How to Style Penny Loafers Jordan Obrien: How to Style

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Penny loafers, those iconic slip-on shoes, have a rich history and a timeless appeal. They’ve graced the feet of everyone from preppy college students to Hollywood icons, and their versatility is undeniable. But with so many styling options, how do you make them work for you? Fear not! This guide, inspired by the fashion sensibilities of Jordan O’Brien, will break down everything you need to know about styling penny loafers, ensuring you look effortlessly chic every time.

We’ll explore different outfit combinations, from casual weekend looks to more polished ensembles suitable for the office or a night out. We’ll delve into the nuances of choosing the right materials, colors, and accessories to complement your penny loafers and personal style. Get ready to elevate your shoe game and discover the endless possibilities that these classic shoes offer!

The Anatomy of a Penny Loafer

Before we dive into styling, let’s understand the key features of a penny loafer. This knowledge will help you make informed decisions when choosing the right pair and coordinating them with your outfits.

Key Components:

  • The Upper: This is the main part of the shoe, typically made from leather, suede, or other materials. The quality of the upper significantly impacts the shoe’s durability and appearance.
  • The Penny Strap: This distinctive leather strap, running across the vamp (the top of the foot), is the defining feature. It often features a slit, originally designed to hold a penny.
  • The Sole: Soles can vary from leather to rubber, each offering different levels of comfort and traction. Leather soles are traditional and elegant, while rubber soles offer better grip and weather resistance.
  • The Heel: Penny loafers usually have a low, stacked heel, adding a touch of sophistication without sacrificing comfort.

Materials Matter:

The material of your penny loafers influences their style and the occasions for which they’re best suited:

  • Leather: Leather penny loafers are a classic choice, offering a polished look. They are versatile and can be dressed up or down. Consider full-grain leather for durability and a premium feel.
  • Suede: Suede penny loafers have a more casual, relaxed vibe. They’re great for adding texture to an outfit but require more care to protect them from the elements.
  • Patent Leather: Patent leather penny loafers are a bold choice, perfect for adding a touch of glamour to your evening attire.
  • Other Materials: You might find penny loafers made from canvas, synthetic materials, or even exotic leathers. These offer unique style options but may not be as versatile or durable.

Choosing the Right Penny Loafers

With so many options, selecting the perfect pair of penny loafers can seem daunting. Here’s a guide to help you make the right choice, considering factors like fit, color, and style.

Fit Is Paramount:

A well-fitting penny loafer is essential for comfort and style. Here are some tips: (See Also: How to Style Driver Loafers: A Comprehensive Guide)

  • Length: Your toes should not be cramped, and there should be a small space (about a thumb’s width) between your longest toe and the end of the shoe.
  • Width: The shoe should fit snugly around your foot without feeling overly tight.
  • Heel: The heel should not slip excessively when you walk.
  • Break-in Period: Leather penny loafers often require a break-in period. Wear them around the house for short periods to allow the leather to soften and mold to your feet.

Color Considerations:

The color of your penny loafers significantly impacts their versatility:

  • Black: Black penny loafers are a staple, suitable for both formal and casual occasions. They pair well with almost anything.
  • Brown: Brown penny loafers are incredibly versatile. Lighter shades of brown (like tan or cognac) are perfect for a relaxed, casual look, while darker browns can be dressed up.
  • Burgundy/Oxblood: These rich colors add a touch of sophistication and work well with both neutral and bolder colors.
  • Other Colors: Consider navy, green, or even bolder colors like red or yellow for a statement look. These are best suited for more casual outfits.

Style Variations:

Penny loafers come in various styles. Consider these:

  • Classic Penny Loafer: This is the traditional style, with a leather upper, penny strap, and low heel.
  • Tassel Loafer: While not a penny loafer, they share similar characteristics. Tassel loafers feature tassels on the vamp, adding a touch of flair.
  • Bit Loafer: These loafers have a metal bit across the vamp, often associated with Gucci. They have a more refined and luxurious appearance.
  • Driving Loafer: Designed for driving, these loafers often have a rubber sole that extends up the heel for better grip and comfort.

Styling Penny Loafers: Outfit Ideas Inspired by Jordan O’brien

Now, let’s get to the fun part: styling your penny loafers! Here are some outfit ideas inspired by Jordan O’Brien’s sophisticated and effortless style.

