If you've been walking around the streets of Sydney lately, you may have noticed the wide variety of ways men are "rolling their jeans." This trend is especially common among those sporting RM Williams boots. As a long-time fan of this iconic Australian footwear myself, I decided to dig a little deeper and find out what’s behind these different styles. Here’s what I discovered.
Why Roll Jeans in the First Place?
Rolling up your jeans isn’t just a random fashion quirk - it serves a purpose.
Balance your proportions: Rolling jeans can break up the flow from pant to shoe, especially if you have long legs.
Show off your footwear: A cuff or roll highlights your shoes or boots, adding an intentional style element to your outfit.
Add visual interest: When the inner lining of your jeans contrasts with the wash, a roll can make a polished, eye-catching statement.
How to Roll Up Jeans: Five Methods
Hemming
Hemming provides a permanent solution. A tailor can hem your jeans to avoid that dreaded “shredded jean back” look caused by dragging hems. Hemmed jeans are ideal if you want to keep things neat and avoid rolling altogether.
Who should hem?
Guys who want to look taller: Hemming keeps the leg line clean.
Guys who want to look slimmer: Hemmed jeans don’t add extra bulk.
Older men: Hemming is a conservative, no-fuss style that avoids the appearance of trying too hard.
Style Tip: Wear the shoes you plan to pair with your jeans when getting them hemmed for the perfect fit.
The Double Roll
A classic double roll is a simple and versatile look. Roll the hem twice, keeping each roll under an inch for a relaxed, nonchalant style. Avoid rolling more than twice - it can bulk up your legs unnecessarily.
Who should double roll?
All body types: The double roll adds just enough visual interest without overwhelming your proportions.
Younger men: This look adds a casual flair, but if you’ve hit your 40s, it might feel too youthful.
Style Tip: Aim for a 1.5-inch cuff and keep it slightly uneven to avoid a too-precise look.
The Pin Roll
The pin roll is for those who prefer a snug fit around the ankle. This method involves pinching the fabric at the inner seam and folding it before rolling the hem.
Who should pin roll?
Slim guys: Pin rolls look best with slim-cut jeans. If you’ve got bulkier legs, this style might feel restrictive or unflattering.
Style Tip: This roll works best with slim jeans and sneakers or casual boots.
The Deep Cuff
A deep cuff is a bold, fashion-forward look, often favored for showing off selvedge denim. The cuff is typically 3-4 inches tall but be aware that deep cuffs are derived from workwear styles, giving them a rugged, casual vibe.
Who should deep cuff?
Tall, slim men: Deep cuffs can break up the leg line, so shorter or stockier men should steer clear of this style.
Younger men: The deep cuff is great for a laid-back, casual look but may feel too sloppy for older men.
Style Tip: If you’re shorter but want that workwear vibe, go for a 2-inch roll instead of a deep cuff.
The Stack
‘Stacking’ refers to letting the excess fabric bunch up above your shoes. Popular in the music and streetwear industries, stacking works best with skinny jeans and high-ankle boots.
Who should stack?
Young guys: This trendy look is perfect for younger men who want a more laid-back, edgy vibe
Tall, thin men: Stacked jeans break up the leg line, so shorter men should avoid this style.
Style Tip: Make sure your jeans taper from the knee to the ankle. Otherwise, the stack will look unintentional and sloppy.
Bonus: When Not to Roll Your Jeans
Rolling jeans isn’t always appropriate. Here are a few times you should skip the roll altogether:
When the dress code is business casual or above.
When you want to look more mature.
When you want to look thinner.
Now that you know the differences between stacked, cuffed, and rolled jeans, and when to use each, you can confidently switch up your style to match any occasion. Whether you’re going for casual streetwear or a clean, classic look, you’ve got the tools to make sure your jeans are always on point. Who knew?
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