How to Style Derby Shoes?

Do you want to wear dress shoes but are wondering what outfits to wear them with? How can you incorporate them into your everyday style?

I will help you.

As a fan of bohemian fashion, I really love derby shoes, which add a touch of elegance to a boho look while being very comfortable to wear and suitable for an active lifestyle.

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

Derbies can be worn every day as well as for special occasions, and they are perfect if you’re looking for comfortable shoes that are easy to match. If you’re slim and/or petite, a wedge style will be great for enhancing your figure. You can pair your derbies with tailored pants or leather trousers for a chic and sexy look, or with jeans or fabric capris for a more casual vibe. They also pair beautifully with a flowing dress or a flared bohemian skirt. Lastly, if your legs are visible, opt for thin socks that match your shoes.

Want to learn more? Keep reading to find out:

• When to wear derby shoes,
• Which ones to choose based on your body type,
• What style, color, and material to select for your derby shoes,
• What pants, skirt, or dresses to pair with derby shoes,
• And plenty of outfit ideas illustrated to inspire you!

What are Derbies?

These flat shoes or those with small heels are secured with laces or buckles. They do not rise above the ankles, so they remain quite low. They are typically made of leather and are derived from another style of shoe, the Oxford shoes. However, they are much easier to put on and take off than the latter.

These are essentially men’s shoes that have been reimagined for women by refining their design and focusing on the details and the quality of the materials.

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

How to Choose the Right Derby Shoes?

Would you like to try derby shoes but haven’t taken the plunge yet? I’m sharing some simple tips to help you find the perfect pair that matches your style!

Can I wear dress shoes if I’m short? Or curvy?

There’s often a belief that derby shoes are only for tall women with an athletic build. However, that’s not the case: you just need to find the right style that suits your body shape. If you are short, curvy, or both, I recommend choosing a wedge style, which, in addition to being ultra-trendy, will enhance your silhouette by elongating your legs.

What Color of Derby Shoes to Wear?

Derby shoes come in a variety of colors, although the most commonly worn are black and brown. These colors are classic and perfect for achieving a chic and elegant look. If your outfit includes other elements in black, it’s best to choose black derbies to create a cohesive color scheme. The same goes for brown, which will give you a more bohemian style. If you’re wearing lighter colors, consider beige or white derbies instead.

However, if you’re looking to stray a bit off the beaten path, you can definitely choose:

• A shade that contrasts with the rest of your outfit: white derbies with a black suit, for example.
• A vibrant color (red, teal, fuchsia pink…) that you can wear to match a small element of your outfit in the same hue, or even in a total look for a high-fashion effect!
• Metallic derbies to illuminate your outfit and give it an unmatched style!

Which Model Should You Choose?

While there are other materials available, most derby shoes 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 clothing you want to wear with your dress shoes:

👗 When wearing a dress or a skirt, it’s best to choose shoes with round or semi-round toes for a feminine and elegant style.

👖 With dress pants, for example, I recommend semi-pointed or pointed derby shoes to create an ambitious style and a couture look.

What Socks to Wear with Derby Shoes?

This question may seem strange, but it’s important to ask it. In fact, there are two ways to wear derby shoes if your legs are visible:

• by hiding your socks and opting for thin ankle socks instead,
• by showcasing your socks to create a vintage and unique look.

If you choose the second option, opt for thin socks that don’t rise too high on your legs. Lighter colors tend to look more elegant, and the best choice is socks made from crochet or lace. Gather your socks slightly at the bottom of your legs to create a nice overall look.

What Pants to Wear with Derby Shoes?

Would you like to wear your derby shoes with pants? Let’s explore together what might suit you based on your style and preferences.

A Tailored Pair of Trousers

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

👉 For a high-fashion look, dare to wear a matching suit with patterns paired with shiny black dress shoes that will complete the outfit perfectly!

A Leather Pants

Pairing leather pants with a white blouse or shirt and some derby shoes will give you a contemporary and sexy look. This outfit is perfect for a night out, a romantic date, or even for everyday wear if you want to showcase your passion for fashion.

👉 I recommend matte shoes instead, to create a contrast with the shiny look of this type of pants.

A Pair of Jeans

Would you describe your style as casual chic? If so, know that your derby shoes will pair perfectly with slim or boyfriend jeans. The key is that these pants should be fitted at the ankles, creating an optical effect that will accentuate your legs.

👉 Therefore, avoid flared jeans or bell-bottoms, as they clash too much with the stylish look of derby shoes and wouldn’t highlight them properly.

A cropped pant

If the weather is nice, why not wear your loafers with a lighter outfit? A nice, solid or patterned cropped pant would be perfect to elevate your look. This way, you’ll have the ideal outfit to head to work, university, or take a stroll around the city during the warm season!

What skirt to wear with derbies?

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

A Short Skater Skirt

For an ultra-cute and very feminine look, this is the option you should choose! If it’s a bit chilly, don’t hesitate to wear tights, which will only enhance your derby shoes. This adorable and comfortable look is perfect for heading to college, spending a day with friends, or making a great impression on a first date!

A Pleated Maxi Skirt

In recent years, the pleated maxi skirt has become a very trendy outfit that’s both chic and versatile. It’s easy to wear and flattering for most body types. Just make sure your skirt falls below your knees and not above your dress shoes, as that could shorten your silhouette a bit!

Dare to Wear a Mini-Short!

Looking for a light and vibrant outfit? One that allows you to move freely? You can definitely pair derby shoes with a mini-short to create a sexy look that showcases your legs! The derby shoes will add a stylish touch to the shorts, dressing them up nicely:

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

How to Wear a Dress with Derby Shoes?

Just like with skirts, you can definitely pair a dress with derby shoes. For example, you could wear a skater dress, whether short or long, which, like a flared skirt, will beautifully highlight your legs.

If you prefer a boho chic look, don’t hesitate to choose a midi dress that falls below the knees in lace or with embroidery. This will give you a very feminine style, perfect for beautiful summer days.

I hope this article has inspired you to wear derby shoes, no matter the occasion or your body type! This pair of stylish shoes will surely become a staple in your wardrobe! 😉

If you’re looking for stylish and feminine dresses or clothing 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 enhance your figure and boost your confidence!

Bohemian Long Dress