Boyfriend jeans offer a roomy alternative to skinnies and jeggings, and are an extremely comfortable, ultra-relaxed denim option. The tomboy vibe they create is fun, modern and on-trend. There have been many, many questions about the fit and styling options of boyfriend jeans on our forum lately, so I thought I would outline the way I break down the decision of which pair to purchase and how to wear them. 

1. Find your Bagginess

The photos show an assortment of boyfriend jeans with varying degrees of bagginess. Some styles are slim fitting and are virtually cropped skinnies (the first two pairs). Others are roomier on the hips and thighs, but fitted on the waist, bottom and tummy. And some styles are unstructured and roomy enough for the crotch point to drop (the last 3 pairs). In fact, they slide right off, even when the button and zipper is fastened, and wearing a belt is the only way to keep them up. 

If figure flattery is your top priority and you prefer to wear tailored clothing, slim style, structured boyfriend jeans are best. If you really want to embrace the authentic boyfriend jeans trend and are happy to forego a little figure flattery, go super baggy. The good news is that there is also an option in-between that allows you to bat a bit for both teams. In this case the slightly all over baggy fit that is still structured is the way to go.

My own sweet spot is pretty baggy. I sized up on my Sexy Gap boyfriend jeans (which I call my “Husband Jeans”) in order to achieve the same baggy fit that’s on the model. The crotch point is dropped and they fall right off without a belt. They are roomy on the thigh, bottom and tummy area. The fabric bunches on the waistline when I add a hip slung belt. But this is how I want them to fit because it’s the look that I’m going for. A less baggy pair of boyfriend jeans was more figure flattering, but the baggier style stole my heart because they are fun to wear and look more “tomboy”. Remember that you sometimes forego a little conventional figure flattery in order to create an edgier look. 

2. Find your Waistline

Most boyfriend jeans have mid length rises. A fitted pair will keep the same position of the waistband with and without a belt and tucked top. But an extra baggy pair of boyfriend jeans, because you’re swimming in the style, allows you to manipulate the position of the waistline by wearing a belt. Wear the belt tight with a tucked top, and you’ll create a higher rise and more natural waistline. Wear the belt loose so that the crotch point of the jeans drops, and the waistline is low rise. 

Since my boyfriend jeans are baggy and loose, I only wear them with a belt and fully tucked top because it gives the look more structure and polish. This is by no means a rule, but it is the way the silhouette works best for my style. Semi tucking a top works particularly well for boyfriend jeans too. 

3. Find Your Length 

Sort out the length after finding your waistline because the position on your waist will affect the length on your leg. Roll up the hem to the length that you prefer. I like the variations around calf length that are shown below, some a little shorter and some a little longer. To my eye, they flatter the length of the leg line. I do not find the “just above the ankle” lengths flattering unless the hems are very tapered (as they are in the first pair in row 2 below). You might need to taper the hems of the jeans a little more to get the desired effect, and that’s an easy alteration. 

At 5 ft 6, I wear my boyfriend jeans rolled up five inches above my ankle bone, both with flats and low heels. They are too short to wear full length, but they’ll work with mid calf and taller ankle booties. 

4. Find Your Wash 

As with all denim, choose your degree of distress. Boyfriend jeans are typically quite faded and distressed, but darker washed are available too. 

Feel free to ask further questions in the comments section. Do you wear boyfriend jeans? If so, what’s your baggy sweet spot, and how do you like to style them? Or are boyfriend jeans not your thing.