How to Achieve the Softboy Aesthetic Style:Guide & Outfits

The fashion world is changing and there’s a popular trend that younger men are embracing and women of all ages are loving. It’s the Softboy look, a handsome blend of vintage charm and modern style. Softboy borrows touches from the relaxed 1960s scene, the hippy, anything-goes nature enjoyed in the 1970s, and the laid-back vibes of the 1990s. What a combination of comfort, nostalgia, and today’s modern lifestyles. It’s like a fashion disruption in what has always been considered masculine and macho. Softboy is all about breaking free of traditional stereotypes and allowing individual personalities to shine. This fashion frenzy opens the door to blending both traditional masculine and softer feminine apparel and accessories, creating the word Softboy. Some consider this fashion phenomenon to be a sensitivity, or a man’s emotional intelligence that is easy to recognize but difficult to define. We call it fantastic, fashion-forward, and fabulous!

The Softboy look is much more than a fashion statement. It’s like a culture shift, allowing more sensitive, thoughtful, and artistic men an outlet for expression and an inclusive sense of style. Some call it a nod to pretty boy charm or exposing your vulnerability. Sensitive boys who enjoy music, reading, and long conversations with friends about their feelings are all common among those sporting the Softboy look. So how did it start in the first place? Social Media takes center stage.

Softboy Influencers Now And Along The Way 

As with all fashion trends, pop culture plays into the picture. List celebrities like Timothee Chalamet, Jaden Smith, and popular musicians like Harry Styles, K-Pop, and BTS, as well as online influencers, were instrumental in starting and keeping this famine-energized look accepted and alive. From their longer, tousled hairstyles to colorful, comfortable, loose-fitting clothing and mixed jewelry and accessories, this chic, look is everywhere.  Social media platforms like TikTok and Instagram and the immediate viral trends they create are also paving the path for this look that continues to inspire fashion enthusiasts throughout the world. Fashion designers are also capturing this look on the runways and red carpets with dashing models dressed head-to-toe Softboy.

Softboy Fashion Is All About Personal Expression

Regardless of your age or fashion preference, men of all ages are enjoying this more casual, comfortable style. It’s not about matching and coordinated outfits. It’s all about layering favorite pieces and showcasing personal preferences. Take a look:

• Tousled Longer Hair: Let your hair down and your natural wave out to play.  Effortless waves, modern mullets and focusing on healthy hair using products that add texture and volume. A well-groomed mustache or beard is common.
• Pastel and Neutral Colors: Here’s where the fun begins. Colors that were traditionally reserved for women are now totally acceptable for men. Pastels like pink, baby blue, lavender, light green, and mint are Softboy-approved. Additionally, neutrals, including white, beige, and light gray, are common.
• Comfortable, Relaxed Pieces: The Softboy look emphasizes comfort, loose-fitting shirts, soft oversized sweaters and hoodies, sweater vests, and ultra-relaxed, baggy, high-waisted pants.
• Layering Is Key: Softboy fashion is all about layering and combining different materials like wool, cotton, denim, and others. This includes mixing different patterns and colors, like stripes with florals, checks with multi-patterns, and funky prints.
• Personalize With Accessories: The Softboy look includes wearing accessories and jewelry. Beanies, bucket hats, vintage sunglasses, and jewelry like necklaces, bracelets, watches, and rings complement this style. Functional, yet fashionable bags like leather backpacks or canvas totes work. Keep on the subtle side so as not to overdo the accessories.
• Standout Footwear: Sneakers focused on classic or retro styles are on target for the Softboy vibe. For a more polished, formal look, opt for classic loafers.

Ideas To Rock The Softboy Style Trend

The Softboy Fashion look is all about finding your confidence and comfort zone. Whether you decide to jump in all at once and go for a head-to-toe Softboy or take a more subtle approach and start slowly with a few nuances of this trend, here are a few ideas to inspire you.

Start With The Basics: Invest in basic pieces like solid t-shirts in white and pastel colors, graphic tees, oversized hoodies, sweaters, and denim jeans. A new pair of sneakers is also a foundational essential.

Find Vintage Pieces: Go to thrift stores and find vintage throwback pieces that add a unique touch to your wardrobe. This could include retro letter jackets, school band apparel, classic denim, and vintage jewelry. Not only will this allow you to create your unique look, but finding and reusing items found in a thrift store, online store or garage sale is less expensive and better for our planet. Here’s a tip: If you want to personalize your thrift find, DYI it and add graphic patches and colorful embroidery.

Experiment With Layering: Layering different pieces is key to this look and might be new territory for you. Experiment by trying different combinations and go for the look and comfort you like best. For example, wear a striped long-sleeve shirt underneath a short-sleeved graphic tee. Or pair it with a colorful graphic tee and a vintage-style longer cardigan.

Enhance With Accessories: Wear a bucket hat or beanie, a simple silver or gold chain, a vintage watch, and a pair of sunglasses to complete your look.

Select Comfortable Shoes: Shoes can make or break your Softboy vibe, so shop around for sneakers, slip-ons, or comfortable loafers. Sneaker brands like Converse, New Balance, and Vans fit well with this look. Always keep your shoes clean and tidy.

Focus on Grooming: Softboy isn’t about the 5:00 shadow. Grooming is key with your hair tousled but well maintained. A pastel highlight is totally acceptable. Pay attention to your skin care and keep it glowing. Lip balm or a touch of gloss is not out of the question.

Pictures Are Worth A Thousand Words: Outfits That Inspire Your Softer Side

Loose & Lean With Neutral Notes

This is the perfect example of how to wear a Softboy look without too much drama. Each piece from the untucked loose shirt, oversized jacket, and baggy trousers creates an easy breezy look. The white sneakers and key necklace add a charming modern touch.

It’s a Sweater Vest Vibe

The nostalgic white oversized no-collar button-down worn un-tucked is the perfect canvas for the light brown soft and sensual sweater vest. A subtle gold necklace and leather tote bag further define the fashion-forward outfit.

Light Green Demands Immediate Attention

Color your world and stand out in a crowd with this Softboy outfit designed to turn heads. Every detail from the buttoned-up button down to the soft-to-the-touch loose short ensemble is cute and charismatic. Team with a pair of throwback sneakers and ankle socks or a pair of checkered slip-ons, and you’re good to go.

Flower Power Pretty and Pulled Together

Hats off to this styling that is a touch of nostalgia and a touch of today. The hat and sunglasses get this party started but bloom with brilliance with the flower power vest and short-sleeved tee. The textured cream-colored pants add drama and design with the white sneakers balancing out the entire look. Add a chunky chain for a bit of bling.

The Shoes Have It! Checkered Shoes Check All The Softboy Boxes

Check out these checkered slip-ons that check all the boxes for this outfit. The rolled-up pants bottoms and white socks shine the spotlight on this black and white footwear. The soft and neutral sweater, white vintage collared shirt, and baggy pants check all the boxes, too.

Tousled Hair Offers Preppy Flair

The hair is key for the Softboy fashion and this guy has it figured out. A little longer with lots of fullness and just enough mess shows he takes care of his grooming business. The vintage school letter jacket and cream top and bottoms are right on point with the New Balance sneaker throwbacks. The sunglasses and single chain complete the preppy look.

Express Yourself With Softboy Style

The Softboy fashion trend is about expressing your gentler, more artistic nature through what you wear. It’s finding your balance of comfort, vintage charm, and modern appeal. Use these guidelines to inspire you to set the stage for your individuality and comfort level.