How To Find Your Perfect Boyfriend… Boyfriend Jean, That Is!

Ladies, we may not be a lot of help when it comes to finding the perfect boyfriend, but you know we’ve got your back when it comes to denim! And today, we’re sharing tips for finding and styling the perfect boyfriend jean.

We’re big fans of this laid-back look, but we also understand it can be a little intimidating to find the right fit. To find your perfect match, we recommend seeking out boyfriend styles from brands you’re already comfortable wearing. Start by trying on a few pairs in the same size you regularly wear in more traditional styles. This will give you a baseline, but don’t be afraid to go up or down a few sizes since each style is unique. You’ll be looking for a jean that sits low on the waist, has a slightly more relaxed upper fit than you’re used to, doesn’t hug your thighs too much, and isn’t too tight at the knee. The exact amount of slouch is up to you. Go with your gut and choose a fit that feels comfortable without looking too baggy.


If you just can’t fall in love with a true boyfriend jean, or if you’re looking for more variety, an alternative route is to go big in your favorite traditional styles. Depending on how relaxed you desire the jeans to look, we recommend going up two to three sizes and potentially even one fit (slim to regular, regular to curvy, or even slim to curvy). For example, if you typically wear a slim fit in a 28 inch waist, try out a regular fit in a size 30. Keep in mind that this strategy is all about experimenting. You will likely have several styles and sizes to determine the best fit for you.
The far left image shows the traditional fit of a Big Star Vintage slim jean, while the three pictures on the right show how a similar Big Star Vintage jean in a larger size and fit creates the illusion of a boyfriend look.

Once you’ve found a boyfriend jean you’re crazy about, the next move in this relationship is deciding what to pair it with. For a laid-back look, an over-sized tank or tee looks great tucked in at the front, paired with a belt and a casual shoe or short boot. If you’re aiming for a dressier feel, choose a fitted top layer and opt for heels or wedges. Either way, we recommend rolling the bottom of the jean to create a messy cuff. The truth is, this masculine style jean is surprisingly versatile and looks great even with more feminine pieces.

Whether your closest is already stocked with this look, or you’re looking to fall head over heels at first sight, we want to hear your questions and suggestions!