Katherine Helburn redefined women’s fashion with her confident, androgynous style, pioneering the way for women in menswear. In an era when ultra-feminine styles dominated, Hepburn boldly embraced tailored trousers, crisp button-downs, and oversized blazers, proving that comfort and elegance could coexist.
Her effortless, no-nonsense style remains just as relevant today, inspiring designers, celebrities, and fashion lovers around the world. If you want to channel Katharine Hepburn’s timeless aesthetic, this guide will show you how to master her look with fashion, hair, makeup and accessories.
Wardrobe essentials
Wide leg trousers and high-waisted pants
Hepburn made trousers a cornerstone of her style at a time when women’s pants were considered unconventional. She normalised trousers as a clothing option in high-waisted, wide-legged styles that exuded power and grace.
How to wear:
- Look for tailored, high-waisted trousers with a pleated front.
- Choose neutral colours like cream, beige, grey, navy and black for versatility.
- Pair with a fitted-blouse or tucked-in shirt to create balance.
Crisp, button-down shirts
Hepburn frequently wore crisp white, coloured, or pinstriped button-down shirts. Often oversized, they give a relaxed yet polished look.
How to wear:
- Choose a menswear-inspired, structured button-down in white or soft,muted shades.
- Roll up the sleeves for a casual, effortless touch.
- Tuck into high-waisted trousers for a perfectly balanced silhouette.
Oversized Blazers and menswear-inspired jackets
Hepburn often wore blazers that exuded power and sophistication. She frequently wore oversized, menswear-inspired pieces for an androgynous vibe.
How to wear:
- Find a slightly oversized blazer with structured shoulders.
- Opt for wool or tweed fabrics for a true vintage feel.
- Layer over a simple tee or button-down and pair with trousers or jeans.
Minimalist, no-fuss Dresses
Although Hepburn was famous for her masculine-inspired wardrobe, she also wore simple, streamlined dresses on occasion, often with clean lines and minimal embellishments.
How to wear:
- Choose A-line or shirt dresses in neutral shades.
- Avoid excessive ruffles, embellishments, or ultra-feminine details.
- Pair with a belted waist to keep the look tailored and structured.
Loafers and Minimalist Footwear
Unlike her Hollywood contemporaries, Hepburn preferred flat shoes over high heels. She would often be seen in loafers, oxfords, and simple sandals.
How to wear:
- Invest in classic leather loafers for a polished, comfortable look.
- Choose lace-up oxfords for a menswear-inspired aesthetic.
- Pair with wide-leg trousers or a tailored skirt.
Accessories and styling tips
Fedoras and felt hats
Hepburn often wore structured hats, adding a touch of Old Hollywood elegance to her looks.
How to wear it today:
- Choose felt fedoras and wide-brimmed hats in neutral shades.
- Pair with a simple trench coat or oversized blazer.
Leather belts
Hepburn’s cinched high-waisted trousers and dresses with leather belts for a refined look.
How to wear it today:
- Choose simple, structured leather belts in black or brown.
- Wear with trousers, dresses and tailored skirts to add definition to the waist.
Minimal Jewellery
Hepburn’s style was understated, so she wore very little jewellery – usually a watch, some stud earrings, or a necklace.
How to wear it today:
- Stick to gold or silver stud earrings.
- Wear a classic leather-strap watch.
- Wear single, or double strand pearl necklaces or those with small amounts of sparkle.
Hair and Makeup Guide
The Effortless Hepburn Hairstyle
Hepburn kept her hair natural and fuss-free, often styling it in soft waves or a simple updo.
How to get Hepburn’s Hair Look:
- For soft waves, use a large curling iron and brush through for a natural finish.
- For a classic updo, twist your hair into a low-bun or chignon.
- Avoid using excessive styling products, Katharine Hepburn’s hair had a more effortless feel.
Fresh, matte and natural skin
Hepburn’s complexion always looked healthy, matte, and natural, avoiding the heavily powdered look that was common in 1940s Hollywood. She favored a fresh, no-fuss appearance with a focus on even skin tone and a natural glow.
How to get Hepburn’s skin:
- Matte but not flat: Use a lightweight matte foundation or a soft-focus tinted moisturiser to even out your skin tone without making it look heavy.
- Apply a small amount of peach or soft rose blush to the apples of your cheeks for a healthy, subtle flush.
- Hepburn didn’t follow modern contouring trends – her beauty was effortlessly structured due to her high cheekbones and defined jawline. Instead of contour, use a hint of bronzer for warmth.
- Lightly dust translucent powder over the T-zone to keep the complexion fresh and matte, just like Hepburn.
Natural and Defined Eyes
Katharine Hepburn’s eyes were always subtly enhanced, with natural brows, soft definition, and no heavy eyeliner or false eyelashes.
How to get Hepburn’s eyes:
- Apply a neutral, taupe, or soft brown shadow in the crease for natural depth. Avoid shimmery or dramatic colour.
- Unlike her contemporaries who wore thick cat-eye liner, Hepburn’s eye makeup was softer. If using eyeliner, choose brown or soft black eyeliner and apply it lightly along the upper lash line, smudging it out for a natural effect.
- Curl lashes and apply one or two coats of brown or black mascara to subtly enhance your eyes without making them look overly dramatic.
- Hepburn’s eyebrows were full, slightly arched and natural-looking. Instead of over-plucking, she brushed them up and kept them full. Use a brow pencil or powder to lightly fill in any sparse areas while keeping the shape soft and natural.
Soft, muted and understated lips
Unlike the bold, red lips of the 1940s, Hepburn’s lip colour was subtle and chic, often in natural, muted tones.
Get Katharine Hepburn’s lips:
- Hepburn often wore brick-red, muted rose, or soft-brown lipsticks, rather than bright reds and scarlets that were popular during the 1940s.
- Choose a matte or satin finish. Her lips always looked natural, not overly glossy or shiny.
- Apply lipstick with your fingertips and blot with a tissue for a soft, lived-in look rather than a precise, painted effect.
- Use a lip liner in a matching shade to enhance your natural lip shape, avoiding overdrawn or exaggerated lines.
Katharine Hepburn’s style wasn’t just about clothing – it was about attitude. She embodied confidence, independence, and a refusal to conform to societal expectations.
Her wardrobe was built on strong tailoring, simple elegance, and timeless menswear influence. By embracing wide-leg trousers, crisp shirts, and structured blazers, you can channel Hepburn’s effortlessly chic aesthetic.
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