Flare Jean Fabulousness: What Shoes Do You Wear with Flare Jeans (Masculine Looks)

Are you ready to step into the world of flare jeans fabulousness and unleash your inner style icon? If you're looking to make a statement with your masculine flair while rocking those trendy flare jeans, then get ready to embark on a sartorial adventure like no other.

Imagine yourself strutting down the street, the wide-leg elegance of your flare jeans catching every eye. You exude confidence and charisma, but here's the twist – the right shoes can take your flare jean game to new heights or send it plummeting into fashion oblivion. Are you willing to take that risk?

We know you crave that undeniable allure, whether strolling into a casual gathering, hitting the town, or expressing your unique style. Your choice of footwear can be the game-changer, enhancing your charm and perfectly complementing your flare jeans for a look that turns heads.

It's time to put your best foot forward, quite literally, and dive into our exclusive shoe-pairing revelations. Whether you're a sneaker fan, a suave boot enthusiast, or navigating the versatile realm in between, we've got the tailored recommendations to elevate your flare jean game. So, grab those fabulous flare jeans and prepare to conquer the fashion world with style and flair (pun intended). Let's embark on this journey together – one that will have you strutting confidently and leaving an indelible mark wherever you go.

Are Flare Jeans in Style Again?

The resurgence of flare jeans in the fashion arena is no coincidence; it's a stylish comeback driven by several compelling factors. Chief among them is the nostalgia factor that tugs at the heartstrings of those who fondly remember the '70s and '90s fashion scenes. For them, the reappearance of flare jeans is a welcome blast from the past while simultaneously introducing a retro-chic aesthetic to a new generation of fashion enthusiasts.

Versatility plays a pivotal role in their revival as well. Flare jeans boast a silhouette that can effortlessly transition from casual to formal, making them a prized addition to any wardrobe. Their adaptability shines as they harmonize effortlessly with various shoe styles, tops, and accessories, granting fashion aficionados a vast spectrum of styling possibilities.

Modern innovation in the fashion world also contributes to the resurgence of flare jeans. Designers and brands have breathed new life into these classics by infusing them with contemporary elements, offering a plethora of fabrics, finishes, and lengths to cater to diverse tastes and preferences.

Celebrity endorsements serve as another powerful catalyst for the resurgence of flare jeans. When trendsetting celebrities and influencers proudly sport these iconic denims, it naturally piques the wider public's interest, propelling the trend even further.

In the ever-cycling world of fashion, trends often reemerge over time, transforming outdated items into vintage and trendy pieces for a new era. Flare jeans are no exception to this cyclical phenomenon.

Furthermore, flare jeans offer individuals a canvas to express their distinctive style and comfort preferences in a world that highly values personal fashion choices. They offer a refreshing departure from the ubiquitous dominance of skinny jeans, allowing individuals to stand out and make a sartorial statement.

Last but not least, the influence of the runway and high-end fashion collections must not be underestimated. When top designers incorporate flare jeans into their collections and showcase them on prestigious runways, it lends a sense of credibility to the trend, hastening its acceptance within mainstream fashion circles.

The Basics of Shoe Pairing with Flare Jeans

Mastering the art of pairing shoes with flare jeans is about striking the perfect balance between style, comfort, and occasion. Your choice of footwear can make or break your entire look. Let's dive into the essential considerations for impeccable shoe-flare jean coordination.

1. Consider the Occasion

The first rule of thumb is to consider the occasion. Are you dressing up for a formal event, going on a casual outing, or seeking a versatile everyday look? The choice of shoes should align with the event's formality. Opt for polished dress shoes like leather oxfords or loafers for formal occasions. For a laid-back outing, sneakers or casual boots work wonders. And for everyday comfort, consider versatile options like desert boots or chukkas.

2. Style and Silhouette Matters

Flare jeans have a distinctive silhouette, and your shoes should complement rather than clash with it. The wide-leg opening of flare jeans demands shoes that balance the proportions. Boots with a slight heel or chunky sole can provide the necessary balance and elongate your legs. Chelsea boots and wingtip shoes add a touch of sophistication, while low-top sneakers maintain a modern flair. Remember that the fit of your jeans matters, too; ensure they graze the top of your shoes without bunching up excessively.

