The allure of ‘Old Money’ style transcends fleeting trends, embodying a timeless elegance rooted in quality, understated luxury, and impeccable taste. At the heart of this enduring aesthetic lies the long skirt- a versatile garment that exudes sophistication and grace. Far from being old-fashioned, the long skirt, when styled correctly, becomes a canvas for creating looks that whisper refinement rather than shout opulence. If you’re ready to infuse your wardrobe with a sense of enduring class, join us as we explore 18 exquisite long skirt outfits that perfectly capture the essence of ‘Old Money’ chic.
The Core Principles of Old Money Style
Before diving into specific outfits, understanding the foundational elements of ‘Old Money’ fashion is key. It’s not about flashy logos or trendy pieces, but rather an appreciation for craftsmanship, enduring design, and a quiet confidence. Think quality fabrics, tailored fits, and a palette of sophisticated neutrals and muted tones. The goal is to look effortlessly polished, as if your style is innate rather than contrived.
Essential Long Skirt Silhouettes and Fabrics
The long skirt itself offers a myriad of styles, each contributing uniquely to the ‘Old Money’ aesthetic. Look for:
- A-Line Skirts– Universally flattering, offering graceful movement.
- Column or Pencil Skirts– Sleek and sophisticated, perfect for tailored looks.
- Pleated Skirts– Adding texture and a touch of classic charm.
- Wrap Skirts– Effortlessly chic and adjustable.
- Fabrics– Prioritize natural fibers like wool, cashmere, silk, linen, tweed, and high-quality cotton blends. These drape beautifully and possess a luxurious feel.
18 Exquisite Old Money Long Skirt Outfits
Here are 18 ways to style long skirts with an unmistakable ‘Old Money’ flair, focusing on elegance, quality, and timeless appeal.
1. The Tailored Tweed Skirt Ensemble
Pair a structured tweed long skirt in muted grey or beige with a fine-gauge merino wool turtleneck. Add classic leather loafers and a simple leather shoulder bag for a sophisticated daytime look.
2. Silk Slip Skirt and Cashmere Sweater
A flowing silk slip skirt in champagne or ivory, worn with an oversized yet refined cashmere sweater in a complementary neutral. Finish with delicate ballet flats and a pearl pendant necklace.
3. Pleated Midi Skirt with a Crisp Blouse
A finely pleated midi skirt in a deep jewel tone or classic navy, teamed with a crisp white button-down shirt. Tuck it in for a polished silhouette. Kitten heels and a structured top-handle bag complete this elegant outfit.
4. A-Line Wool Skirt and Fitted Turtleneck
Choose a rich camel or charcoal A-line wool skirt. Pair it with a perfectly fitted black or cream turtleneck. Accessorize with ankle boots and a tailored wool coat for colder weather.
5. Linen Maxi Skirt for Summer Elegance
A breathable linen maxi skirt in white or sand, paired with a simple silk camisole and a lightweight cashmere cardigan draped over the shoulders. Espadrille wedges and a woven tote are ideal.
6. Satin Skirt with a Structured Blazer
Elevate a black or deep green satin long skirt with a perfectly tailored, slightly oversized blazer in tweed or wool. A delicate silk tank underneath and pointed-toe pumps create a chic evening ensemble.
7. Column Skirt and Fine Knit Top
A sleek column skirt in a dark neutral like charcoal or forest green, paired with a finely knitted, short-sleeved top. Keep accessories minimal- a delicate gold bracelet and small stud earrings.
8. Checked Skirt and Classic Button-Down
Embrace a subtle plaid or houndstooth long skirt. Wear it with a classic light blue button-down shirt, tucked in. Add leather ankle boots and a belt with a discreet buckle.
9. Navy Pencil Skirt Power Look
A refined navy pencil skirt that hits below the knee, paired with a silk cream blouse and a tailored navy blazer. Classic pumps and a structured briefcase-style handbag convey confidence.
10. Flowing Chiffon Skirt for Evening
A delicate, flowing chiffon maxi skirt in a deep, rich color like burgundy or emerald. Pair it with a fitted silk top and elegant strappy heels for a sophisticated evening event.
11. Wrap Skirt and Simple Tee
A high-quality cotton or linen wrap skirt in an earthy tone, combined with a perfectly fitted, plain white or black crew-neck tee. Simple leather sandals and a woven clutch keep it understated.
12. Broderie Anglaise Skirt for Resort
For a sophisticated resort look, choose a white broderie anglaise maxi skirt. Pair it with a simple, fitted knit top in a pastel shade and espadrille flats. Add oversized sunglasses.
13. Corduroy Maxi Skirt for Autumn
A rich, earthy-toned corduroy maxi skirt (think forest green or rust) styled with a cream cable-knit sweater. Brown leather boots and a simple cross-body bag are perfect for fall outings.
14. Leather-Trimmed Skirt Sophistication
A long wool skirt featuring subtle leather trim or detailing. Pair with a black long-sleeve silk top and elegant black pumps. A minimalist watch and small diamond earrings complete the look.
15. Asymmetrical Hem Skirt with a Cardigan
An elegant long skirt with a subtle asymmetrical hemline in a solid color. Team it with a fine cashmere cardigan, buttoned up, and delicate slingback heels. A small, elegant clutch is ideal.
16. Patterned Skirt with a Solid Top
Opt for a long skirt with a tasteful, subtle pattern- perhaps a delicate floral or a muted geometric. Pair it with a solid-colored silk or fine knit top that picks up one of the skirt’s accent colors.
17. Velvet Skirt for Winter Glamour
A luxurious velvet maxi skirt in a deep jewel tone like sapphire or ruby. Pair with a fitted black cashmere sweater or a silk camisole under a tailored blazer. Elegant heeled boots add warmth and style.
18. Minimalist Black Maxi Skirt
The ultimate versatile piece- a well-cut black maxi skirt in wool or a high-quality blend. Style it with a simple white tee, a classic trench coat, and elegant white sneakers for a sophisticated casual look, or dress it up with a silk blouse and heels.
Perfecting Old Money Accessories
Accessories are the silent narrators of ‘Old Money’ style. They are chosen for their quality, timelessness, and ability to enhance, not overpower, an outfit.
- Jewelry– Pearls (earrings, necklaces), delicate gold or silver pieces, minimalist watches. Avoid anything overtly flashy.
- Handbags– Structured leather bags (Hermès Kelly, Chanel Classic Flap inspired), classic shoulder bags, woven totes for summer. Quality over quantity.
- Shoes– Loafers, ballet flats, low block heels, kitten heels, classic pumps, elegant ankle boots, espadrilles. Comfort and understated elegance are key.
- Scarves– Silk scarves tied elegantly around the neck, in the hair, or on a handbag handle add a touch of refinement.
- Eyewear– Classic shapes like cat-eye or oversized round sunglasses.
Old Money Long Skirt Styling- Dos and Don’ts
Dos
- Do invest in high-quality fabrics that drape well and last.
- Do stick to a neutral and muted color palette, occasionally adding a rich jewel tone.
- Do ensure your clothes are perfectly fitted and well-maintained.
- Do layer with intention- a cashmere cardigan or a tailored blazer.
- Do choose classic, timeless accessories.
Don’ts
- Don’t over-accessorize or wear too many statement pieces.
- Don’t opt for overly trendy or fast-fashion items.
- Don’t wear ill-fitting or poorly constructed garments.
- Don’t display prominent logos or brand names.
- Don’t neglect grooming- polished hair and subtle makeup are essential.
