Old Money’s guide to the best men’s summer 21 outfits ideas

Have you ever glanced at a gentleman and immediately sensed a heritage of sophistication? As we edge into Summer 2024, the ‘Old Money’ aesthetic offers more than just clothes—it presents a narrative. What distinguishes a casual summer ensemble from one steeped in old money tradition? How can one convey an air of legacy and luxury, even in the most modest wear? This exploration of sartorial elegance will unravel the enigma wrapped in linen and loafers.

Classic Beachfront Elegance

The serene backdrop of a beach at dusk sets the stage for a look that’s both relaxed and refined. A man stands poised on a wooden pathway, his attire a study in understated elegance, perfect for a summer wedding by the sea.

• Shirt: The olive green button-up, casually unbuttoned at the top, whispers effortless chic.
• Trousers: His white slacks, crisply ironed, suggest a man who is at ease with luxury.
• Shoes: Dark brown loafers, sockless, champion a blend of comfort and class.

The silhouette is ideal for a mid-size figure, offering breathability and a timeless look. This outfit could carry one from a beachside stroll to a casual office gathering without missing a beat. However, it might not translate as well to an urban night out or more formal events.

If I were to augment this style, a watch with a leather strap would be my go-to accessory—complementing the earth tones while respecting the outfit’s modesty. A belt, while often a staple, would be superfluous here, preserving the clean lines of the trousers.

Understated Courtyard Chic

A man stands confidently outside an elegant building, embodying the old money vibe with a modern twist, perfect for a leisurely day in the heart of Italy.

• Shirt: The light blue button-down, sleeves rolled up, strikes a balance between work and play.
• Trousers: Olive trousers offer a grounding contrast to the light shirt, fitting for a man with a curvy or athletic build.
• Sandals: Brown leather sandals add a touch of easy-going refinement.

This ensemble would shine at a casual brunch or an office where the dress code leans towards the relaxed. Yet, for more active occasions or cooler climates, it may not be the most practical choice.

To elevate this attire, I’d suggest a belt to seamlessly tie the shirt and trousers together. On the flip side, avoid overly embellished sandals or flashy watches, which could distract from the outfit’s subtle sophistication.

Seaside Sophistication

Against the iconic scenery of a coastal town, a man’s outfit exudes a sense of old-world luxury, ideal for a summer vacation or a casual outing.

• Shirt: The short-sleeved geometric print shirt is playful yet posh.
• Trousers: White trousers complement the shirt, adding a bright, summery touch.
• Sandals: Simple brown sandals affirm a laid-back yet polished air.

This get-up is perfect for those balmy summer days when the agenda calls for comfort without compromising on style. It’s less suited for formal events or traditional office settings.

To complete this look, a pair of sunglasses with a vintage frame would not only be practical but also reinforce the old money aesthetic. A no-go would be anything too modern or sporty, like a digital watch or athletic sneakers, which would clash with the classic vibe.

Lakeside Leisure

By a tranquil lake, a young man’s attire encapsulates the essence of old money, refreshed for today’s aesthetic man.

• Shirt: His striped short-sleeve button-up with a relaxed collar is the epitome of summer smart.
• Shorts: The white shorts are both chic and casual, suitable for a variety of summer activities.
• Shoes: Clean white sneakers offer a nod to modernity while keeping the look crisp.

This ensemble is a masterclass in versatility, equally at home on a boat or at a backyard soiree, yet might be too casual for a wedding or more solemn occasions.

Urban Summer Refined

In an urban setting, this style demonstrates how to dress for summer in the city with a nod to old money roots.

• Shirt: The beige polo is casual yet sophisticated, embodying the old money’s penchant for understated tones.
• Trousers: Paired with flowy grey trousers, the ensemble is appropriate for a day out or an informal office setting.
• Accessories: The sunglasses and subtle wristwatch add a layer of discreet luxury.

This look speaks to the man who values comfort as much as style, perhaps not as suitable for men who favor a more fitted silhouette or for very formal business environments.

Urban Textures

Here we have an amalgamation of texture and tone that brings a new depth to the term ‘street style’. The man in the image exudes confidence, his outfit a perfect blend for the aesthetic man, who is both a part of the bustling city life yet stands out with an air of old money sophistication.

• Top: The textured brown t-shirt with subtle stripes complements his lean physique and is an excellent option for men who prefer a fitted yet not overly tight top.
• Trousers: The high-waisted linen trousers bring a vintage feel that’s both stylish and breathable for the summer heat.
• Footwear: Classic white sneakers ensure comfort and add a clean, modern edge to the look.

This ensemble is not suited for formal occasions or traditional office settings but perfect for an art gallery visit or a casual coffee date. To further this style, a sleek leather belt could accentuate the waistline, whereas bulky or overly casual accessories like rubber wristbands would detract from its elegance.

Retro Refreshed

A sartorial nod to the past with a zest of contemporary charm, this look makes for a perfect boy outfit for those warm, lazy afternoons or a casual, chic vacation look.

