I get many questions about the styles of shoes to pair with boyfriend jeans that are rolled at the hems. So here’s a guide that includes both dressy and casual footwear options. 

First, four important points: 

1. Low-contrast footwear, pointy toe footwear, and wearing heels will lengthen the leg line if you’re concerned about looking stumpy and dumpy in boyfriend jeans. 
2. Tucking or partially tucking the top will further lengthen the leg line and create structure. 
3. Cropped boyfriend jeans are proportionally easier to wear with flat shoes. 
4. Wearing a belt in the same colour as your shoes is an easy way to pull together the outfit. 

The examples that illustrate each style of footwear are by no means exhaustive. Think about the general style of the shoe as an option to wear with boyfriend jeans, as opposed to the specific style that is shown in the picture. Each footwear option comes in dark, light and patterned possibilities, and many variations. 

Also, think beyond hectically distressed boyfriend jeans if that’s not your look. Boyfriend jeans are available sans rips and holes. Lastly, find your sweet spot with respect to the height of the rolled cuff. Some footwear styles require a shorter roll than others.

Flat Booties

Choose chunky moto booties or flat Beatle booties. Cut-out booties with a one and half inch heel are another great option.

Heeled Booties 

Combining them with casual or dressy heeled booties is probably one of the most popular ways to wear boyfriend jeans. A great way to ground the look, lengthen the leg line, and stay warm. Wedge sneakers are another form of heeled bootie. 

Pointy Toe Pumps

The classic pointy toe pump is an elegant, refined and tailored option. Although pointy toe pumps with a stiletto heel are very trendy, feel free to wear round toes if that’s more your cup of tea. Pumps with lower and chunkier heels or wedge heels are another option. D‘Orsay pumps are another great look. 

Flat Sandals

Thong sandals and gladiators are an easy solution for casual days. The ultra breezy ped provides ventilation on a hot day when wearing jeans. 

Heeled Sandals

Heeled sandals are a dressier solution for hot days and still pretty breezy. Think all sorts of sandal styles, from casual wedged looks, to cage heels, extra high vamps, and ultra refined strappy styles. 

Peep-Toe Booties

Peep-toe booties and sandal booties are a trendy choice and fab in heeled or flat renditions. Suede styles tend to be extra comfy in this style of shoe. 

Loafers

With loafers making a fashionable comeback, why not wear them with boyfriend jeans. They’re a simpler version of flat oxfords and pretty chic. Round toe slipper flats are another style of loafer that looks great with boyfriend jeans. Boat shoes are great too. 

Pointy Toe Flats

Think ballet flats with pointy toes to extend the leg line. Round toe ballet flats are fine, but will create a slightly stumpier look. Wearing low-contrast round toes creates a less stumpy look. D’Orsay flats are another version of a pointy toe flat. 

Flat Oxfords

Flat oxfords are available with or without laces. I like to tuck the laces away so that the visual effect is more streamlined. A tomboy and arty option that’s pretty fun. 

Slip-On Sneakers 

Slip-on sneakers are another fab extra casual option. Choose soft leather or canvas. Orthotic inserts work well with this style. 

Birkenstock-esque Sandal

I’ll have more to say later about the fringe trending sandal that was inspired by the original Birkenstock, but in the meantime, it’s another very casual option for boyfriend jeans, and good for wide feet. It’s hip to be square, and some looks are frumpy right up until they are fashionable. 

Ankle Strap Pumps

The ankle strap pump is another refined, dressy and elegant solution, much like the pointy toe pump but with the addition of an ankle strap that is positioned above the ankle bone. Remember that you don’t need to have dainty ankles or long legs to sport ankle straps. 

Ankle Strap Flats 

Here’s a flat version of the ankle strap shoe that exposes the toes. Styles that cover the toes are just as fab. Make sure the ankle strap is positioned above the ankle bone and that the cuffs are rolled high enough to showcase the strap. 

I most enjoy wearing my boyfriend jeans with heeled and flat pointy toe booties, ankle strap pointy toe pumps, pointy toe pumps and heeled pointy toe oxfords. As soon as the weather warms up, I’ll be wearing them with ultra refined dressy flat loafers. I have worn my boyfriend jeans with slipper flats and flat oxfords, and am less fond of those pairings because they feel a little too boyish with my baggy and slouchy boyfriend jeans. I prefer pairing flat oxfords and slipper flats with tailored straight leg jeans. If I do end up getting slip-on sneakers, I’ll probably wear those with boyfriend jeans too.