Old money style always makes me think of effortless elegance mixed with just the right amount of confidence. I love how the look feels polished without ever seeming like it’s trying too hard. Summer is the perfect season for it too because lightweight fabrics and classic cuts make these outfits even more appealing.
I’ve found myself drawn to crisp linen shirts, tailored shorts, and those timeless loafers that instantly give an outfit character. There’s something so charming about a man who can look sharp and relaxed at the same time. These are the kinds of outfits that never go out of style and I can’t wait to share my favorite summer picks.
Polo and Tailored Shorts Perfection
This look captures a classic summer staple with a white polo neatly tucked into navy tailored shorts. A brown leather belt ties it all together, while loafers finish the outfit with ease. The fit is clean, the lines are sharp, and the whole vibe gives off quiet confidence in front of that grand white-columned home.
I love how simple pieces can create such a strong statement. This outfit shows that looking refined doesn’t require layers or fuss, just timeless staples styled right. It feels effortless yet undeniably polished, the kind of look that instantly makes me think of country clubs and weekend getaways.
Navy Polo and White Trousers Cool
Here we have a dark navy polo paired with crisp white trousers that look perfect for a sunny day out. The outfit is elevated by suede loafers and a straw hat, bringing both function and style to the scene. With the palm trees and vintage car, the entire look feels like an editorial moment made for summer.
I can’t get enough of this balance between casual and elegant. The navy and white combo is so refreshing, and the accessories add personality without being loud. To me, this is the kind of style that whispers wealth instead of shouting it.
Light Blue Suit with Relaxed Ease
This man wears a pale blue linen suit layered over a white crewneck tee, giving tailored suiting a fresh summer update. The addition of brown tassel loafers makes the look feel elevated but approachable. He’s holding sunglasses, standing on a terrace overlooking the sea, which makes the whole outfit shine even more.
I adore how this suit manages to look formal and relaxed all at once. The choice of a tee instead of a shirt makes it modern, yet it still feels timeless. It’s exactly the kind of outfit that proves old money style doesn’t have to be stiff.
Beige Polo and Matching Chinos
Here’s a tonal look done beautifully with a cream knit polo tucked into tan chinos. A matching jacket is casually draped over the shoulder, while rich brown loafers complete the outfit. Walking down a cobblestone street, this look feels sophisticated but easy.
I think there’s something undeniably chic about matching tones head to toe. It feels quiet, intentional, and very refined. This is the type of style I imagine on someone who appreciates the little luxuries in life, like slow travel and long lunches outdoors.
Striped Shirt and Linen Blazer Classic
This outfit brings together a light striped button-down shirt with a beige linen blazer and crisp white trousers. Suede loafers in a soft shade pull the look together, while the man enjoys an espresso outside a café with a book in hand. It’s stylish, timeless, and wonderfully European.
I love how this look tells a story without saying a word. It’s relaxed but not sloppy, stylish but not overdone. Honestly, it feels like the dream summer uniform for anyone who appreciates both comfort and sophistication.
Navy Shirt and White Shorts Charm
This relaxed outfit features a dark navy linen shirt with rolled sleeves paired with clean white shorts. Accessories stay simple with a straw hat carried casually in one hand. Standing barefoot on a dock by the water, the look feels breezy yet incredibly chic.
I think this is such a beautiful mix of rugged and refined. The open shirt gives a carefree feel, but the tailored shorts keep it polished. It’s the kind of summer look that makes me want to book a holiday by the coast immediately.
Double Breasted Linen Suit Power
Here we see a beige double-breasted linen blazer paired with cream trousers and tan loafers. A patterned silk scarf and pocket square add a touch of personality and refinement. The overall look is sharp, classic, and incredibly sophisticated, perfect for a seaside city stroll.
To me, this outfit is pure confidence. It’s bold but not flashy, stylish yet practical for warm weather. I think it’s the kind of style that makes an impression without even trying, which is exactly what old money dressing is all about.
Soft Yellow Polo with Summer Brightness
This outfit pairs a pale yellow polo with cream trousers, finished with brown loafers and a matching belt. The short sleeves and light palette feel airy, while a glass of wine in hand adds to the relaxed luxury vibe. It’s a look that feels just right for a sunny afternoon spent socializing.