• Shirt: The burnt orange shirt, with its relaxed fit and open collar, adds a vintage-inspired vibe that’s bang on trend.
• Trousers: Paired with classic white jeans, the look is kept light and summer-ready.
• Accessories: Minimal jewelry and clear-framed glasses add a touch of personality without overpowering the outfit.

While ideal for a casual outing or a summer festival, this outfit might not align with formal wedding attire requirements. To enhance this outfit, one could add a Panama hat for a touch of dapper flair, but a full black ensemble would overshadow this look’s breezy nature.

Coastal Classic

As if he’s just stepped off a sailboat in Sicily, this man’s attire is a testament to the timeless appeal of the old money aesthetic, ideal for a wedding by the shore or a summer soirée.

• Shirt: The white linen shirt, unbuttoned for a relaxed feel, oozes effortless style.
• Shorts: The patterned blue shorts add a touch of playfulness and are a great fit for men with a mid size build.
• Shoes: The brown suede loafers are the epitome of old money casual – stylish yet understated.

This ensemble would be out of place in a strict office environment but is the epitome of vacation chic. An addition of a lightweight blazer could transition this look to a smart-casual evening event, but sporty sandals would break its harmonious blend.

Polished Poise

Here’s an outfit that marries the old money aesthetic with a sharp, modern edge, perfect for the man who strides through the urban landscape with a nonchalant grace.

• Shirt: The cream ribbed short-sleeve polo shirt fits snugly, accentuating a well-toned torso without being overly tight.
• Trousers: The tailored brown trousers are a classic choice that can bridge the gap between office and casual wear.
• Accessories: The dark sunglasses add an air of mystery and a full black touch to the ensemble.

While this outfit could impress at a casual office, it’s less suitable for high-humidity conditions given its more fitted nature. A leather-strap watch could complement this outfit well, whereas a bright pink or loud-patterned tie would disrupt its refined color palette.

Yacht Week Ready

Capturing the essence of a summer adventure, this outfit screams old money vacation wear, perfect for a young man about to set sail on the Mediterranean.

• Shirt: The airy, lime-green linen shirt is both cool and casual, perfect for a day on the water.
• Shorts: The light-colored shorts provide a comfortable yet stylish base, ideal for men of all sizes.
• Accessories: The absence of shoes underscores the leisurely vibe, and the necklace adds a personal touch.

This style is perfect for a vacation or a weekend getaway, but it might not transition well to an urban environment or a formal occasion. To top off this look, a pair of stylish sunglasses would not only be practical but also add a layer of chic sophistication. However, formal leather shoes would be at odds with this relaxed aesthetic.

Sartorial Sophistication

This image presents a gentleman standing by a grand doorway, embodying the quintessential old money style with a contemporary twist—impeccable for a summer wedding or a high-profile office.

• Shirt: The white linen shirt, open at the collar, exudes a breezy formality.
• Trousers: Cream trousers offer a refined counterpoint, maintaining the outfit’s airy feel.
• Shoes: Tassel loafers in a rich brown tone anchor the look with a classic, luxurious touch.

This outfit would work well for a variety of body types, offering a generous fit without sacrificing a tailored appearance. A setting like an outdoor wedding or an upscale brunch spot would be ideal, whereas it might feel out of place at a casual beach gathering. Adding a silk pocket square could introduce a splash of color, but a tie might formalize the ensemble too much.

Contemporary Comfort

A perfect blend of casual comfort and classic charm, the ensemble in this image suits the relaxed yet refined man enjoying a panoramic view of a cityscape.

• Top: The textured, off-white vest layered over a simple tee suggests a laid-back approach to classic style.
• Bottoms: Coordinating trousers, loose-fitting and comfortable, complement the relaxed upper half.
• Shoes: Black and white loafers add an unexpected, modern twist to the traditional palette.

Ideal for the creative professional or the weekend explorer, this outfit wouldn’t be the first choice for a formal occasion or a business meeting. To personalize this look, a vintage wristwatch would be an excellent addition, while flashy jewelry would be less harmonious.

Casual Urbanity

In a scene that merges old money finesse with urban practicality, we see a style that works for the man who moves seamlessly from the office to after-work engagements.

• Shirt: The sky-blue button-down paired with a dark jacket slung over the shoulder strikes a balance between business and leisure.
• Pants: The dark, pleated trousers add a touch of gravity and office appropriateness.
• Footwear: Classic leather shoes complete the ensemble, embracing a more formal edge.

This outfit could cater to most male figures and environments, from office buildings to evening events. A leather belt would be a suitable addition for a touch of formality, but avoid anything too casual like sneakers or sportswear, which would detract from the outfit’s polished aesthetic.

Timeless Elegance

This image captures the essence of a leisurely summer day with an outfit that marries comfort with the undying charm of old money style.

• Shirt: The crisp white button-down is both versatile and timeless, a must-have in any wardrobe.
• Trousers: Paired with dark trousers, the ensemble remains grounded and masculine.
• Shoes: Suede loafers in a dark shade round off the look with a nod to both comfort and class.

