17 Classy Old Money Skirt Outfits for Women

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Old money style is all about quiet confidence. It’s polished without being flashy, elegant without trying too hard. When it comes to skirts, this aesthetic focuses on clean lines, timeless fabrics, and outfits that feel refined and intentional.

Think structured blazers, crisp blouses, neutral tones, and silhouettes that never go out of style. These are outfits you’d wear to a nice lunch, a museum visit, or an afternoon coffee at a classic café.

If you love a classy, put-together look that feels effortless and elevated, these 17 old money skirt outfits will give you plenty of inspiration.

1. Pleated Mini Skirt with Trenchcoat and High Boots

This outfit feels effortless while still looking very intentional.

2. Satin Skirt with Crop Shirt

This look works beautifully for lunch dates or elegant daytime outings.

3. Pleated Midi Skirt with Crisp White Button-Up

A pleated midi skirt paired with a tucked-in white button-up is the definition of timeless elegance. Add loafers or low heels and minimal jewelry for a clean, refined finish.

4. Tweed Skirt with Fitted Knit Top

Tweed instantly gives old money energy. Pair a tweed skirt with a fitted knit top in a neutral shade like cream or beige. Finish with classic flats or pumps.

5. Black Mini Skirt with Trenchcoat

This is an outfit you can wear to a nice lunch, or an afternoon coffee at a classic café.

6. A-Line Skirt with Structured Blazer

An A-line skirt combined with a tailored blazer creates a polished silhouette that feels confident and sophisticated. Stick to neutral tones like navy, camel, or grey.

7. Satin Midi Skirt with Cashmere Sweater

A satin midi skirt paired with a soft cashmere sweater feels luxurious but understated.

8. Pencil Skirt with Silk Blouse

A well-fitted pencil skirt and silk blouse is a classic old-money combination. Choose muted colors and keep accessories simple for a refined look.

9. Satin Maxi Skirt With Oversized Coat

This outfit looks especially trendy and stunning, and you can rock it with flat shoes or low heels.

10. Goth-inspired Skirt Outfit

If you love a stunning, well put-together look that feels effortless, then this is for you.

11. Wool Midi Skirt with Turtleneck

For cooler days, a wool midi skirt and fitted turtleneck is both practical and elegant. Add ankle boots or loafers to complete the outfit.

12. Plaid Skirt with Cream Cardigan

A plaid skirt styled with a soft cream cardigan gives a subtle preppy feel.This outfit looks especially chic with ballet flats or low heels.

13. High-Waisted Skirt with Belted Blazer

A high-waisted skirt paired with a belted blazer highlights the waist while keeping the look tailored and sophisticated. Neutral shades keep it timeless.