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How to Style Leather & Pinstripes for an Effortless Look

Styling leather jacket and pinstripes

As winter lingers, layering has become more like a chore than a cozy embrace. Don’t get me wrong—I love a good cold-weather look, but I’m officially counting down to summer. Until then, I’m making the most of structured, textured outfits that balance warmth and style. This week’s favorite fit? I styled leather and pinstripes – A perfect mix of vintage edge, effortless tailoring, and understated drama.

The Breakdown: A Chic, Monochrome Winter Look

1. The Leather Jacket – Vintage Cool

A black leather jacket is always a staple, but the magic is in the fit. This oversized beauty drapes just right, giving that relaxed, “I just threw this on” vibe while still feeling put together. It’s the kind of piece that instantly elevates any outfit—whether over casual denim or, in this case, sharp pinstripes.

2. The Pinstriped Trousers – A Touch of Tailoring

Pinstripes are timeless, and these trousers add just the right amount of contrast to the look. The soft, wide-leg cut brings a sense of ease, balancing out the structured leather. They move with me, creating that effortless flow that makes an outfit feel intentional without trying too hard.

3. The Boots – Subtle but Sharp

Footwear is where personality shines, and these pointed-toe boots quietly steal the show. The deep brown, textured leather adds a rich detail that keeps the monochrome look from feeling too flat. The heel? Just enough to elongate the legs while keeping things comfortable for city strolling.

4. The Bag – Small but Mighty

A structured shoulder bag is my go-to for polished minimalism. The dark shade blends seamlessly into the look, while the shape adds that refined touch. It’s functional, stylish, and the perfect final detail.

5. Hair & Makeup – The Finishing Touch

Nothing complements an all-black outfit like voluminous, natural hair and a glowing, understated makeup look. A soft, glossy lip and a bit of highlight keep things fresh, proving that effortless style isn’t just about the clothes—it’s about the whole energy.

Why This Look Works

This fit is proof that winter dressing doesn’t have to feel heavy or repetitive. It’s about finding that perfect mix of structure and softness, edge and ease. Now, if only we could fast-forward to warmer days…

What’s your go-to winter outfit when you’re over layering but still need to keep warm? Let me know in the comments!

Outfit Details

Leather Jacket – Thrifted

Pants – Addax

Boots & Bag – Thrifted

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