3. Color Coordination

Color coordination is a vital aspect of any outfit, and it holds true for pairing shoes with flare jeans. While brown and black are classic choices that work well with flare jeans, don't be afraid to experiment with complementary colors. Earthy tones like tan, cognac, or chestnut pair effortlessly with denim, creating a harmonious look. For a bolder statement, consider matching your shoe color with detail in your jeans, like the stitching or a belt.

Mastering the art of pairing shoes with flare jeans is a testament to your sartorial prowess. By considering the occasion, the style and silhouette of your jeans, and color coordination, you can effortlessly create a well-balanced and stylish ensemble.

Pairing 1: Sandals

Fisherman sandals bring a touch of relaxed charm to your flare jeans ensemble. They're especially suitable for warm weather and casual occasions. The open design provides ventilation, keeping your feet comfortable on sunny days. Their versatility makes them an excellent choice for various outdoor activities.

Opt for earthy tones like brown or tan to create a harmonious look with your denim. Pair them with light wash or distressed flare jeans for a laid-back, beachy vibe. Tuck in a simple white t-shirt or a casual button-up shirt and accessorize with a woven belt to complete the easygoing aesthetic.

Fisherman sandals are ideal for beach vacations, picnics, casual outings, or leisurely walks. They exude a carefree, summery vibe and work best when you want a relaxed, beach-inspired look with your flare jeans.

Pairing 2: Espadrilles

Espadrilles blend comfort and style effortlessly, making them a fantastic option for pairing with flare jeans. These lightweight, breathable shoes are perfect for warm weather and exude a laid-back Mediterranean charm. Their versatility allows you to dress them up or down, adding a touch of casual elegance to your attire.

Opt for classic canvas espadrilles in neutral colors like navy or beige to complement your flare jeans. Pair them with a lightweight, short-sleeved linen shirt for a relaxed summer look. Roll up the cuffs of your jeans slightly to showcase the espadrilles, creating a breezy, stylish outfit.

Espadrilles are suitable for a variety of casual to semi-casual occasions. Wear them for beach vacations, brunches, outdoor parties, or when strolling through the city on a warm day. They strike the perfect balance between comfort and style, making them an excellent choice for men looking to elevate their flare jeans with a European flair.

Pairing 3: Sneakers

Canvas sneakers, whether low-top or high-top, offer a versatile and comfortable option for pairing with flare jeans. They effortlessly blend casual with a touch of urban cool, making them perfect for everyday wear. Canvas sneakers provide comfort for long days and allow you to express your personal style.

Opt for classic white or neutral-colored canvas sneakers to create a clean, timeless look with your flare jeans. Pair them with fitted or slightly flared denim for a well-proportioned appearance. Tuck in a graphic t-shirt and throw on a denim jacket for a casual, effortlessly stylish ensemble.

Canvas sneakers are suitable for various occasions, from running errands and casual outings to weekend get-togethers and music festivals. They offer a laid-back, youthful vibe and are ideal for men looking to combine comfort and style while sporting flare jeans.

Pairing 4: Loafers

Tassel and Penny loafers offer an elegant touch to your flare jeans outfit. These slip-on shoes effortlessly bridge the gap between sophistication and comfort. Loafers exude timeless style and work particularly well for semi-formal or smart-casual occasions.

Choose classic brown or black leather loafers for a refined look that complements your flare jeans. Keep the denim well-fitted, and avoid overly flared styles. Pair them with a tucked-in dress shirt and a blazer for a polished, business-casual appearance. Alternatively, opt for a crisp white shirt and a sports coat for a more relaxed yet sophisticated look.

Loafers are versatile and suitable for various events, from business meetings and semi-formal gatherings to date nights and upscale dinners. They add an air of maturity to your flare jeans outfit and are an excellent choice for men seeking an effortlessly stylish and polished appearance.

