Kickin' It Old School: What Shoes Do You Wear with Bell Bottoms? (Masculine Looks)

Are you ready to step back in time and embrace the groovy, retro vibes of bell bottoms? If you want to rock a masculine look that harkens back to the '70s, you're in for a style adventure like no other.

Picture this: you're suiting up in your favorite pair of bell bottoms, exuding an unmistakable air of vintage coolness. But hold on a minute – before you strut your stuff, there's a style conundrum that deserves your attention. The shoes! Yes, my fashion-savvy friends, shoes can either make you a style icon or leave you wondering where you went wrong.

We understand your desire to make a statement, whether hitting the town, catching up with friends, or embracing life's everyday adventures. The right shoes can be the secret ingredient that takes your bell bottom game from ordinary to extraordinary.

It's time to kick it old school, quite literally! Today, we're diving into the fascinating world of pairing shoes with bell bottoms. Whether you're a sneaker enthusiast, a fan of dashing dress shoes, or somewhere in between, get ready for tailored recommendations that elevate your bell-bottom style game. So, grab those bell bottoms, and let's embark on a journey through time and fashion – one that will have you strutting your stuff with flair and leaving a lasting impression wherever you go. Get ready to kick it old school!

A Moment of Appreciation for Bell Bottoms

Before delving into the details of selecting shoes, let's take a moment to appreciate the charm of bell bottoms. Consider this: bell bottoms are akin to the fashion equivalent of a mullet—business on top, party on the bottom. And let's be frank, who can resist a good party?

Bell bottoms, also called flares or flared pants, boast a storied history dating back to the 18th century. They initially served as practical garments for British and US Navy sailors. These wide-legged trousers facilitated easy movement on deck and could be rolled up to knee-length to keep sailors comfortable. Moreover, they possessed the added advantage of quick removal in emergencies, doubling as makeshift life jackets.

During the 1960s and 1970s, bell bottoms became a celebrated fashion statement for individuals of all genders, aligning with the ethos of the hippie and bohemian movements. They were frequently fashioned in vibrant colors and eye-catching patterns, often paired with other iconic fashion elements of the era, including tie-dye shirts and fringed jackets.

While the popularity of bell bottoms waned in the 1980s, they experienced multiple resurgences, enjoying renewed acclaim in the 1990s, early 2000s, and more recently in the 2010s.

Bell bottoms are a sought-after fashion item in contemporary times, frequently showcasing modern styles, prints, and fabrics.

The Basics of Shoe Pairing with Bell Bottoms

Pairing the perfect shoes with bell bottoms is an art that can elevate your style game to new heights. But like any art form, it requires careful consideration and a dash of creativity. Let's explore the essential factors to contemplate when selecting the ideal footwear to complement your bell bottoms.

1. The Pant Color

The color of your bell bottoms sets the tone for your entire ensemble. Whether you're sporting classic denim or vibrant patterns, here's what to keep in mind:

Contrast or Blend: Opt for shoes that contrast with your bell bottoms for a statement look. Light-colored shoes will pop if your pants are dark, and vice versa. Alternatively, choose shoes that harmonize with the color palette of your pants for a more balanced appearance.
Monochromatic Magic: Matching your shoes to the exact shade of your bell bottoms can create a sleek, monochrome effect that elongates your silhouette.

2. The Occasion

Your choice of footwear should align with the event or activity at hand. Here's how to navigate different occasions:

Casual Cool: If you're rocking bell bottoms for a casual outing, consider comfortable sneakers, espadrilles, or loafers. These options exude a relaxed vibe and keep you at ease.
Formal Finesse: For more formal occasions, like weddings or business meetings, polished dress shoes or boots are the way to go. They exude sophistication and refinement, complementing your bell bottoms elegantly.

3. The Weather

Don't let unexpected weather rain on your fashion parade. Be prepared:

Sunny Days: When the sun is shining, embrace sandals, canvas shoes, or espadrilles to keep your feet cool and comfortable.
Rain or Chill: Opt for closed-toe shoes or boots with good traction to keep your feet dry and secure in wet or cold conditions.

Pairing the perfect shoes with bell bottoms is an art that's as versatile as your own personal style. By considering factors such as pant color, the occasion, and the weather, you can create ensembles that are not only fashionable but also functional. So, step into your bell bottoms with confidence, knowing that your choice of footwear will complete your look in a way that's uniquely you.

Pairing 1: Sandals

Strappy sandals offer a casual and comfortable option that complements the free-spirited vibe of bell bottoms. They're ideal for warm weather, ensuring your feet stay cool and ventilated. The open design of strappy sandals also allows you to showcase your fashion-forward side.

