How to Style Vintage Jeans

Vintage jeans are gold to fashionistas and denim collectors, with big money being offered on internet auction sites for rare examples. Case in point – a rare pair of 1950s anniversary Levi Jeans were listed for $8,000 only three years ago. The sad reality is that there are some people who could wear these jeans and look fantastic, while others could don them and look terrible – purely because of the items that are accompanying them.



To name but a few for women: Ultra high-waisted. Dark skinny, light skinny. Frayed edge. Wide leg. Cropped. Men’s jeans examples include skinny, officer, copperfill loose and corporal.

Poorly styled jeans look dreadful, but surveys have found that up to 40% of women struggle to find the perfect fit, so they may plump for ones which are less perfect or which are ‘in’ this season. Ideally, your body shape should dictate the jeans you go for. The tall skinny physique can look good in virtually any shape of jeans, while the apple shape should opt for stretching elasticated waists, while a pear shape (small top half) should go for high waist.

Conversely, long legs and high waist aren’t often preferable, and they should instead go for low or mid-waists.

For men, only really consider ‘spray-on’ jeans if you are well-proportioned and well-maintained. Such jeans on small legs will make those legs just appear smaller, while tall and skinny frames will only appear taller and skinnier. The purpose of skinny jeans is to flatter the physique, rather than pinpoint perceived weaknesses.

Then there’s the choice of wash; simply put, which do you like? The lighter, 90s-style blue, or a deeper, starker indigo, that appear harder-wearing and tougher. Jeans fade as you wash them (or if you choose to) which might be taken into account, eventually turning black to a charcoal colour.


Here’s the problem; the wearers of jeans are often embarrassed by the size that would suit them best. Wearers of both sexes don’t want to have a 38-inch waist, so they try to squeeze themselves into something that they think ‘should’ fit them. Sizes have changed over the decades and there’s no guarantee that you’ll fit in a size 14 from 30 years ago, even if you fit in a 14 now.


Vintage jeans are not just a fashion item, but also an investment. With that in mind, even if you never get to wear them it’s worth knowing what adds value to a pair. Dark is worth more than faded, a ‘Big E’ on the tab is worth more than a ‘Little e’, and certain sizes are worth more than others.


Assuming that you’ve gone for the more traditional look as opposed to the brightly-coloured abominations of Russell Brand et al, then most of what you choose to wear on your top should be OK. There are a huge number of various looks to slim yourself such as these for women, while this piece shows the various things men could wear alongside jeans such as a moto jacket or a military-style blazer. You may wish to pair them with another piece of vintage clothing such as these Pinterest efforts, which include some fabulous double denim. If all else fails, go for the simple plain t-shirt; unfussy, tidy, simple and smart.