Pairing 5: Boat Shoes

Boat shoes bring a nautical and preppy vibe to your flare jeans ensemble. These comfortable and slip-on shoes are ideal for casual outings, especially during warmer seasons. Boat shoes offer both style and functionality with non-slip soles and durable construction.

Opt for classic brown or navy boat shoes to complement your flare jeans. Pair them with slightly cropped or cuffed denim to showcase the shoes. Combine with a striped or solid-color polo shirt for a classic, relaxed look. Complete the outfit with a woven belt for added flair.

Boat shoes are perfect for a range of relaxed and outdoor occasions, such as beach vacations, boat trips, picnics, and summer barbecues. They epitomize casual elegance and are an excellent choice for men looking to create a laid-back yet stylish appearance while wearing flare jeans.

Pairing 6: Driving Shoes

Driving shoes combine comfort and style, making them an excellent pairing with flare jeans. These slip-on shoes are designed for easy wear and offer a relaxed yet sophisticated look. The rubber nubs on the sole provide grip while driving, adding a unique touch to your outfit.

Opt for classic driving shoes in neutral shades like brown or navy. Pair them with well-fitted flare jeans with a slight break at the hem. Combine with a casual button-down shirt for a smart, casual appearance. For a pop of color, match your driving shoes with a coordinating belt.

Driving shoes are perfect for casual outings, weekend getaways, or date nights. They offer comfort for long drives and a refined look for various semi-casual occasions. These shoes add a touch of sophistication to your flare jeans ensemble, making them an excellent choice for men seeking style and comfort.

Pairing 7: Moccasins

Moccasins strike a perfect balance between comfort and style, making them an excellent choice for pairing with flare jeans. These slip-on shoes are known for their soft, supple leather and distinctive stitching, which adds a touch of sophistication to your ensemble. Moccasins are incredibly comfortable for long hours of wear.

Choose classic leather moccasins in neutral tones like brown or black to create a refined look with your flare jeans. Opt for well-fitted denim with a slight flare and a clean hem. Pair with a lightweight sweater or a casual button-down shirt for a polished yet relaxed appearance. Consider adding a stylish belt that complements the color of your moccasins.

Moccasins are versatile and suitable for various occasions, from casual dinners and weekend outings to business-casual meetings. They exude an air of maturity and are perfect for men looking to balance comfort and style while wearing flare jeans.

Pairing 8: Dress Shoes

Dress shoes like Wingtip Brogues, Monk Straps, Oxfords, or Derbys add a touch of sophistication and versatility to your flare jeans ensemble. They effortlessly blend classic elegance with modern style, making them an impeccable choice. Dress shoes are comfortable for extended wear and elevate your overall look.

Choose leather dress shoes in brown or black to create a sharp contrast with your flare jeans. Opt for well-fitted denim with a slight break at the hem, allowing a glimpse of your shoes. Pair them with a tailored dress shirt and a blazer for a dapper, business-casual appearance. Add a sleek leather belt matching the color of your dress shoes to complete the ensemble.

Dress shoes are perfect for formal or semi-formal occasions, including weddings, business meetings, or upscale dinners. They exude sophistication and make a powerful statement when paired with flare jeans, suitable for men seeking a refined, polished look with a touch of flair.

Pairing 9: Boots

Boots offer a rugged yet stylish edge to your flare jeans outfit. Cap-toe, Brogue, Ankle, Chelsea, Desert, Chukka, Cowboy, Military, Hiking, or Work boots provide durability and a masculine appeal. Boots are comfortable for all-day wear and can withstand various weather conditions.

Select boots that match the occasion and your personal style. Classic brown or black leather boots complement flare jeans nicely. Pair them with well-fitted jeans that allow the boots to shine. For a casual look, tuck in a flannel shirt or a denim jacket. Opt for a workwear-inspired outfit with a utility jacket and a rugged belt for a more rugged style.

Boots are versatile and can be worn for various occasions, including casual outings, outdoor activities, concerts, and even semi-formal gatherings. Their adaptability and durability make them an excellent choice for men looking to infuse their flare jeans with a rugged, masculine charm.