Opt for earthy tones like brown or tan to create a harmonious, bohemian look. Ensure the length of your bell bottoms grazes the top of your sandals for a balanced appearance. Wear a tucked-in white T-shirt or a loose-fitting button-up shirt to complete the laid-back ensemble.

This combo is perfect for casual outings, beach trips, or music festivals. Strappy sandals with bell bottoms exude a relaxed, carefree aura ideal for daytime adventures and outdoor events. Don't forget your sunglasses and a wide-brimmed hat to complete the effortlessly cool look.

Pairing 2: Espadrilles

Espadrilles offer a stylish and versatile option for men wearing bell bottoms. Their lightweight canvas or linen construction provides comfort, while the jute rope sole adds a touch of summer flair. Espadrilles effortlessly blends classic and contemporary styles, making them a go-to choice.

Opt for a navy or neutral-colored espadrille to maintain a balanced color scheme. Roll the hems of your bell bottoms slightly to reveal the espadrilles, creating a relaxed and tailored appearance. Complement this combo with a fitted white linen shirt or a striped tee for a nautical twist.

This ensemble is perfect for beach vacations, casual garden parties, or daytime gatherings. Espadrilles with bell bottoms offer a laid-back yet refined look that suits warm-weather occasions. Don't forget to accessorize with a woven belt and a fedora hat to complete the effortlessly chic summer outfit.

Pairing 3: Sneakers

Canvas or low-top sneakers are a fantastic choice for a laid-back yet stylish look with bell bottoms. They offer comfort, versatility, and a youthful edge. The simplicity of these sneakers allows them to complement the statement style of bell bottoms effortlessly.

Opt for white or classic black sneakers to keep the focus on your bell bottoms. Ensure the length of your pants slightly covers the top of your sneakers, creating a clean and elongated silhouette. Pair with a graphic tee or a retro-inspired shirt for a casual, vintage feel.

This combination is perfect for weekend outings, casual dinners, or music events. Canvas or low-top sneakers with bell bottoms offer a relaxed, street-style, comfortable, and fashionable look. Add a baseball cap and subtle accessories to complete the effortlessly cool ensemble.

Pairing 4: Loafers

Loafers, whether tassel or penny, bring a touch of sophistication to bell bottoms. These shoes effortlessly blend comfort and class. They offer a polished and timeless appearance that contrasts nicely with the relaxed nature of bell bottoms.

For a refined look, choose classic black or brown leather loafers. Ensure your bell bottoms are tailored to break slightly above the top of your loafers. Pair them with a tucked-in dress shirt or a lightweight knit sweater. Add a leather belt in a matching shade to tie the look together.

This combination is ideal for semi-formal occasions like dinner parties, date nights, or business-casual events. Loafers with bell bottoms project an image of sophistication and taste. Consider wearing a blazer for a more upscale appearance or opt for a casual blouson jacket for a smart-casual ensemble.

Pairing 5: Boat Shoes

Boat shoes combine comfort and style effortlessly, making them a practical choice with bell bottoms. Their nautical origins and non-slip soles offer a hint of adventure and functionality. Boat shoes in leather or canvas provide durability and timeless appeal.

Opt for earthy tones or classic navy boat shoes to complement the bell bottoms' retro vibe. Ensure your pants skim the top of the shoes for a balanced look. Pair with a lightweight, striped sweater or a casual button-down shirt for a relaxed, coastal feel.

This combination is perfect for outdoor gatherings, brunches, or casual seaside escapes. Boat shoes with bell bottoms offer a laid-back, preppy aesthetic perfect for warm-weather occasions. Consider adding a braided belt and a pair of stylish sunglasses to complete the breezy, maritime-inspired ensemble.

Pairing 6: Driving Shoes

Driving shoes are the epitome of relaxed elegance, making them an excellent companion for bell bottoms. Crafted for comfort and style, they feature soft, supple leather and rubber pebble soles that offer superior grip. This combination ensures a seamless blend of fashion and functionality.

Opt for driving shoes in versatile shades like brown or navy to complement the bell bottoms' retro aesthetic. Bell bottoms should hover just above the heel of the shoes, creating a clean line. Pair them with a well-fitted polo shirt or a lightweight knit for a polished yet casual appearance.

This ensemble is perfect for weekend getaways, casual lunches, or outdoor events. Driving shoes with bell bottoms project an air of sophistication with a hint of relaxation. Add a leather wristwatch and a simple belt to elevate the look, making it suitable for day and evening affairs.

Pairing 7: Moccasins

Moccasins offer a fusion of comfort and style, making them a versatile choice with bell bottoms. Their soft, supple leather and distinctive stitching exude a casual yet refined charm, aligning perfectly with the bell bottoms' vintage flair.

