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. 

Here are two pairs of on trend shoes that are comfortable and fab for Spring and Summer. 

• Sam Edelman Ollie T-Strap Pump: Similar to Valentino’s Rockstud triple ankle strap pump at a fraction of the price. Personally, I find the Ollie’s more comfortable than the Valentinos, but they are obviously not as refined and beautifully made. If you find the Okalas comfortable, these are a similar fit. 
• Carvela Kurt Geiger Agnes Bootie: Refined cut-out booties with pointy toes that are super comfy are hard to find, but these fit the bill. Unfortunately, the photo does not do them justice. They look more hip in person. 

The cut-out booties look great on bare legs and with hosiery. The built-up sole allows the addition of an orthotic. The Ollie pumps are best on bare legs. Think skirts, dresses, long shorts, boyfriend jeans and cropped pants.

Here is an assortment of slip-on sneakers across a range of price points, patterns and colours. Create an on trend look with this casual shoe. 

• Vans Classic Slip-On Core Classics: This true classic for $47, for both men and women, needs little introduction. It’s available in colour blocked checkerboard prints and solid colours. Add a cushioning insole for extra footbed comfort. Here’s the same style in patterns. Read the rave reviews.
• Sperry Top-sider CVO Twin Gore Sneaker: A little glitz for Team Magpie. Might run half a size large. 
• Salvatore Ferragamo Pacau Sneaker: Impeccable quality and comfort. Modern and refined. 
• Zara Printed Leather Slipper with Track Sole: These were quite comfortable and good for wider feet. Great mauve and burgundy snakeskin pattern. Add a cushioning insole. 
• Vince Blair 7 Snakeskin Slip-On Sneaker: Graphic, sleek and comfortable. Size down because it runs large. Read the rave reviews. 
• Kenneth Cole New York King Sneaker: Fun patterns, well made, super comfy and runs quite wide, but true to size. 
• Sam Edelman Becker Slip On: Comfortable but size down at least half a size. 
• Steve Madden Ecentric Sneaker: Textured leather in cute solids and a few patterns. Runs a little small. 

Remember that if you’re wearing slip-on sneakers without socks, footies or Bodyglide will increase their comfort factor.

A couple of years ago, I described our current fashion era as being very accepting of all sorts of outfit juxtapositions, colours, fabrications and silhouettes. Today’s more liberal approach to fashion — where trends do not rule the way we dress like they used to, and where there is no one way to be stylish — has resulted in a rebirth of personal style. Much of the newness in fashion these days comes from how you reinvent and remix items your way. 

With this in mind, there are five things that, to me, epitomize the look for 2014:  

1. Irregular Outfit Juxtaposition: Unexpected item combinations are fashionable. Top of the list is remixing super casual with super formal elements in one outfit; like wearing ball gowns with slip-on sneakers, sequins with shredded jeans, tuxedo jackets with track pants, and beanies with suits. Seasonally confused outfits have never been more on trend.  
2. Just Enough Structure: Fluid and oversized fits that are pretty shapeless, both on the top and bottom, are extremely trendy. Creating just enough structure in an outfit is key to making you look and feel attractive. It’s not a case of an outfit looking conventionally flattering. It’s more a case of an outfit looking “flattering enough”. 
3. Combining the Classics with Trends: This is a personal favourite. Take true classics, like button-down shirts, simple silk blouses, crisp formal suits, pencil skirts, straight leg jeans, bootcut trousers, Gucci-esque loafers, moto jackets, Chanel-esque jackets, Burberry-esque trench coats, denim jackets, denim shirts, riding boots, fitted turtlenecks, Doc Martens boots, pointy toe pumps and ballet flats. Then mix them up with trendy pieces. For example, wear classic Salvatore Ferragamo loafers with slouchy and faded boyfriend jeans, a roomy upscale sweatshirt, studded belt, big watch, and clutch.
4. Hip to Be Square: So called nerdy, frumpy and conventionally unfashionable looks are actually fashion forward. I have my suspicions that Geek Chic eyewear paved the way for this trend. Runway shows and street style photo blogs are full of this type of look. Things are frumpy right up until they become fashionable, and it’s such a fine line. 
5. High-Low style: This is another personal favourite because it re-enforces my philosophy of leaving no retail stone unturned. Combining high-end designer pieces with more affordable pieces in one outfit is fun. Having a wide range of price points represented in your wardrobe can provide a lot of flexibility. Personally, I find this way of dressing empowering and liberating. 

Modern style is about creating your own look, which INCLUDES wearing conventionally flattering outfits. So don’t think that wearing tailored clothing and highly structured outfits in expected combinations is dated. Not at all. In fact, some of the most stylish people in the world stick to dressing in this way and look killer season after season. The point is that you have a choice because that’s the way fashion and style has evolved. Update your classics, choose the trends that appeal the most to you and wear them in ways that make YOU feel fabulous.