Pairing 10: Platform Shoes

Platform shoes bring a bold and edgy flair to your flare jeans ensemble. They offer a unique blend of height, style, and attitude. Platforms add a contemporary twist, making them an intriguing choice for fashion-forward men. These shoes provide extra cushioning and comfort for extended wear.

Opt for platform shoes with a clean and minimalist design to balance the statement they make. Classic black or white platform sneakers or boots work well with flare jeans. Pair them with fitted or slightly flared denim to maintain proportion. Complement the look with a graphic t-shirt or an oversized hoodie for a trendy, streetwear-inspired outfit.

Platform shoes are suitable for casual outings, concerts, street festivals, or creative events where you want to stand out. They make a fashion statement and add an urban edge to your flare jeans. Platform shoes are perfect for men seeking a distinctive, avant-garde look that will turn heads.

Pairing 11: Lifestyle Shoes

Lifestyle shoes, including Slip-ons, Slides, or Mules, epitomize easygoing comfort and style. These slip-on options offer convenience and a laid-back vibe that pairs perfectly with flare jeans. They're perfect for men who value both comfort and fashion.

Choose minimalist slip-ons, slides, or mules in neutral tones or muted colors to keep the focus on your jeans. Pair them with well-fitted or slightly flared denim to maintain a sleek silhouette. Consider pairing them with a relaxed, tucked-in t-shirt or a lightweight knit polo for an effortlessly stylish and comfortable look.

Lifestyle shoes are excellent for casual outings, beach trips, summer barbecues, or lounging around. They exude a relaxed charm that complements flare jeans, making them ideal for men who prioritize comfort without sacrificing style. These shoes are perfect for leisurely occasions when you want to keep it simple and comfortable.

Top Picks: Shoes to Wear with Flare Jeans

Flare jeans are making a triumphant return to the fashion scene, and choosing the right footwear can elevate your style to new heights. Here are some top shoe picks for various flare jean pairings, ensuring you look your best on any occasion.

Clarks Brixby Shore Sandal (in tan): These Fisherman sandals offer comfort and style, perfect for warm-weather casual outings. Opt for light wash, distressed flare jeans for a laid-back beach look. Ideal for beach vacations, picnics, and leisurely strolls by the water.
TOMS Alpargata Rope Espadrille (in navy canvas): These espadrilles provide comfort and a touch of Mediterranean charm. Pair with light-wash flare jeans for a relaxed summer look. Perfect for casual outings, brunches, and outdoor gatherings.
Converse Chuck Taylor All Star Low-Top Sneakers (in white): Classic and versatile, these canvas sneakers complement flare jeans effortlessly. Choose slightly flared denim for a well-balanced appearance. Great for casual outings, music festivals, and urban adventures.
G.H. Bass & Co. Larson Penny Loafer (in brown leather): Penny loafers exude sophistication and pair well with flare jeans for a smart, casual look. Opt for dark-wash flare jeans for a polished appearance. Suitable for business-casual meetings, date nights, and upscale dinners.
Sperry Authentic Original Boat Shoe (in Sahara): Boat shoes offer a casual yet stylish option for pairing with flare jeans. Combine with light-wash flare jeans for a relaxed, coastal vibe. Ideal for beach vacations, boat trips, and casual outdoor gatherings.
Cole Haan Tucker Venetian Slip-On Loafer (in British tan): Driving shoes provide both comfort and a refined appearance when paired with flare jeans. Opt for well-fitted, classic flare jeans for a sophisticated look. Suitable for casual outings, weekend getaways, and relaxed date nights.
Minnetonka Classic Moccasin (in brown suede): Moccasins offer comfort and a touch of Native American-inspired style. Pair with slightly flared denim for a casual, bohemian look. Perfect for laid-back outings, picnics, and festivals.
Cole Haan Williams Wingtip Oxford (in British tan): Wingtip brogues add sophistication and style to your flare jeans ensemble. Opt for dark-wash flare jeans for a polished, business-casual look. Suitable for formal or semi-formal events, business meetings, and upscale dinners.
Dr. Martens 1460 Combat Boot (in black): Combat boots bring a rugged and edgy element to your flare jeans outfit. Choose distressed or vintage-style flare jeans for a grunge-inspired look. Ideal for concerts, casual outings, and street festivals.
ASOS DESIGN Platform Sneakers (in black): Platform sneakers make a bold statement, adding height and urban flair to your ensemble. Pair with fitted flare jeans for a modern streetwear look. Suitable for creative events, urban adventures, and fashion-forward outings.
Vans Classic Slip-On Shoes (in checkerboard): Slip-on shoes offer ease and style, making them an excellent choice for a relaxed flare jeans look. Opt for slightly flared or wide-leg denim for a skater-inspired appearance. Perfect for casual outings, skateboarding sessions, and laid-back gatherings.

