Leather leggings are a classic piece of clothing that look good and feel good.
When put together with care, they make outfits that look classic and classy.
They look effortlessly classy when worn with classic pieces like tailored blazers, soft knits, or structured coats.
With the right layers, textures, and accessories, they can get a “old money” look that is polished, understated, and sure of themselves.
Leather leggings are versatile and stylish, and they can be worn for walks in the city, casual events, or more formal occasions. It’s easy to style them this way.
13 Old Money Outfits With Leather Leggings To Look Timeless
Timeless Elegance With Leather Leggings
This outfit blends luxury with simplicity. The classic camel coat drapes effortlessly over a silk blouse and sleek leather leggings, delivering refined sophistication.
Accessories, like the statement pearl necklace and structured handbag, add an “old money” touch to the look. Black stilettos complete the outfit with clean lines and confidence.
The ensemble speaks volumes without trying too hard — polished, timeless, and chic. Perfect for transitional seasons or an upscale event, it’s a masterclass in understated elegance.
Effortless Sophistication With Burgundy Leather Leggings
Pairing a cream turtleneck sweater with burgundy leather leggings adds texture and elegance. Draping a camel blazer over the shoulders adds structure, and gold hoops add a subtle edge.
Loafers finish off the look with a classic, timeless look. This outfit is perfect for a day out or a casual meeting because it’s comfortable, stylish, and practical or a day out or a casual meeting.
It’s practical, luxurious, and calm — a classic take on modern style with effortless charm.
Polished Comfort With Equestrian-Inspired Leather Look
This outfit is a great mix of structure and casual charm. A crisp navy blazer looks great with a striped button-down shirt, giving you a sophisticated look.
Adding a practical, equestrian touch with leather leggings and tall riding boots makes it both stylish and useful. Warmth is added by the burnt orange crossbody bag, which balances out the cool tones.
This outfit is great for both casual walks outside and dressy events during the day. It’s classy but easy to wear, with a classic style that makes you feel both sure of yourself and grounded.
Subtle Sophistication With Olive Leather Leggings
This outfit is a mix of modern style and soft elegance. When paired with a silk camisole, the olive leather leggings add a unique but understated twist.
A cropped jacket with texture adds polish and goes well with a clean silhouette. Matching flats keep you comfortable without giving up style.
A pair of delicate earrings with a hint of shine finishes off the look. This outfit is sophisticated and easygoing, making it perfect for a relaxing afternoon or a casual get-together with friends.
It looks classic, calm, and put together without much effort.
Refined Layers With Chocolate Leather Leggings
This outfit gives off a subtle air of sophistication. When worn with a crisp white blouse, the chocolate brown leather leggings make a rich, textured base.
A long, tailored gray vest gives the outfit structure and a more polished look.
Simple flats and a metallic clutch finish off the outfit, making it completely practical without sacrificing style.
It’s timeless, polished, and calm, making it perfect for offices or more formal daytime settings.
This style strikes a balance between comfort and style, giving you confidence with its clean lines and understated luxury.
Classic Elegance With Riding-Inspired Leather Leggings
Putting on black riding leggings and tall boots gives this outfit a horsey vibe. The tailored navy coat adds structure, and the soft cream scarf adds warmth and contrast.
Simple accessories, like a sleek wristwatch, finish off the polished look without much effort.
This outfit is great for strolls in formal settings or on crisp outdoor days because it’s the perfect mix of comfort and refinement.
Bold Elegance With Velvet and Leather Pairing
This outfit is a mix of confidence and style. The rich emerald velvet blazer looks great with the sleek black leather leggings that add texture and depth.
A tight black turtleneck keeps the base clean, and sharp black boots give it a sophisticated edge.
The structured brown bag balances out the darker colors and is useful without being too much of a distraction.
This outfit is both bold and put-together, making it great for walks in the city or fancy evenings out.
It’s modern, strong, and striking without trying too hard. It’s a great example of understated sophistication.
Timeless Monochrome With Taupe Leather Leggings
This set combines classic tones with more up-to-date styles. The taupe leather leggings have a sleek look that goes well with the silk blouse with the soft bow detail.
An overcoat in cream adds class and balances out the tailored shape.
The handbag with pearls adds texture, and the matching heels finish off the sophisticated look.
This outfit is great for walking around the city or going on a fancy day trip. It’s polished, understated, and confident without trying too hard.
This shows that neutral colors can make a statement without being too loud.
Relaxed Luxury With Chocolate Leather Leggings
This outfit defines laid-back refinement. The oversized cream sweater brings comfort and balance to the structured chocolate leather leggings.
Suede loafers offer casual ease, while the bold gold chain necklace elevates the ensemble with an elegant touch.
A slouchy suede bag complements the earthy palette, keeping the look cohesive and practical.
Perfect for cozy afternoons or quiet moments at home, this style blends comfort and sophistication effortlessly. It’s timeless, relaxed, and confidently understated.
Modern Power Dressing With Leather and Blazer
This outfit combines sharp tailoring with sleek details. Black leather leggings anchor the look with structure, paired with a crisp white shirt for balance.
The oversized camel blazer adds a confident, modern edge, while chunky loafers and gold accessories keep it polished. A small black handbag ties the ensemble together without distraction.
Ideal for elevated daywear or sophisticated evening events, this style blends strength and refinement. It’s versatile, poised, and exudes calm confidence.
Polished Sophistication With Cream Blazer Look
This outfit strikes the perfect balance. The tailored cream blazer adds structure, bringing a refined silhouette that exudes timeless elegance. Sleek navy leather leggings provide contrast, enhancing the outfit’s modern appeal.
A silk scarf tied at the neck introduces subtle color and detail, while statement earrings complete the polished ensemble.
Perfect for formal outings or sophisticated daytime affairs, this look feels intentional and confident. It blends classic tailoring with a modern touch, proving that less is often more.
Nautical Elegance With Burgundy Leather Leggings
This outfit blends coastal charm with effortless polish. Burgundy leather leggings add modern flair, paired with a striped button-down for a classic touch.
A light gray sweater tied over the shoulders keeps it relaxed and practical. Burgundy loafers and a tan leather tote complete the look, adding functionality and balance.
Ideal for a day on the water or seaside strolls, this style feels intentional and refined. It’s understated luxury with a nautical influence that remains timeless and versatile.
Effortless Sophistication With Taupe Leather Leggings
This outfit combines structure with contemporary elegance. Taupe leather leggings create a streamlined base, paired with a fitted black top for contrast.
The long camel trench adds movement and refinement, while pointed heels match the leggings for a polished finish.
A pearl choker introduces a classic detail, elevating the ensemble with understated luxury.
Perfect for gallery visits or chic events, this look feels confident and intentional. It’s modern, and poised, and strikes the perfect balance between edge and sophistication.
Timeless Layers With Olive Leather Leggings
This outfit has elements of both old and new styles. A crisp white shirt looks great with olive leather leggings that make the base look clean and put together.
A tailored houndstooth blazer worn over the shoulders gives the outfit shape and a classic look.
A silk scarf and gold bangles add subtle texture and sophistication to the outfit.
This outfit is grounded and sure of itself, making it perfect for walks in the country or dressy casual events. It’s a lesson in how to layer clothes so that they look so elegant.