Casual Chic: Weekend Outfits

  • The Classic Combination: Pair brown leather penny loafers with dark wash jeans (straight or slim fit) and a crisp white Oxford shirt. Add a navy blazer for a touch of polish.
  • The Relaxed Look: Wear suede penny loafers in a neutral color (like beige or grey) with chinos and a simple t-shirt or a knitted polo shirt. Roll up the cuffs of your chinos for a more casual vibe.
  • The Layered Approach: Combine penny loafers with corduroy pants, a flannel shirt, and a bomber jacket. This outfit is perfect for cooler days.
  • The Summer Staple: Opt for lighter-colored penny loafers (tan or light brown) with linen shorts and a short-sleeved button-down shirt.

Smart Casual: Office-Ready Looks

  • The Business Casual Essential: Wear black or dark brown penny loafers with tailored trousers (chinos or dress pants) and a button-down shirt. A lightweight sweater or a blazer can complete the look.
  • The Elevated Casual: Combine penny loafers with a well-fitting polo shirt, tailored chinos, and a sport coat.
  • The Versatile Choice: Pair your penny loafers with a dark-colored suit (navy or charcoal) and a button-down shirt. This is a great alternative to dress shoes for a more relaxed yet professional appearance.
  • The Statement Piece: Wear a bold-colored penny loafer (burgundy or oxblood) with a neutral-colored suit (grey or beige) and a patterned shirt.

Elevated Evening: Night Out Outfits

  • The Sophisticated Look: Pair black patent leather penny loafers with a well-fitted tuxedo or a dark suit. A crisp white shirt and a bow tie will complete the ensemble.
  • The Smart Evening: Combine dark brown or burgundy penny loafers with a velvet blazer, dark wash jeans, and a dress shirt.
  • The Modern Classic: Wear penny loafers with tailored trousers, a silk shirt, and a stylish overcoat.
  • The Bold Choice: Wear a pair of penny loafers with a patterned suit and a statement shirt.

Accessorizing Your Penny Loafer Outfits

Accessories can elevate any outfit. Here’s how to incorporate them into your penny loafer looks.

Socks: The Understated Detail

  • No-Show Socks: For a clean, minimalist look, especially in warmer weather, use no-show socks.
  • Dress Socks: Choose dress socks that complement your outfit. Solid colors are always a safe bet, but you can also experiment with patterns (stripes, argyle) for a touch of personality. Match the color of your socks to your pants or to a color in your shirt.
  • Casual Socks: For a more relaxed vibe, try thicker socks in a contrasting color.

Belts: The Finishing Touch

  • Match Your Leather: Ideally, your belt should match the color and material of your penny loafers.
  • Consider the Buckle: Choose a belt buckle that complements the overall style of your outfit. A simple, understated buckle is generally a good choice.

Watches and Jewelry: Personalizing Your Style

  • Watches: A classic watch adds a touch of sophistication. Choose a watch with a leather strap that complements your penny loafers.
  • Jewelry: Keep it simple. A subtle bracelet or a ring can add a touch of personality without overpowering your look.

Caring for Your Penny Loafers

Proper care will extend the life of your penny loafers and keep them looking their best. (See Also: How to Shine Alden Calf Loafers: A Comprehensive Guide)

Cleaning and Maintenance:

  • Leather: Clean leather penny loafers regularly with a leather cleaner and conditioner. Apply a leather protector to shield them from the elements.
  • Suede: Use a suede brush to remove dirt and debris. Protect suede with a suede protector spray.
  • Storage: Store your penny loafers in a cool, dry place. Use shoe trees to maintain their shape.
  • Rotation: Rotate your shoes to allow them to air out and prevent wear and tear.

Repair and Restoration:

  • Heel and Sole Repair: Take your penny loafers to a cobbler for heel and sole repairs.
  • Leather Restoration: A cobbler can also repair scratches and scuffs on leather shoes.

Penny Loafer Don’ts: Common Styling Mistakes to Avoid

While penny loafers are versatile, some styling choices can detract from their appeal. Here’s what to avoid:

  • Wearing Penny Loafers with Athletic Socks: This is a major style faux pas. Always choose dress socks or no-show socks.
  • Pairing Penny Loafers with Overly Baggy Clothing: Penny loafers look best with well-fitting clothes. Avoid excessively loose or oversized garments.
  • Wearing Damaged or Worn-Out Penny Loafers: Invest in proper care and maintenance to keep your penny loafers in good condition.
  • Ignoring the Occasion: While versatile, penny loafers aren’t suitable for every occasion. Avoid wearing them to extremely formal events or athletic activities.

