21+ Perfect Old Money Summer Outfits You’ll Want to Wear All Season Long

If you’ve been eyeing those effortlessly chic summer looks all over Pinterest and TikTok, you’re probably already into the old money aesthetic. It’s that clean, timeless style—lots of linen, tailored shorts, striped knits, and neutral tones—that somehow makes you look put together without even trying.

Old money summer outfits are all about looking casual but elevated. You don’t need loud logos or trendy pieces—just classic staples that feel expensive (even if they’re not). So if you’re ready to build your dream summer wardrobe, I’ve rounded up the best old money summer outfit ideas to get you inspired.

Striped Sweater & Black Dress

Simple but elevated, this look leans into quiet luxury with a classic black dress as the base. The fit is easy and flattering, paired effortlessly with a chunky striped sweater draped over the shoulders for that preppy, old money feel. Black slide sandals and an ivory leather bag keep it relaxed but still refined.

Vest & Tailored Shorts

This look is the definition of polished summer style. The cream buttoned vest adds structure and a bit of a vintage touch, while the black tailored shorts keep things modern and city-ready. Two-tone slingback heels give off that classic Parisian flair, and the quilted Chanel bag pulls everything into that old money aesthetic.

Striped Tank & Linen Trousers

Nautical, but make it old money. The striped halter-style tank adds a playful, coastal vibe while the crisp white linen trousers keep things classic and breathable. A brown leather belt and matching Hermès-inspired sandals tie the look together with quiet luxury energy.

The structured straw tote leans into that “summering in the South of France” mood, and round sunnies give it a touch of vintage charm. It’s relaxed, polished, and timelessly chic.

Linen Shirt & White Shorts

Light, fresh, and effortlessly elevated. A soft blue linen button-down paired with tailored white shorts feels crisp without being fussy. The tan belt and matching Hermès-inspired sandals create a warm contrast, while the structured leather handbag brings that classic old money polish.

Sun Hat & Crochet Skirt

This look feels straight out of a Riviera postcard. The structured black-and-white swimsuit doubles as a top, giving just the right amount of contrast against the breezy white crochet skirt. A wide-brimmed straw hat with a black ribbon adds instant elegance, and the woven espadrilles keep things laid-back but refined.

Asymmetrical Top & Black Shorts

Chic with a twist, this outfit blends classic and contemporary in the best way. The asymmetrical cream top with a built-in scarf detail adds a touch of drama, while the black tailored shorts keep things grounded and minimal. Two-tone ballet flats lean into that timeless Parisian feel, and a small structured bag ties everything together.

Sun Hat & White Shorts

This look is effortlessly sleek with a nautical edge. A fitted black tank tucked into high-waisted white shorts keeps the silhouette clean and classic, while the slim black belt and heeled sandals dress it up just enough.

White Halter Dress

Clean, crisp, and effortlessly refined. This white halter dress gives classic summer energy with its tailored bodice, cinched waist, and flowy midi skirt. The collared neckline adds a hint of structure, while the lightweight fabric moves beautifully in the breeze.

Paired with neutral heels, dark sunnies, and a textured clutch, it’s an easy way to look pulled together without overthinking it—very old money on holiday.

Vest & Trousers

Nothing says timeless quite like a camel and cream combo. The structured vest brings in that tailored, old money vibe, while the relaxed wide-leg trousers soften the look in the best way. Two-tone ballet flats and a quilted Chanel bag add layers of polish without going over the top.

Linen Set & Sun Hat

All-white done right feels effortlessly rich. The textured buttoned top and wide-leg trousers create a look that’s tailored but relaxed, like something you’d wear while sipping espresso by the lake. A structured white bag adds polish, while the wide-brim straw hat keeps it cool and timeless.

Simple black sandals ground the outfit without stealing attention—quiet luxury through and through.

Black Dress & Straw Hat

Sun, sea, and an effortlessly elegant black dress—this look checks all the right boxes. The strappy silhouette is simple yet striking, flowing into a full skirt that catches the breeze just right. A wide-brim straw hat with a black ribbon adds that old-money touch, and a structured woven bag finishes things off with quiet ease.

White Vest & Satin Skirt

Monochrome moments always hit different. The structured white vest adds a tailored edge, balanced beautifully by the soft, satin-like midi skirt. White Hermès-inspired slides and a chic mini Marni tote keep things playful but elevated.

Striped Skirt & Crop Top

Breezy and bold, this outfit is giving luxe beachside energy. The black cropped tank keeps it sleek up top, while the striped crochet maxi skirt adds texture and a fun coastal feel. A straw hat with a black ribbon brings that timeless elegance, and the Celine basket bag seals the deal.

Linen Dress & Black Accessories

So classic, so easy. The sleeveless white linen dress with its row of dark buttons gives a clean silhouette that flatters without trying too hard. Paired with black accents—a structured mini bag, strappy sandals, and a wide-brim hat—it’s giving quiet elegance in the middle of a sunny city day.

Halter Top & White Skirt

Black and white never fails. The halter-style top adds a subtle touch of drama, balanced by the voluminous white midi skirt that feels both crisp and airy. A wide belt cinches the waist for structure, while black slide sandals and a woven clutch keep things grounded and unfussy.

Polka Dot Dress & Tan Bag

Old-school glamour meets modern resort elegance. The structured polka dot midi dress brings in all the retro charm with its flattering square neckline and full skirt. Strappy sandals and oversized sunnies keep things relaxed, while the tan Hermès bag adds a refined, grounded touch.

Cream Set & Black Accents

Matching sets just have a way of looking instantly put-together. This cream two-piece—featuring a structured short-sleeve top and pleated midi skirt—feels classic with just the right amount of polish. The black trim ties everything together with a crisp contrast, especially when paired with black heels and a timeless quilted Chanel bag.

White Button-Down & Black Shorts

Buttoned-up but never boring. Rolled sleeves, tucked-in tailoring, and a cinched waist give this outfit its structure, while warm brown leather accents add that touch of grounded elegance. The look leans minimal, but the details—gold jewelry, sleek sunglasses, and a straw bucket bag—bring just enough personality.

Black Top & Pleated Skirt

Minimalist, but far from plain. The sleek black top adds just enough structure to balance the soft movement of the ivory pleated skirt. Instead of over-accessorizing, the look stays sharp with black flip-strap heels and a small woven top-handle bag.

Strapless Top & Maxi Skirt

Head-to-toe black never looked so breezy. A strapless top balances the volume of a full maxi skirt, cinched in with a bold belt for just the right amount of structure. White and black cap-toe ballet flats break things up while keeping it classic, and the curved mini bag adds a sleek, modern touch.

Striped Shirt & Cream Shorts

Sharp lines meet soft neutrals in this effortlessly tailored combo. The black-and-white striped button-down adds just the right amount of structure, while the cream pleated shorts keep things light and refined. Tan leather accents from the belt and shoulder bag warm up the palette, and black slides bring the whole look back to earth.

Cream Vest & Pleated Skirt

Soft pleats and structured tailoring make a dreamy pairing here. The cropped cream vest feels polished without being too buttoned-up, while the flowing skirt adds just the right amount of movement. Minimal white sandals and a textured top-handle bag keep the look effortless.

Loved these looks? You can check out my old money summer outfits from last year for even more timeless inspo—and if you’re building your wardrobe, don’t miss my old money summer wardrobe edit too. So many classic pieces you’ll want on repeat.