Opt for classic earthy tones like brown or tan for your moccasins to complement the relaxed aesthetic of bell bottoms. Ensure your pants graze the top of the shoes for a balanced look. Pair them with a lightweight linen shirt or a casual blazer for a smart-casual ensemble.

This combination is ideal for casual gatherings, weekend brunches, or a day at the office with a relaxed dress code. Moccasins with bell bottoms offer a laid-back, sophisticated style that's suitable for a range of occasions. Add a leather belt and a pocket square to elevate the look, making it versatile enough for daytime and evening events.

Pairing 8: Dress Shoes

Dress shoes like monk straps, Oxfords, or Derbys offer a sophisticated contrast to the relaxed silhouette of bell bottoms. These shoes exude elegance and refinement, creating a harmonious blend of formal and casual elements.

Choose classic black or brown leather dress shoes to maintain a timeless appeal. Ensure your bell bottoms have a slight break above the shoe to showcase their clean lines. Pair with a well-tailored blazer and a crisp white dress shirt for a polished yet relaxed look.

This ensemble is perfect for semi-formal events, date nights, or upscale dinners. Dress shoes with bell bottoms project an image of sophistication and style, making them suitable for evening occasions where you want to make a statement. Don't forget to add a sleek leather belt and a well-kept hairstyle to complete the dapper outfit.

Pairing 9: Boots

Boots provide a rugged and bold pairing option for bell bottoms. Whether it's Chelsea boots for a sleek look, Chukka boots for versatility, or Cowboy boots for a touch of Western charm, they add a unique edge to your outfit while offering excellent ankle support and durability.

Select boots that resonate with your personal style: Chelsea boots for a modern edge, Chukka boots for a versatile approach, or Cowboy boots for a distinctive flair. Ensure your bell bottoms skim the top of the boots for a balanced appearance. Complement them with a relaxed-fit graphic tee or a denim shirt for a rugged yet stylish ensemble.

This combination suits outdoor concerts, casual gatherings, or nights out with friends. Boots with bell bottoms evoke a sense of adventure and confidence. Consider adding a leather jacket and a statement belt buckle to enhance the look, making it perfect for showcasing your individuality at daytime and evening events.

Pairing 10: Platform Shoes

Platform shoes, with their distinctive elevated soles, are a bold choice that perfectly complements the exaggerated flare of bell bottoms. They add height and a sense of retro flair to your outfit, making a strong fashion statement.

Choose platform shoes with a classic '70s vibe in neutral tones like black, white, or brown. Allow your bell bottoms to sweep gracefully over the platform soles for a dramatic effect. Opt for a fitted, solid-colored turtleneck or a patterned button-up shirt to balance the boldness.

This look is excellent for themed parties, concerts, or creative events where you want to stand out. Platform shoes with bell bottoms create a distinctive, attention-grabbing ensemble that exudes confidence. Consider adding oversized sunglasses and a funky hat to enhance the retro vibe, making it suitable for daytime and nighttime affairs.

Top Picks: Shoes to Wear with Bell Bottoms

When pairing your bell bottoms with the perfect shoes, the options are as diverse as your personal style. We've curated a list of top shoe picks to complement your bell bottoms, whether you're aiming for a sophisticated, edgy, or laid-back look.

Gucci Horsebit Loafers: These iconic loafers perfectly match dressier bell bottoms. The sleek and sophisticated shoe design complements the bell bottoms' flare, creating a balanced and cohesive look.
Dr. Martens 1460 Boots: These boots are an excellent option for those looking for a more edgy and alternative look with their bell bottoms. The chunky and sturdy design of the boot adds a touch of toughness to the outfit while still looking stylish.
Salvatore Ferragamo Parigi Loafers: These sleek and polished loafers are an excellent option for those looking for a more sophisticated look with their bell bottoms. The shoe's high-quality leather and classic design make it a versatile choice for dressy or casual occasions.
Common Projects Achilles Low Sneakers: These minimalist and sleek sneakers are an excellent option for a more modern and streamlined look with their bell bottoms. The shoe's simple design and high-quality materials make it a versatile choice for dressy or casual occasions.
Church's Consul Oxford Shoes: These classic Oxford shoes are an excellent option for a more formal and dressy look with bell bottoms. The shoe's high-quality leather and polished design make it a versatile choice for formal occasions.
Vans Old Skool Sneakers: These classic sneakers are an excellent option for those looking for a more casual and laid-back look with their bell bottoms. The simple and classic design of the shoe makes it easy to pair with different bell bottom styles and colors.
Cole Haan Pinch Tassel Loafers: These classic and timeless loafers are a great option for those looking for a more sophisticated and polished look with their bell bottoms. The high-quality leather and tassel detail adds a touch of elegance to the outfit while still looking stylish.
Birkenstock Arizona Sandals: Embrace warm weather and casual charm with these classic strappy sandals. The timeless design pairs effortlessly with bell bottoms for a relaxed, summery look.
TOMS Alpargata Espadrilles: Achieve a breezy, Mediterranean-inspired vibe with these espadrilles. Their simple canvas design and rope sole bring a touch of casual elegance to your bell bottom ensemble.
Sperry Authentic Original Boat Shoes: These boat shoes are the go-to choice for a preppy and nautical-inspired look. These classic boat shoes exude timeless style and pair seamlessly with wide-legged bell bottoms.
Tod's Gommino Driving Shoes: Slip into luxury with these driving shoes. These Italian-made beauties combine comfort and sophistication, making them an ideal complement to your bell bottoms for a refined casual look.
Minnetonka Classic Moccasins: These moccasins offer a touch of boho-chic, pairing effortlessly with bell bottoms. These comfy, fringe-adorned shoes add a free-spirited flair to your ensemble.
Stella McCartney Elyse Platform Derby Shoes: If you want to make a bold fashion statement, these are your answer. Their striking design adds height and drama to your bell bottom outfit, creating a unique, attention-grabbing look.

