What to Wear in the Hamptons: Summer 2025 Guide

Table of Contents

1. The Cultural Landscape: Hamptons 2025

2. Geographic Literacy: Navigating "The Hams"

3. Daytime Essentials: When Casual Isn't Really Casual

4. Evening Evolution: After the Sun Sets

5. The Technical Artistry: Fabrics That Define the Season

6. The Tailoring Advantage: Structure Meets Comfort

7. LVIS: The East Hampton Fashion Archive

8. The Weekend Warrior: Friday to Sunday Transformation

9. The Unwritten Rules: Style Beyond the Garments

10. Cultural Literacy: Pop References Worth Knowing

11. Municipal Navigation: Townships, Regulations, and Social Customs

12. Final Notes: Dressing with Intention

The Cultural Landscape: Hamptons 2025

Around The Tailory NY we refer to the Hamptons as The Hams. People love it when they hear it. This summer scene exists where Manhattan money meets maritime aesthetics—creating a specific type of social environment with its own rules.

Don't say Hamptons. Be specific and pronounce the locales properly. Southampton is one word, it contains a direction and AMPton, heavy emphasis on AMP-ton, it isn't South Hampton. Quiogue is pronounced KWY-AUG, this isn't the Jersey Shore, so keep up.

Act like you have been there before and remember that the real Hamptonites are there as an escape, they don't want to see their friends from Greenwich Street, or take in vibes created by Citiots (City Idiots) that act in any outdoor space like they are in Union Square. You're not there to operate like you do on Hudson Street, you're there for a getaway, getting away from the City, and the people you co-habitate with.

Drive like you are enjoying a country drive. Don't text or make calls, don't even have your phone in sight for bystanders to see. The Hamptons are a vacation from your home and social media as much you being there for the beach and fresh air.

For Summer 2025, we're seeing a shift away from last year's excess toward something more restrained. Not minimalist, not austere, but more controlled. This studied casualness actually requires more thought than most people realize.

Geographic Literacy: Navigating "The Hams"

Laser pointer geography is a must, don't reference the North Fork as anything but the North Fork, it has no relativity to the South Fork (the Hamptons). Shelter Island isn't in the Hamptons, it's an island between the forks with as much quality as the Hams. Bridgehampton is the bridge between Sagaponack and Sag Harbor.

There are only 2 townships: Southampton and East Hampton important to know since the municipalities have a heavy hand in all aspects. Both townships enforce the single family law: only one family can reside in a 1-family house, so invite your Aunties, cousins, etc if you want a stressful time when you should be focusing on being stress-free.

Bring cash for roadside attractions. The sophisticated visitor recognizes that some of the most authentic East End experiences occur outside the digital payment infrastructure.

Daytime Essentials: When Casual Isn't Really Casual

The Hamptons daytime uniform remains a study in calculated nonchalance—like those early Friends episodes where Rachel Green's "just threw this on" look required three hours of preparation.

For those presenting in more masculine silhouettes, consider:

• Linen suiting and casuals provide the breathable structure needed for balancing comfort with presentation

• Seersucker suiting offers classic appeal with contemporary relevance

• Bamboo suiting and casuals deliver sustainability with sophisticated drape

For those drawn to feminine-coded options:

• Wide-leg linen trousers with precise pleating

• Cotton-bamboo blend dresses with thoughtful construction

• Form-tailored shorts with matching overshirts

• Lightweight seersucker pieces that maintain structure throughout the day

Boat shoes have never and won't ever be in style. Their persistent presence represents fashion's version of a participatory trophy—awarded not for excellence but mere existence.

Hats that old men wear while fishing is never a good look. The sophisticated alternative? Structured Panama hats with moderate brims or, for the genuinely minimalist, no hat at all.

Be more concerned about what to wear in the yard when your grilling rather than going to restaurants because everyone knows that the restaurants in the Hamptons suck. The most memorable evenings happen in private gardens and on screened porches, where the host's effortless style matters far more than being seen at the right establishment.

Evening Evolution: After the Sun Sets

Hamptons evening wear for 2025 coalesces disparate influences into something distinctive—the structured minimalism of late '90s Calvin Klein married to the technical innovation of current Japanese designers, with a whisper of Studio 54 glamour.