I really like how cheerful this feels without being loud. The yellow brings warmth and personality, while the tailored fit keeps it elegant. It’s one of those outfits that makes me think of garden parties and long afternoons on the terrace.
Vineyard Style with Natural Ease
Here we see a linen shirt in a soft beige tone, paired with olive green trousers and brown loafers. The shirt is worn casually with the sleeves rolled, and the woven belt ties in perfectly with the vineyard backdrop. Holding a glass of red wine, the whole look feels charming and approachable.
This one makes me smile because it shows how old money style can be down to earth. It feels polished yet easy, with a relaxed confidence that’s so attractive. Honestly, it makes me think of someone who appreciates the finer things but never takes himself too seriously.
Crisp White Suit by the Marina
This outfit showcases a white linen suit worn with a sky blue shirt, styled open at the collar for a breezy effect. Brown tassel loafers and a matching belt complete the look, while aviator sunglasses and a pocket square add polish. Standing against the backdrop of a sailboat, the vibe is coastal luxury at its best.
I find this look irresistible because it feels both commanding and carefree. The mix of white and light blue is fresh, and the details make it stylish without being flashy. It’s exactly what I picture when I think of summer sophistication by the sea.
Safari Jacket and Shorts Relaxation
Here’s a look with more rugged charm, featuring a tan safari jacket over a white shirt paired with brown tailored shorts. Dark leather sandals and a large leather weekender bag complete the ensemble. Seated on a garden bench, the outfit feels grounded but undeniably chic.
I love how practical this outfit feels while still keeping its elegance. The safari jacket adds character, while the shorts and sandals keep it relaxed for warm days. It’s the kind of style that feels equally at home in the countryside or at a resort.
White Linen Shirt with Beach Confidence
This man wears a crisp white linen shirt tucked into cream shorts, styled with a braided leather belt and light slip-ons. The shirt is open at the neck, and aviator sunglasses give it a timeless edge. Walking across a sandy beach, the whole outfit feels relaxed yet elevated.
To me, this outfit is summer perfection. It’s easy, breathable, and polished enough to look sharp while staying comfortable. I think it captures that old money beach aesthetic that’s both carefree and quietly refined.
Light Grey Blazer with Ivy Backdrop
This outfit features a light grey linen blazer over a white shirt, paired with beige chinos and black loafers. The backdrop of an ivy-covered estate makes the entire look even more charming. With his silver hair styled effortlessly, the overall vibe is classic and distinguished.
I adore this look because it shows how subtle colors can still make a big impression. It feels elegant without needing bold choices, and the ivy setting makes it almost cinematic. It’s definitely the kind of outfit that feels timeless year after year.
Navy Tee and White Linen Ease
Here’s a more relaxed take with a navy crewneck tee layered under an open white linen shirt, paired with crisp white trousers. Navy loafers keep the look cohesive, while a straw hat rests on the seat beside him. Sitting on a boat, it’s the epitome of summer leisure with polish.
I really like how approachable this feels while still keeping its sophistication. The combination of navy and white is clean, and the open shirt gives it an easy energy. It’s the kind of outfit I picture on summer boat days when style and comfort meet perfectly.
White Linen Shirt with Harbor Style
This outfit keeps things sharp and simple with a crisp white linen shirt paired with beige tailored shorts. Brown loafers and a matching leather tote bag add polish, while aviator sunglasses tie the look together. The marina backdrop with yachts makes it feel effortlessly luxurious.
I think this outfit nails that summer-smart balance. It’s practical for the heat yet still refined, the kind of style that says vacation but never sloppy. Honestly, it’s one of those looks that makes me want to spend an afternoon strolling along the harbor.
Neutral Linen Suit with City Confidence
Here we have a beige linen suit worn with a classic white shirt, finished with brown loafers. The jacket is tailored but relaxed, and a subtle pocket square adds personality. Walking through the city, the look feels crisp and timeless, perfect for warm weather sophistication.
I love this one because it proves that linen suits don’t have to look rumpled or casual. When styled well, they can be incredibly chic and powerful. To me, this is the ultimate city look for summer, blending comfort with pure old money elegance.