The shoes you pair with bell bottoms can significantly influence your overall look and style. With these top shoe picks, you can create stunning bell-bottom outfits that turn heads and make a lasting impression.

Bell bottoms have made a triumphant comeback, and they're not just for the fashion-forward everyday folks. Celebrities have embraced this iconic trend with flair, showcasing their unique style and proving that bell bottoms are here to stay.

Billy Porter: was seen wearing a pair of sparkly bell bottoms with a matching blazer and shirt. The look was finished with platform shoes, adding height and drama to the outfit.
Harry Styles: has been spotted wearing a variety of bell-bottom styles, including brightly colored pairs and patterned pairs. Pairing them with everything from printed shirts to classic t-shirts and sneakers to heeled boots.
ASAP Rocky: has been spotted wearing bell bottoms in various colors and materials, including leather and denim. Pairing them with everything from graphic tees to blazers and sneakers to dress shoes.
Shawn Mendes: wore a pair of black bell bottoms with a printed shirt and leather jacket. The look was finished with dress shoes, adding a touch of sophistication to the edgy outfit.
Machine Gun Kelly: wore a pair of black leather bell bottoms with a black t-shirt and leather jacket. The look was finished with boots, adding a touch of edginess to the outfit.
Timothée Chalamet: was seen wearing bell bottoms in casual and formal settings. Pairing them with everything from hoodies to blazers and sneakers to dress shoes.

Whether you're aiming for a daring, edgy look like Machine Gun Kelly or seeking sophisticated charm like Shawn Mendes, bell bottoms offer a versatile canvas for self-expression. As these trendsetters demonstrate, bell bottoms can seamlessly transition from casual to formal settings, proving they are indeed a fashion statement worth embracing. So, take cues from these style icons and let your bell bottoms shine in your unique way.

Tips from Our Editors

Add Dimension: Be creative by experimenting with various textures for your shoes and bell bottoms. For instance, you can pair suede shoes with denim bell bottoms or leather footwear with velvet flares. This adds an intriguing dimension to your outfit, ensuring it stands out in style.
Harmonize Colors: Take into account the color of your chosen shoes. Classic neutral tones like black, brown, or gray harmonize seamlessly with most bell-bottom styles and shades. Alternatively, you can opt for bolder hues or patterns to infuse a unique character into your look.
Regular Cleaning: The condition of your footwear plays a pivotal role in shaping your overall outfit's impression. Cultivate the practice of regularly cleaning and polishing your shoes to enhance their visual appeal, elevating the overall aesthetic of your ensemble.
Proper Storage: When your shoes are not adorning your feet, proper storage is imperative. Identify a cool, dry location shielded from direct sunlight to ensure optimal preservation. Utilize shoe trees or delicately pad them with tissue paper to maintain their shape and prevent unsightly creases.

On a Final Note

It's evident that fashion has an incredible way of looping back through the ages, and bell bottoms are a testament to that time-traveling trendiness. By now, you've mastered the art of pairing the perfect shoes with your masculine bell bottoms, and you're ready to conquer any event or casual hangout confidently.

Remember, your style journey is an ever-evolving adventure. So, whether you're strutting your stuff at a formal event, unleashing your inner groove during a night out, or embracing spontaneous escapades, let your choice of footwear be the exclamation point to your ensemble.

In a world of ever-changing fashion fads, bell bottoms are a timeless symbol of self-expression and individuality. So, keep kickin' it old school with your fabulous footwear choices, and may your fashion adventures be as groovy as your soul. Stay stylish, stay timeless, and let your style continue to make waves through the ages.