Choosing the right footwear can enhance your flare jeans ensemble and express your personal style. These top picks cover a range of options, ensuring you look your best for various occasions.

Flare jeans have made a stylish resurgence, not only among fashion enthusiasts but also among celebrities looking to embrace this iconic trend. From the red carpet to the streets, these stars have showcased their unique takes on flare jeans, proving that this vintage-inspired style is here to stay.

A$AP Rocky: showcased flare jeans with a monochromatic outfit, adding a touch of luxury with black leather Chelsea boots.
Harry Styles: rocked flare jeans paired with a fringed jacket and chunky Chelsea boots, creating a bohemian rockstar look.
John Legend: opted for a sophisticated approach, donning dark-wash flare jeans with a tailored blazer and sleek leather loafers for a classy ensemble.
Timothée Chalamet: embraced the '70s trend with light-wash flare jeans, a graphic tee, and retro sneakers, effortlessly capturing the essence of a modern-day hippie.
Brad Pitt: showcased a casual yet stylish look, combining slightly flared jeans with a classic white tee and comfortable suede desert boots for a laid-back vibe.
Zayn Malik: embraced a sleek and tailored look with dark-wash flare jeans, a fitted blazer, and classic black Oxfords, perfect for a night out.
Jared Leto: embraced maximalism, wearing bold patterned flare jeans with a vibrant jacket and platform shoes, making a statement on the red carpet.
Noah Centineo: kept it casual with distressed flare jeans, a vintage band tee, and white Converse Chuck Taylor sneakers, capturing a laid-back California style.

From rockstars to actors and musicians, celebrities confidently embrace flare jeans, each infusing their unique style and personality into the trend. Whether paired with classic loafers or edgy platform shoes, these stars are redefining how to wear flare jeans in the modern age.

Tips from Our Editors

Enhance Your Look with Accessories: Elevate the appeal of your flare jeans outfit by incorporating accessories such as belts, watches, or hats that harmonize with your pants and footwear. These subtle yet impactful elements can significantly contribute to elevating your overall style.
Give Priority to Shoe Maintenance: The condition of your shoes plays a pivotal role in how your outfit is perceived. Regularly clean and polish your shoes to maintain a fresh and impeccable appearance, free from any scuffs or blemishes. Paying attention to shoe care is essential for refining your style and leaving a lasting impression.
Properly Store Your Shoes: When your shoes are not in use, store them in a cool, dry place, away from direct sunlight. Utilize shoe trees or insert tissue paper to preserve their shape and prevent unsightly creases. These straightforward storage practices prolong the lifespan of your shoes and help them retain their pristine condition.

On a Final Note

Fashion is all about making a statement, and with the right shoes and a pair of killer flare jeans, you've just penned your style manifesto. You've embraced a timeless trend and transformed it into a distinctly masculine masterpiece.

As you step out into the world, remember that you're not just wearing clothes; you're wearing confidence, charisma, and a dash of irreverent charm. Your choice of footwear has elevated your entire look, taking it from ordinary to extraordinary. You've embraced the art of dressing, and it's evident in every confident stride you take.

So, flaunt that flair, and remember: in the grand symphony of fashion, your feet are the show-stopping crescendo. They're the exclamation point at the end of your sartorial sentence, the final brushstroke on your fashion canvas. Walk on, fashion maestro, walk on, and leave an indelible mark wherever you go.