teamed with rolled up skinny chinos or jeans, without socks and with a crisp shirt or polo buttoned up to the top for a quintessential Mod inspired look. As this is winter however, you’d best roll those trousers down and crack out the thick socks. The best thing about loafers is their versatility, as explained by Ben Herbert in his article on Tasselled Loafers. They can be used within almost any outfit, being able to dress up and dress down, or add a little individuality to a tux or dinner suit. To get the most out of them, go for brown/tan or black leather.

One thing I would like to stress at this point and then pound into the heads of the fashionable, leather shoe wearing male population of Britain is that you should ALWAYS POLISH YOUR SHOES. The number of people who wear leather shoes, (particularly the younger generation) and don’t perform this simple task is simply infuriating. Not only do your shoes last longer and feel nicer but they look better. People will always notice your shoes; they are a very important part of an outfit and should therefore be treated well. If you, like me, have made a significant investment in your shoes (which I suggest you do, quality shoes are just better you want them to last as long as possible and look as good as possible.

Military boots

With military style boots you are embracing a far more relaxed and informal look, although you could still mix them into a formal outfit. Replacing your shoes with boots, tucking in your trousers whilst keeping the shirt and blazer but loosing the tie, creates a nice contrast without being too brash and obvious.

As with Brogues, military boots suit the current A/W trends perfectly, team them with your heritage pieces, chunky knits and woolly accessories to make a great winter statement and stay toasty war at the same time. To cap it all off most styles are also fairly slim lined, so you avoid the possibility of your feet looking oversized or clown like.

Boat Shoes

Another massive S/S trend this year, reviving and reinventing a style mostly confined to the yacht club and landed gentry. Perhaps more suited to summer usage than in the colder months, they still provide a great casual alternative to plimsolls or lo tops.

If you’re feeling brave, roll up your skinny jeans (or chinos for that matter) and forgo the restrictive socks, just make sure you layer everywhere else, no sense in all of your body getting cold in the name of fashion. If that’s not your cup of tea then keep them rolled down and you can use them with almost any style you care to think of. As with all the styles here, they fit the A/W trends brilliantly.

Hi Tops

Obviously, smarter footwear is not the only style you can use with skinny jeans. Hi tops have come back in a big way in the last couple of seasons and they are a great way to inject a bit of colour and individuality into an outfit. Because of their size and tendency to be made in very vibrant colours they immediately become the focal point of any look, made all the more evident because of the clash between slim legs and chunky feet.

What you have to decide is how chunky and loud you want them to be – would you like to create a contrast of styles or retain a pretty slim lined look all the way through? Generally the offerings from Adidas and Nike are fairly substantial and use bright colours, a clear influence of the basketball background. While Puma and the smaller brands tend to use slimmer lines and more subtle colours (I also own the green and white pair from Puma shown below).

Whatever style you go for, try not to do them all the way up and push your jeans down inside the shoe, this helps with the stacking problem and helps retain the skinny profile of the jeans. Use them in your casual outfits or use with more tailored items such as blazers and cardigans for a more sophisticated and fun look.

Lo Tops

Here we have a good footwear choice for those new to the world of skinny jeans. Low profile trainers offer the casual, everyday element of informal shoes as well as the ability to be dressed up for a night out. I would suggest sticking to very simple, clean styles in basic colours, because they will be the most transitional, offering you complete versatility and a way of easily incorporating them into almost any outfit. You can of course use them to add some colour to an outfit, in which case Adidas superstars offer a classic style with a lot of colour variation.

Final Word

I wish to make it clear now that this is certainly not a comprehensive and exhaustive list. As I mentioned earlier, you can wear almost any style of shoe you like with skinny jeans, you just have to tailor your choice to the overall style you are trying to achieve. You can of course, wear Espadrilles, Chukka/Desert Boots, plimsolls (although I would avoid these to steer clear of any clichés) or flip flops. Just remember, the correct selection of jeans will make a big difference to how good or bad a shoe looks. Spend a little bit more money and time on getting the right pair of jeans and the shoes should follow.

  • Do you all agree, or am I talking a load of Rubbish?
  • Who are your favourite makers of skinny jeans and what price do they come in?
  • Are there any other styles you think can be used with Skinny jeans?
  • What is your favourite type of footwear to pair with your skinnies?

Let me know in the comments below.