Are you one of them?
Are you showing too much leg?
Picking a roll that makes you look short or fat?
Or one that looks weird with your boots?
Let’s teach you how to roll your jeans the right way.
Here are 5 methods of shortening your jeans – hemming, rolling, pin rolling, deep cuffs and stacking – and which boots they look best with.
Nothing lifts jeans from ‘scruffy boy’ to ‘stylish man’ like a pair of quality leather boots. Thursday Boots are a favorite of mine – born of the frustration that boots were either ugly and cheap or ridiculously expensive and delicate.
There are several benefits to rolling jeans.
– It breaks up the flow from pant to shoe – if you have really long legs this can balance out your proportion.
– It shows off more of your boot. You can keep the visual length of your legs intact while showing the details in a stylish pair of boots that otherwise would be covered up.
– It shows off the inside of your jeans. When the inner lining contrasts with the wash of your denim it can make a nice end point for the eyes to notice your boots. Or if you’re wearing high-end selvedge denim, you can make sure everyone knows about it. (Selvedge denim is woven on an old-fashioned shuttle loom, creating distinctive edges that only show on the ‘wrong’ side.)
#2. Avoid the tailor tax!
Don’t want to get every pair of jeans you own tailored? Rolling is a quick way to taper the cuffs without having to take them to the tailor.
Rolled hems can fall down at unexpected moments and get trampled on. I’m sure none of you deliberately buy floor-length jeans – but jeans stretch as you wear them and ride down as you walk, hems get wet and saggy in the rain, and before you know it you’ve trodden them into the sidewalk. Hem your jeans if you want to be sure to avoid the dreaded shredded jean back look.
When you take your jeans to the tailor, wear the kind of shoes you want to wear them with. Ask the tailor for ‘no break’ – i.e. hems that just rest on the tops of your shoes.
If you want to show off your shoes you can go higher, especially if you’re wearing chelsea style boots or high-top sneakers. Just be aware that the jeans will only be suitable for wearing those types of shoes.
Be wary of hemming brand-new jeans, because they can shrink when washed – especially raw denim, which is very in style at the moment. That’s denim that hasn’t been pre-washed. Unsanforized (non-shrink-proofed) raw denim can shrink by 5-10% , so you could end up showing 3 inches more leg than you meant to… suddenly not so stylish.
What Type Of Jeans To Hem:
Smarter jeans – although if they’re your first pair of nice jeans and/or you expect to get a lot of use out of them, you might want to avoid hemming to keep your options open.
Jeans with a wider leg opening – rolls, cuffs and stacks need some friction with your leg to stop them falling down.
What To Wear With Hemmed Jeans:
High-top footwear from sneakers to dress boots.
Smarter outfits like smart casual sport jackets and dress shoes go well with hemmed jeans, as it’s a cleaner look.
Who Should Wear Hemmed Jeans?
Guys who want to look taller – there’s nothing to break up the leg line, and if you cut them higher than the tops of your shoes you look slightly ‘too’ tall for your jeans… in a good way.
Guys who want to look thinner – hemmed jeans don’t add bulk to your legs.
Older men – hemmed jeans are a conservative style, so you won’t look like you’re trying too hard to be funky.
Rolling is what most guys mean when they say ‘cuffing your jeans’. A rolled hem is one that’s turned up twice. Never roll more than twice or you’ll look like you have bagels on your legs.
Aim for a 1.5″ cuff – the key is making the first roll less than an inch. Make each roll slightly lopsided for a nonchalant look.
Up until the 1960s cuffing your jeans was the norm, as they only came in a few lengths – so this is a retro look.
What Type Of Jeans To Roll:
Jeans that are full or half break length make for easy cuffs.
Selvedge denim that you want to show off.
Slim fitting jeans – the cuff needs some friction with your legs to stay up.
Designer jeans – most designer jeans come with very long inseams, and getting them hemmed will cost more than normal slacks and is something most tailors won’t attempt.
What To Wear With Rolled Jeans:
Pretty much anything that goes with jeans, but particularly:
Low-top sneakers or dress shoes – if you’re going to show some ankle the roll can look more balanced than the hemmed jean.
Motorcycle boots and a leather biker jacket.
Who Should Wear Rolled Jeans?
All body types can pull this look off pretty well, as it’s an ‘in between’ look that draws more attention to your ankles than hemming but less than stacks or deep cuffs.
Younger men – rolled jeans aren’t just for boys, but if you’ve hit 40 and are looking for a little more dignity in your style you should go for hemming.
#3. Pin Rolling
This is like a military shirt tuck for jean cuffs.
- Put on some un-cuffed jeans and stand up straight.
- Grab the inner seam at the bottom of one leg and pinch it.
- You will then want to fold the fabric against your ankle so the fabric now overlaps.
- You can now cuff the jean.
What Type Of Jeans To Pin Roll:
Slim fit – NOT classic or relaxed fit.
Jeans that taper at the ankle and are not too baggy above the knee.
What To Wear With Pin Rolled Jeans:
Chukka boots, combat boots, chelsea boots, laced boots.
Most casual clothing styles – this look is neither old-fashioned nor too trendy.
Who Should Wear Pin Rolled Jeans?
Guys who are slim enough to pull off slim-cut denim.
Deep cuffs are 3-4 inches tall. This might seem like the perfect way to show off your $200 selvedge denim jeans – but be aware that deep cuffs are derived from workwear, and still have a ‘working man’ vibe.
A deep cuff can have just one fold as opposed to two. (Smaller cuffs with only one fold will tend to fall down.)
What Type Of Jeans To Deep Cuff:
Slim fitting jeans – deep cuffs on baggy jeans will look clumsy and may fall down.
Rugged jeans – go with the workwear vibe.
What To Wear With Deep Cuffed Jeans:
Rugged casual looks like denim shirts, chore jackets, and watch caps.
Leather work boots or old-school high-top sneakers.
A casual work belt in tough matte leather. Work belts should be about 1.75 inches wide.
Who Should Wear Deep Cuffed Jeans?
Tall men – not recommended for shorter guys because they break up the leg line.
Slim men. Deep cuffs don’t flatter big or muscular guys.
Younger men – this is a more casual style and may look sloppy on older men.
‘Stacking’ means letting jeans fabric bunch up above your shoes. This used to be seen as lazy, but now the music industry has made it very fashion-forward. When you wear skinny jeans and high ankle boots there will be excess fabric around the ankle. Just let the excess fabric stack on top of itself and rock it! This only works if your jeans taper from the knee down to the ankle.
What Type Of Jeans To Stack:
Very slim to skinny jeans. I’m sorry – a stack still only works with uber-slim denim, so if that’s not your speed it’s best to leave this to those who embrace a pencil-thin leg.
Pre-washed jeans – raw denim is likely to rub indigo dye all over your shoes.
What To Wear With Stacked Jeans:
Urban casual looks like black leather jackets and hoodies. Stacks are a similar level of casual to deep cuffs but as urban as deep cuffs are country.
Running sneakers, Timberlands, rock star boots, cowboy boots.
Who Should Wear Stacked Jeans?
Guys in their 20s. This is a young fresh look on you. Enjoy your brief window of being able to pull it off.
Thin men. Given the need for skinny jeans, if you don’t have the legs of a newly born giraffe, steer clear.
Tall men. Like cuffs, stacks break up your leg line and make you look shorter.
Rolled and cuffed jeans draw attention to your footwear… how does yours look? Could you use a new pair of stylish men’s casual boots?
If so, click here to take a look at Thursday Boots – made with the highest quality materials available by skilled artisans, and you wouldn’t guess it from the price.