How to Style Ballet Flats & Mary Janes Shoes

There was a time when Mary Janes and ballet flats conjured up images of dance recitals and the school playground. Mary Janes, a term coined Stateside for bar or doll shoes, were seen everywhere from classrooms to the red carpet throughout the nineties. Characterised by a single bar strap across the instep, this style could be seen on all the well-heeled celebrities of their heyday, from Winona Ryder to Sandra Bullock.

Fast-forward a few years to a time when women’s ballet flats were popularised both on and off the runway by the London It-girls of the noughties. Alexa Chung’s low-effort, max-impact ballet flats and denim skirt combination oozed indie-sleaze. While Kate Moss paraded in her signature noughties uniform: skinny jeans and a military jacket, signed off with simple black ballet pumps.

So, are Mary Jane shoes in style? Are ballet pumps? Thanks to a wave of nineties and noughties nostalgia and the 2022 spring-summer revival, Mary Janes have once again cemented themselves firmly as wardrobe staples, rather than passing trends.

At Jones Bootmaker, we’ve embraced the child-like simplicity of these timeless silhouettes. Showcasing slimline, flat-soled designs, crafted from butter-soft leather with minimalist details. Adopting the mantra that simple is chic. This guide is designed to help you find, and confidently style, your new favourite pair of Mary Jane shoes and ballet flats.

Here’s what we’ll cover:

• How to wear ballet flats
• How to wear Mary Jane shoes
• Ballet flats vs Mary Janes - which should you choose?

How to Wear Ballet Flats

The simplicity of ballet flats allows you to be bold when choosing the cuts, prints, and colours of your clothes. A shorter skirt with ballet flats will give the appearance of longer legs thanks to the shoe’s open top design.

A perfect shoe for the commuters among us, there’s no need to worry about rolling your ankle with the ballet flats’ comfortable, cobble-friendly profile. Paired with a midi dress or skirt, ballet flats can take you from daywear to evening in a flash. Just switch out your slouchy tote bag (note Kate Moss circa 2005) for a clutch or handbag.

Choose a pump in a single colour for maximum versatility. Black is the safest option if you’re undecided. Black ballet pumps will look effortlessly smart alongside your working week ensembles and your weekend denims. Black tights pair effortlessly with black ballet pumps, extending their wear seamlessly into the cooler months.

How to Wear Ballet Flats with Jeans

For an injection of noughties nostalgia, pair your ballerina pumps with skinny or drainpipe jeans. For a contemporary twist on this noughties classic, choose an ankle-grazing style for a more clean-cut aesthetic.

Versatile as they are, there are very few cuts of jeans that ballet flats can’t handle. For looser cuts of jeans, such as flared, wide-leg, or ‘mom’ jeans, slip on your ballet pumps with a matching belt to maintain a sense of streamlined structure throughout your look. Ballet flats can disappear under a full-length, wide leg, so opt for a cropped or leg to keep the shoe on show.

Colour-wise, black ballet flats go great with dark denim for an evening look, while neutral or tan flats with light-wash denim flourish during the daytime.

How to Wear Ballet Flats with Dresses & Skirts

The delicate silhouette of a ballet flat complements the femininity of dresses and skirts perfectly. We’ve mentioned ballet flats with midi dresses or short skirts already; if you’re choosing this combination, a shorter hemline maximises the leg-lengthening effect.

Flats with a maxi dress is a riskier pairing, due to the potential dragging of the hem. If you’re wedded to this combination, choose a slightly cropped maxi or one with a front split.

For evening wear, ballet flats with a metallic finish really come to life.

What Colour Ballet Flats to Choose?

Black is the safest option for a lot of outfits, as we’ve mentioned, but there are some other key colour considerations to keep in mind:

• Nude or tan is the closest you’ll get to skin tone and works well to elongate the leg. These colours work with pretty much anything, too.
• White or cream is fresh and clean, ideal for spring and summer, and pairs perfectly with denim and pastel.
• Metallic gold or silver is ideal for evenings, bringing a dressier finish without compromising on comfort.

How to Wear Mary Jane Shoes

Mary Janes have a dual heritage: first associations with childhood and school, then their reclamation as a stylish wardrobe staple. The characteristic bar strap changes the look and the styling logic when compared with a ballet flat. In this section, we explore the ideal pairings for this iconic style.

What to Wear with Mary Janes

The same rules apply for your flat Mary Janes when it comes to colour. A single block colour will serve you well when looking for a shoe you’ll want to wear anywhere, everywhere.

In terms of cut, match the clean lines of your Mary Janes to more structured cuts of clothing. Ankle-grazing jeans and sharp tailoring will match the tone of your Mary Janes – but that doesn’t mean you should avoid looser-fitting clothes. Why not pair your Mary Janes with an oversized blazer for a relaxed yet refined appeal?

These shoes also work very naturally with dresses: shirt dresses or A-lines specifically, with the strap adding a feminine, vintage-inspired edge.

Socks and heel height can also change the notes Mary Janes bring to an outfit - we’ll look at each of these in turn in the following sections.

Socks with Mary Janes

The right pair of socks can change the tone of your Mary Janes in an instant. Opt for white socks if you’re looking to lean into their childlike quality, or black socks with black Mary Janes for a little Parisian edge.

A simple switch from opaque socks to sheer mesh is a sure way to make a statement and offers an easy way to elevate your Mary Jane ensembles for evening wear or more formal occasions.

You can also play with length: ankle socks accentuate the playful, youthful energy, while knee-high socks lean intentionally into the vintage schoolgirl aesthetic. Textured or patterned socks can bring visual interest without changing your shoes.

Heeled Mary Janes vs Flat Mary Janes

The bar strap defines Mary Janes regardless of heel height, but this property can vastly change the appearance of a Mary Jane outfit. Flat Mary Janes are great for everyday wear, casual through to smart-casual, and forgiving on your feet. Lightly heeled Mary Janes, on the other hand, cross confidently into evening and occasion territory.

A kitten heel or block heel adds height while retaining the stability of the style, making them a practical choice for longer evenings. Pair a heeled Mary Jane with a short dress or skirt for a strong, simple combination: the strap will draw the eye to the ankle, allowing your whole outfit to shine.

Ballet Flats vs Mary Janes - Which Should You Choose?

This is about choosing the right pair for you, not declaring a winner of which shoe is best. Here are some guiding thoughts:

• Ballet flats are versatile everyday shoes with a lower profile and a wider outfit compatibility. They’re the ideal grab-and-go shoe. Choose them when you want a casual look where the outfit leads.
• Mary Janes have more character and lend themselves to more intentional styling. Choose them when you want the shoes to be part of the look.

Ready to Find Your Dream Pair of Ballet Flats?

Both ballet flats and Mary Janes are timeless, and both have earned - and proven - their place in any wardrobe. To find your next favourite pair, take a look at our range of Mary Janes[KMM1] and ballet flats. We hope this guide has given you the information to wear - and pair - your new shoes with confidence.