Penny Loafers and the Seasons

Penny loafers can be worn year-round, but you might adjust your styling based on the weather.

Spring and Summer:

  • Lighter Colors: Opt for lighter-colored penny loafers (tan, light brown, navy) and pair them with lighter fabrics like linen and cotton.
  • Shorts: Penny loafers look great with shorts. Choose tailored shorts for a more polished look.
  • No-Show Socks: Keep your ankles cool and your look streamlined with no-show socks.

Fall and Winter:

  • Darker Colors: Embrace darker-colored penny loafers (black, brown, burgundy) and pair them with heavier fabrics like wool and corduroy.
  • Layering: Layer your outfits to stay warm. A blazer, a sweater, or a coat can complete your look.
  • Socks: Choose thicker socks for warmth and style. Experiment with patterned socks.

Penny Loafers: A Style Evolution

Penny loafers have evolved over time, reflecting changes in fashion and culture. From their origins as practical footwear for college students, they’ve become a symbol of timeless style. They’ve been embraced by various subcultures, from preppy to mod, and continue to be a staple in modern wardrobes.

Historical Context:

  • Early 20th Century: The penny loafer’s roots are in the early 20th century with the Norwegian loafer.
  • Mid-20th Century: The penny loafer gained popularity in the United States, particularly among college students. The penny strap was added for practicality.
  • The 1950s and 1960s: Penny loafers became a symbol of preppy style and were widely adopted by Ivy League students.
  • Modern Era: Penny loafers continue to be a style staple, with various designers and brands offering different interpretations of the classic shoe.

Penny Loafers and Body Types

Penny loafers can be flattering for different body types. Here’s how to style them:

For Slim Builds:

  • Slim-fit pants: Choose slim-fit or straight-leg pants to complement your frame.
  • Layering: Layer your outfits with a blazer or a cardigan to add visual bulk.
  • Avoid Oversized Garments: Avoid overly large clothing, as it can overwhelm your figure.

For Athletic Builds:

  • Tailored Fit: Opt for tailored clothing that fits well without being too tight.
  • Avoid Skinny Jeans: Skinny jeans can make your legs look even more muscular.
  • Consider Chinos or Dress Pants: These can be great options for a balanced look.

For Larger Builds:

  • Well-Fitted Clothing: Choose well-fitted clothing that flatters your figure.
  • Darker Colors: Darker colors can be more slimming.
  • Vertical Lines: Opt for clothing with vertical lines to create a slimming effect.

Penny Loafers: The Investment Piece

Investing in a quality pair of penny loafers is a worthwhile decision. They are a classic, versatile, and durable shoe that can elevate any wardrobe. (See Also: Are Loafers Cold Winter? A Guide to Staying Stylish & Warm)

Quality Matters:

  • Leather Quality: Choose penny loafers made from high-quality leather for durability and longevity.
  • Construction: Look for well-constructed shoes with durable soles and stitching.
  • Brand Reputation: Research different brands to find those known for producing high-quality penny loafers.

Cost Per Wear:

  • Longevity: High-quality penny loafers can last for many years with proper care.
  • Versatility: Their versatility means you can wear them with a wide range of outfits.
  • Cost-Effectiveness: Over time, the cost per wear of a quality pair of penny loafers is often lower than that of cheaper, less durable shoes.

Penny Loafers: A Final Word

Penny loafers are more than just shoes; they’re a statement. They embody a sense of timeless style, sophistication, and versatility. By understanding the nuances of fit, color, and styling, you can confidently incorporate penny loafers into your wardrobe and express your personal style.

Jordan O’brien’s Influence:

Jordan O’Brien’s keen eye for classic style and attention to detail serves as a perfect inspiration for embracing the penny loafer. Her approach focuses on simplicity, quality, and timelessness, making the penny loafer a key element in a well-curated wardrobe.

Verdict

Styling penny loafers, as we’ve seen, is a delightful journey of personal expression. From casual weekends to formal evenings, these shoes provide a foundation for countless stylish ensembles. Remember to consider the materials, colors, and accessories to create looks that truly reflect your personality. Embrace the versatility of penny loafers, and you’ll find yourself reaching for them time and time again. With the right pair and a little inspiration, you can effortlessly incorporate this timeless classic into your everyday wardrobe and experience the enduring appeal of the penny loafer. Happy styling!

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