How to Wear Derby Shoes?

Are you keen on wearing derby shoes but wondering what to wear them with? How do you match them to your everyday style?

I’m here to help you.

As a fan of bohemian fashion, I really love derby shoes, as they add a touch of elegance to a boho look, while still being very comfortable to wear and compatible with an active lifestyle.

That's why today I'm bringing you a complete guide dedicated to these stylish and feminine shoes, so you can also incorporate them into your wardrobe!

Derby shoes are versatile enough for everyday wear as well as special occasions, making them a great choice if you're looking for comfortable shoes that are easy to pair with outfits. If you're petite or slim, a wedge style will enhance your silhouette beautifully. You can wear your derby shoes with tailored trousers or leather pants for a chic and sexy look, or opt for jeans or cropped fabric pants for a more casual vibe. They also pair nicely with a flared bohemian dress or skirt. And if your legs are on display, be sure to choose thin socks that match your shoes for a polished finish.

Want to find out more details? Keep reading to discover:

• When to wear derby shoes,
• Which ones to choose based on your body shape,
• What style, colour, and material to pick for your derbies,
• What trousers, skirts, or dresses to pair with derby shoes,
• And plenty of outfit ideas illustrated to inspire you!

What are Derbies?

These flats or low-heeled shoes are secured with laces or buckles. They don't rise above the ankles, making them quite low-cut. Typically made of leather, they originated from another type of shoe, the Oxford. However, they are generally easier to put on and take off compared to the Oxfords.

These are essentially men's shoes, which have been reimagined for women, making them more refined and focusing on the details and the quality of the material.

When chosen in the right size and with enough width for the feet, derby shoes can be very practical as they are both stylish and comfortable. They complement a feminine look as well as an androgynous style and can be worn for both everyday occasions and special events.

How to Choose the Right Derby Shoes?

Thinking of trying out derbies but haven't taken the plunge yet? Let me share some simple tips to help you find the perfect pair that fits your style!

Can I wear derby shoes if I'm petite? Or curvy?

We often think that derby shoes are only for tall women with an athletic build. However, that's not the case at all: you just need to find the right style that suits your body shape. If you're petite, curvy, or both, I recommend going for a wedge style, which not only looks super trendy but also enhances your silhouette by elongating your legs.

What colour of derby shoes should you wear?

Derbies come in a variety of colours, but the most popular ones are black and brown. These are classic choices and are perfect for a chic and elegant look. Choose black if you have other elements in your outfit that are also black, to create a colour coordination. The same goes for brown, which will give a more bohemian style. If your outfit is light-coloured, consider going for beige or white derbies.

However, if you're looking to explore beyond the usual paths, you can definitely choose to:

• A shade that contrasts with the rest of your outfit: like white derby shoes with a black suit, for example,
• A vibrant colour (red, teal, fuchsia pink...) that you can wear as an accent matching a small piece of your outfit in the same shade, or even as a total look for a high-fashion effect!
• Metallic derbies to brighten up your outfit and give it an unmatched style!

Which model should you choose?

Although there are other materials, most derbies are made of leather or suede. I recommend choosing these materials as they are easy to maintain and durable.

The style you choose will depend on the outfits you want to wear with your derby shoes:

👗 When wearing a dress or a skirt, it's best to go for round or semi-round shoes for a feminine and elegant look.

👖 When it comes to trousers, like tailored ones for example, I recommend pairing them with semi-pointed or pointed derby shoes to achieve an ambitious style and a couture look.

What socks to wear with derby shoes?

This question might seem a bit odd, but it's worth considering. In fact, there are two ways to wear derbies if your legs are on display:

• by hiding your socks and opting for thinner ankle socks,
• by making your socks visible to create a vintage and unique look.

If you choose the second option, go for thin socks that don’t rise too high on your legs. Light colours are generally more stylish, and the best choices are socks made from crochet or lace. Gather your socks slightly at the bottom of your leg to create a nice overall look.

What trousers to wear with derby shoes?

Thinking of wearing your derbies with trousers? Let’s explore together what would suit you based on your style and preferences.

A tailored trouser

Worn with a blazer and tailored trousers, derby shoes are perfect for completing a very elegant look. Slightly androgynous while remaining feminine and chic, this type of outfit is ideal for standing out at a special event, showcasing your ambition and motivation during a job interview, or simply looking ultra-classy for a night out with friends.

👉 For a high-fashion look, go for a matching suit with bold patterns paired with shiny black derbies to complete the outfit perfectly!

A leather pant

With leather pants, a white blouse or shirt, and some derby shoes, you’ll achieve a contemporary and sexy look. This is perfect for a night out, for a romantic date, or even for everyday wear if you want to showcase your passion for fashion.

👉 I recommend going for matte shoes to create a nice contrast with the shiny look of these types of pants.

A pair of jeans

Would you describe your style as casual chic? If so, know that your derbies will pair perfectly with slim or boyfriend jeans. The key is to ensure that the pants are tapered at the ankles, creating an optical effect that showcases your legs nicely.

👉 As such, it’s best to steer clear of flared jeans or bell-bottoms, as they clash too much with the smart look of derby shoes and would not do them justice.

A cropped pant

If the weather's nice, why not pair your derbies with a lighter outfit? A lovely plain or patterned cropped trouser would be perfect to elevate your look. This way, you’ll have an ideal outfit for heading to work, university, or taking a walk in the city during the beautiful season!

What skirt to wear with derby shoes?

If you prefer to wear a skirt with your derbies, here are some outfit ideas that might interest you!

A Short Flared Skirt

For an ultra-cute and very feminine look, this is the option you should go for! If it's a bit chilly, don't hesitate to wear tights, which will only enhance your derbies. This look is both adorable and comfortable, making it perfect for university, spending a day with friends, or boosting your chances for a first date!

A Pleated Maxi Skirt

The pleated maxi skirt has been very trendy in recent years, combining both elegance and versatility. It’s really easy to wear and flatters most body types. Just make sure that your skirt falls below your knees and not above your ankles, as that could make your silhouette appear a bit shorter!

Dare to wear the mini shorts!

Looking for a light and lively outfit? One that lets you move freely? You can easily pair derby shoes with a mini shorts look to create a sexy ensemble that showcases your legs! The derby shoes will add a touch of chic to the shorts, making the outfit smart and stylish:

• a going out outfit, featuring black leather or fabric shorts paired with tights,
• a summer outfit, consisting of solid-colour or patterned fabric shorts.

How to Wear a Dress with Derby Shoes?

Just like skirts, you can definitely pair a dress with derby shoes. For instance, you could wear a skater dress, whether it's short or long, which, similar to a flared skirt, will be great for showcasing your legs.

If you prefer a boho-chic look, don't hesitate to choose a midi dress that falls below the knees, made of lace or featuring embroidery. This will give you a very feminine style, perfect for those lovely summer days.

I hope this article has inspired you to rock a pair of derbies, no matter the occasion or your body type! This chic footwear is sure to become a staple in your wardrobe! 😉

And if you're looking for a stylish and feminine dress or outfit to pair with your derbies (or any other shoes!), check out our chic bohemian clothing collections! You'll find trendy dresses and skirts designed to flatter your figure and boost your confidence!

Bohemian Maxi Dress