How to Dress Like a Softboy: The Ultimate Guide to Softboy Outfits

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Do you admire the effortlessly cool and relaxed style of the softboys? Are you wondering how to pull off this laid-back aesthetic?

Don’t worry; I’ve got you covered! From understanding the softboy aesthetic to essential wardrobe pieces and accessorizing tips, I’ll show you how to dress like a softboy and nail the look.

Understanding the Softboy Aesthetic

The softboy aesthetic is a fashion trend that has been gaining popularity in recent years. It is all about embracing a relaxed and casual style that exudes confidence and comfort.

This style is made up of a combination of vintage and modern pieces, with an emphasis on oversized and loose-fitting garments. A softboy outfit is all about balance, being neither too dressy nor too casual.

But the softboy aesthetic is more than just a fashion trend. It’s a lifestyle that embraces comfort and simplicity in all aspects of life. Softboys often have a laid-back and carefree attitude, and they prioritize their mental and emotional well-being over material possessions and societal expectations.

softboy outfit
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What is a Softboy?

A softboy is a person who embraces a relaxed and casual style that is often inspired by vintage garments. They usually wear loose-fitting clothes and oversized pieces and have a preference for muted colors, neutral tones, earthy hues, and textured fabrics such as cotton, wool, and denim.

Softboys tend to embrace a more laid-back and minimalist approach to fashion, with few statement pieces in their wardrobe.

Softboy vs. Eboy: What’s the Difference?

The eboy and softboy aesthetics can be confusing to differentiate. While both styles are inspired by vintage garments, the softboy style tends to be more understated and minimalist, while the eboy style can be more flamboyant and daring.

Softboys tend to lean towards muted colors, while eboys prefer bright, neon colors. Both styles, however, embrace free and easy comfort, prioritizing comfort over fashion.

Essential Softboy Wardrobe Pieces

Now that you understand the softboy aesthetic, let’s take a closer look at the essential wardrobe pieces for dressing like a softboy.

Oversized Sweaters and Hoodies

The oversized sweater and hoodie are the foundation of the softboy wardrobe. These articles of clothing are comfortable, cozy, and easy to wear.

The trick is to embrace a size or two up for that slouchy oversized look that softboys love. Pair them with your favorite high-waisted trousers and sneakers for a cool and relaxed look.

softboy oversized
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Vintage Graphic Tees

Vintage graphic tees are another staple in the softboy wardrobe. Softboys often prefer tees with muted tones and slightly faded graphics, giving them a worn-in, vintage look.

A key to this style is to not be overly fussy about the fit – embrace a slightly too-large graphic tee that can be tucked or cropped to achieve a casual yet stylish look.

High-Waisted Jeans and Trousers

The high-waisted jeans and trousers are must-haves in any softboy wardrobe. These pieces create clean and simple lines and perfectly complement the oversized sweater and hoodie.

Cozy Cardigans

A cozy cardigan is a classic piece in the softboy wardrobe. This comfortable layering piece adds texture and warmth to any outfit and can be worn with anything from graphic tees to button-ups.

Softboys often embrace chunkier knits in muted tones for a truly comfortable look.

Statement Socks and Accessories

Softboys love statement socks and accessories to add a subtle pop of color and personality to their outfits. They can easily be worn with classic sneakers to add an extra twist to the look.

Adding unique jewelry, such as pins and necklaces, is also a great way to add character to an outfit. Don’t be afraid to experiment and mix and match different accessories.

softboy accessories
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Layering and Combining Softboy Outfits

One of the biggest appeals of the softboy wardrobe is the ease with which it can be layered and combined. Here are some tips on how to nail the art of layering and combining softboy outfits.

Mastering the Art of Layering

Softboys love the art of layering. During cooler weather, it’s about layering cozy knit cardigans over graphic tees or underneath oversized jackets.

Try layering a denim jacket over a lighter shirt with cuffed sleeves for warmer weather. The variety of clothing textures and weights is used to enhance a look and make each individual piece stand out in its own right.

Mixing Patterns and Textures

Talking of textures! Softboy fashion also focuses on the play of different textures. Chambray shirts, wooly socks, and denim jackets can be combined in harmonious contrasts to create a complex texture experience.

To master this technique, choose similar tones and complement them with a plaid scarf/tie, creating a soft, understated look that still complements one’s look.

Balancing Casual and Dressy Elements

The day-to-day softboy look is generally casual; however, it’s easy to dress it up a bit. A plain white shirt and denim jacket can be paired with a pair of black trousers, creating a serious silhouette while remaining comfy and understated.

It’s all about finding a balance with one’s style that makes them feel comfortable and confident.

Accessorizing Your Softboy Look

The final touches of a softboy outfit can be found in the accessories. Layering these subtle touches adds a final layer of personality to any look.

Choosing the Right Footwear

Footwear completes any look, and the softboy shoe choice can range from a grungier high-top sneaker to sleeker, minimalist-looking shoes.

Go for quality and comfort over flashiness to get the look spot on. Classic skate shoes or Converses complement a look, keeping the outfit understated even with the added design elements.

softboy shoes
Credit: @INTOHYPEZONE, Pinterest

Hats, Beanies, and Headwear

Headwear can offer the perfect accent to any outfit. Softboys love to add a touch of personality, either through subtle branded caps or even a Jackie Onassis hat.

Beanies look great when contrasted with oversized sweaters, while bucket hats and well-worn poolside add versatility to an outfit.

Bags and Backpacks

Carrying a simple, quality, and understated bag or backpack is a must-do accessory. A quality leather backpack or a classic white canvas tote bag can also add a subtle touch of personality to any outfit.

The key to softboy accessories is function over form; these bags need to be practical while keeping to the minimalist ideal.

Jewelry and Pins

Jewelry and pins are the perfect way to add a subtle touch of personality without overwhelming any given look. Softboys will often wear a unique piece of jewelry, such as a pendant or a unisex watch, and pins are a great way to liven up clothing while still keeping it simple and understated.

Overall, dressing like a softboy is all about following a few key principles that prioritize comfort, simplicity, and balance. Essential pieces such as oversized sweaters, hoodies, and vintage graphic tees each bring something special to the equation.

Michael (Mike) Davis is an experienced writer and freelance stylist specializing in men's grooming, skincare, hairstyles, and fashion.

With over 5 years of industry experience, he has a deep understanding of men's skin types, hair textures, and fashion preferences. Mike's passion for staying up-to-date on the latest trends and techniques is evident in his writing, which has been featured in popular publications.

He takes pride in providing practical advice to his clients and readers.

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