Suitable for various occasions, from casual office days to weekend outings, this attire would flatter a variety of body types. Adding a statement watch could provide a focal point, yet bright colors or busy patterns should be avoided to maintain the outfit’s integrity.

Resort Ready

The following outfit exudes relaxed luxury, perfect for a vacation at a resort or a day at the yacht club.

• Shirt: A light blue linen shirt, slightly undone, keeps the vibe carefree yet chic.
• Shorts: Paired with white shorts, the outfit remains summery and sophisticated.
• Accessories: The leather travel bag and loafers suggest a readiness for adventure without sacrificing style.

This ensemble is versatile enough to suit different body shapes and sizes, and it’s particularly fitting for a summer vacation or a casual day out. A classic watch would be a welcome addition, but sporty attire would shift the look away from its old money roots.

Nautical Nuances

In a harmonious blend of navy and stripes, this outfit stands against a dusk-toned sky, exuding a sense of contemplative elegance that would be right at home on a summer evening by the marina.

• Shirt: The navy blue, striped, short-sleeved shirt offers a maritime nod, ideal for a mid-size build looking for a balance between fit and comfort.
• Trousers: The dark trousers provide a sleek contrast, their tailored cut suggesting a sophisticated approach to summer evenings.
• Pose: The relaxed stance of the subject further accentuates the wearability of the outfit, suitable for a variety of casual and semi-formal occasions.

This look would shine at an outdoor dinner or a coastal resort setting. Enhancing this with a pair of elegant sunglasses would be fitting, while a baseball cap or sneakers might detract from its refined appeal.

Retro-Inspired Relaxation

Against a warm, yellow wall, this image captures the easy-going spirit of summer with a hint of retro charm, perfect for an afternoon stroll through the city or a casual meet-up.

• Shirt: The striped polo, with its warm hues, brings a touch of ’70s inspo to a modern-day outfit.
• Trousers: The light khaki pants complement the shirt’s casual vibe, making them versatile for both a modest outing or a casual day at the office.
• Accessories: A leather bag and loafers add a functional yet stylish element to the ensemble.

While the look is relaxed, it maintains an element of intention, making it unsuitable for more formal settings but perfect for a day out. A watch could be a great addition, whereas bright, flashy sandals would clash with the outfit’s subdued tones.

Beachside Serenity

Here’s a style that echoes the tranquility of a seaside promenade, ideal for a day of relaxation or a modest retreat away from the hustle of city life.

• Top: The oversized beige shirt, half-buttoned, speaks to the laid-back nature of the outfit.
• Bottoms: White trousers match the shirt in their relaxed fit and vacation vibe.
• Footwear: Minimalist sandals are the footwear of choice for comfort and ease, suitable for a variety of sizes and shapes.

Perfect for a day at the beach or a casual brunch, this outfit might be too relaxed for more traditional settings. To add a bit of personality, a tasteful hat would work well, while sneakers might make the ensemble too sporty.

Timeless Tones

Embracing the balmy climes, this ensemble blends neutral tones with classic style, picturing a man ready for a chic yet comfortable summer outing.

• Shirt: The light polo shirt is understated yet sophisticated, suitable for various occasions and sizes.
• Shorts: The olive shorts break the monochrome and add a subtle dash of color.
• Accessories: The watch and espadrilles round off the look with a practical touch.

This look would be a great choice for a summer lunch or an outdoor gathering, not as much for formal events. A simple addition like a leather belt would enhance the outfit, while bright, patterned shirts would disrupt the serene color scheme.

Resort Chic

In a symphony of pastels, this look encapsulates the essence of a summer resort vibe, perfect for a man who balances leisure with elegance.

• Shirt: The light green button-down, paired with soft pink shorts, creates a look that’s fresh and refined.
• Stance: The confident pose signals a comfort with personal style and a readiness for summer activities.
• Watch: The presence of a classic timepiece suggests an appreciation for finer details.

Ideal for a vacation or a relaxed day out, it wouldn’t fit the dress code of a corporate environment. A subtle addition could be a pair of loafers, which would maintain the outfit’s chic feel, while overly casual flip-flops or a backpack would downplay its sophistication.

Each outfit detailed here reflects the versatility and timeless appeal of the old money style—rooted in tradition but always open to a breath of fresh air.

Desert Explorer

Amidst the grandeur of ancient architecture, this outfit merges the spirit of adventure with the understated elegance of summer refinement.

• Shirt: A white patterned short-sleeve button-up shirt captures the eye, striking the perfect balance between detail and simplicity.
• Shorts: The tailored khaki shorts are both practical and stylish, cut to a length that’s smart yet suitable for warm climates.
• Footwear: Dark brown leather sandals add a rugged yet sophisticated finish to the look.

This outfit is a canvas of versatility, apt for a variety of body types and ideal for vacation exploration or a weekend retreat. While it exudes a laid-back confidence, it would be out of place in a formal setting. A wristwatch with a leather strap could be a subtle yet fitting accessory, whereas sporty sneakers or loud prints would disrupt the outfit’s composed narrative.