How to Dress Boyish – 3 Outfits for a Masculine Vibe Look

Weekly Newsletter

Keep up with the latest in fashion, beauty and style!

Boyish style is a way of dressing in men’s clothing, like tailored trousers, button-up shirts, structured blazers, and utilitarian jackets, depicting a practical masculine look.

A Typical Boyish Outfit
A Typical Boyish Outfit

Compared to the more casual look of the Tomboy style, Boyish comprises structured and tailored menswear garments in clean and fitted lines, such as blazers, trousers, and button-up shirts, to create a polished look while maintaining a masculine edge.

Boyish style

Nowadays popular in Asia, the boyish look is credited to early 90s celebrities like Marlene Dietrich and Katharine Hepburn as the first women to wear masculine clothing and challenge traditional gender norms.

Marlene Dietrich and Katharine Hepburn's Boyish Style
Marlene Dietrich and Katharine Hepburn’s Boyish Style

In this article, I’ll introduce you to 3 Boyish style outfits curated by our stylists for their power to depict a masculine look.

1. Boyish Academia

Boyish Academia fashion style outfit

Women's White Solid Color Drop Shoulder Shirt With Curved Hem For Workwear Vintage Straight High Waist Jeans With Distressed Details Retro Crossbody Bag With Large Capacity  Business Formal Pu Leather Shoes
Men Minimalist Solid Suspender For Daily Life Zipper Free-Tying Striped Necktie Suitable For Shirts, Daily Wear & Gifting Solid Crew Socks

Start this Boyish Academia outfit with a crisp white Oxford shirt from Brooks Brothers, a brand synonymous with classic tailoring.

Match it with high-waisted, wide-leg dark denim jeans from Levi’s, brown leather suspenders from Fossil for a vintage dark academic touch, and a Ralph Lauren Preppy rep tie with a traditional striped pattern.

Billie Eilish in oversized oxford shirt and tie

Accompany with a brown messenger bag from Coach and Clarks’ brown leather lace-up shoes with simple white crew socks, for a timeless masculine aesthetic rooted in the classic preppy style.

Gigi Hadid and Emma Stone in Suspenders

2. Boyish Skater

Boyish Skater fashion style outfit

V Neck Drop Shoulder Oversized Sweater Solid Round Neck Tee High Waist Ripped Mom Jeans adidas Originals Forum mid trainers in triple white
Women's Warm Knit Hat With Fleece Lining Women's Mid-calf Socks, Ins Style Hip Hop Minimalist Chain Bracelet And Necklace, Stainless Steel Chain Jewelry Set Pairs of Hoop Earrings 316L Stainless steel Earrings Set Tiny Huggie Hoop Earrings

Start your Boyish Skater outfit with a quality white T-shirt from Hanes or Gildan, layered with a dark brown V-neck sweater from Uniqlo.

Bella Hadid and Hailey Bieber in v-neck sweater

Complement them with light-washed, ripped, straight-leg Levi’s jeans for a rugged skater feel, Adidas Pro Model ADV skate sneakers for a touch of streetwear, and a dark brown argyle pattern from Happy Socks.

Kendall Jenner and Zendaya in ripped boyfriend jeans

Complete the look with a Carhartt mustard ribbed knit beanie for a pop of color against the neutral tones and small hoop earrings from Madewell for a streetwear boyish skater look.

3. Boyish Grunge

Boyish Grunge fashion style outfit

Brown Woven Hooded Shirt Solid Rolled Short Sleeve Tee
Frenchy High Waist Wide Leg Pants Women's Coffee Brown Faux Rabbit Fur Aviator Hat With Large Head Circumference, Fashionable Windproof Cap
White Coated Oval-shaped Fashionable Women's Eyeglasses Women's Silver Buckle Pu Waist Belt Converse Chuck Taylor All Star Hi unisex trainers in black

Create the Boyish Grunge look with a loose-fitting white T-shirt from American Apparel or H&M, ideal for affordable basics, an oversized flannel shirt from Patagonia, and loose-fitting khaki chinos from Dickies.

Kendall Jenner and Chrissy Teigen in oversized flannel shirt

Accessorize with Christian Roth 6558 series white sunglasses, a pair popularized by Curt Cobain, and a Carhartt lumberjack hat – both grunge-style essentials.

Kim Kardashian and Cheryl Cole in trapper hats

Complete with a sturdy black leather belt from Levi’s, argyle pattern socks in dark brown peeking above the shoes, and Converse Chuck Taylor All-Star 70 for a relaxed boyish grunge feel.

Similar Styles to Boyish

Tomboy | Androgynous | Agender | Teddy Girl | Skater | Grunge | Light Academia | Dark Academia

Weekly Newsletter

Keep up with the latest in fashion, beauty and style!

Style Like a Pro!

Are you looking to improve your fashion style and unsure where to start?

Contact The VOU’s style experts to receive your free and personalized styling advice based on your current way of dressing, preferred outfits, colors, aesthetics, age, gender, body shape, location, and event you seek to attend.

A passionate advocate for inclusivity and diversity, Aidan is the driving force behind The VOU magazine as its Editorial Manager. With a unique blend of editorial acumen and project management prowess, Aidan's insightful articles have graced the pages of The Verge, WWD, Forbes, and WTVOX, reflecting his deep interest in the dynamic intersection of media and technology.

Similar Articles


Please enter your comment!
Please enter your name here

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.