For masculine-presenting wardrobes:

• Unstructured seersucker jackets reimagined with contemporary proportions—slimmer lapels and strategic darting that honors the fabric's heritage while avoiding its caricature

• Pleated linen trousers with considered proportions—neither billowing nor compressed, hemmed to create a clean break atop Belgian loafers or minimal leather footwear

• Fine-gauge bamboo knits that negotiate the evening temperature drop while maintaining shape, offering the comfort of a t-shirt with the structure of more formal options

• Tonal dressing that creates cohesion without monotony, navy layered with indigo rather than punctuated with contrast, creating visual depth through texture rather than color

For feminine-presenting options:

• Architectural linen-silk blend separates that transform cocktails into occasions, structured to create intentional silhouettes rather than surrendering to fabric properties

• Technical silk that accommodates the maritime humidity without surrendering structure, processed to resist both wrinkling and environmental damage

• Precisely tailored bamboo-blend jumpsuits that convert from dining to entertaining at home, eliminating the need for wardrobe changes during evenings that evolve organically

• Monochromatic ensembles with textural interplay instead of color contrast, drawing sophistication from subtle variation rather than obvious statement

The evening palette has settled into controlled exuberance—navy that reads almost black, olives with unexpected depth, and whites that carry undertones of sand or shell rather than clinical brightness. This spectrum functions like those perfectly curated mixtapes from the analog era—each element distinct yet contributing to a cohesive whole.

And here's the essential secret: be more concerned about what you're wearing while grilling in your yard than about restaurant attire. Everyone who matters knows the restaurants in the Hamptons have become exercises in mediocrity disguised by prohibitive pricing. The most memorable evenings happen in private gardens and on screened porches, where the host's effortless style matters far more than being seen at the right establishment.

The sophisticated approach to evening dress acknowledges that the most significant Hamptons moments occur in residential rather than commercial contexts. This means prioritizing comfort while maintaining structure, accounting for temperature variations that can shift dramatically after sunset, and considering the practical realities of environments that shift between indoors and outdoors throughout the evening.

The Technical Artistry: Fabrics That Define the Season

Summer in the Hams requires the right fabrics. Here's what works:

Structured Linen Modern linen holds its shape better than the rumpled versions of the past. Good linen feels substantial without being stiff and maintains some structure even after sitting in it for hours.

Seersucker Reimagined Forget the blue and white stripes worn by Southern politicians. Today's seersucker comes in subtle patterns and sophisticated colors. Look for tonal blues or monochromatic versions that provide the cooling effect without the costume feel.

Bamboo Blends Bamboo is the perfect summer fabric - it regulates temperature, has natural moisture-wicking properties, and drapes beautifully. Find it in polos, casual shirts, and even unstructured jackets.

Technical Naturals Natural fabrics with minimal technical enhancements work best. Think cotton with a touch of stretch or linen with moisture-wicking properties. These maintain the look of natural fabrics with added performance.

The Tailoring Advantage: Structure Meets Comfort

Custom tailoring makes all the difference in summer fabrics. The Tailory NY focuses on several key elements:

Proportional Precision Summer clothing needs different proportions than winter wear. Jacket lengths, sleeve pitch, and trouser breaks all need adjustments for lightweight fabrics. A properly tailored summer garment looks intentional, not like you bought something off the rack and hoped for the best.

Strategic Deconstruction Good summer tailoring removes unnecessary structure while keeping what matters. This means lighter shoulder construction and minimal chest pieces, but with enough internal architecture to maintain shape. The result feels weightless but looks deliberate.

Personalized Fitting Summer fabrics reveal fit issues more obviously than winter clothing. Every body has different proportions, posture, and movement patterns. Custom fitting accounts for these differences, ensuring linen trousers break correctly at the shoe and seersucker jackets follow your body's actual contours.

Intentional Ease The most sophisticated summer garments incorporate the right amount of room in the right places. This creates the difference between looking relaxed and looking rumpled. The goal is controlled comfort, not shapelessness.

LVIS: The East Hampton Fashion Archive

The Ladies' Village Improvement Society thrift shops at 95 Main Street represent perhaps the most authentic sartorial time capsule in East Hampton—a living museum where previous iterations of seasonal style await rediscovery by the discerning eye. Open Tuesday through Saturday from 10 AM to 5 PM, these unassuming spaces offer a fascinating counterpoint to current retail offerings.

Beyond merely serving as a source for budget-friendly beach attire, LVIS provides several distinctive advantages for the sophisticated dresser:

• Authentic Patina: Their racks offer genuinely sun-faded navy and red garments that have achieved the complex hues luxury brands attempt to manufacture artificially. What began as vibrant crimson shorts have weathered through actual Hamptons wear into that impossible-to-replicate salmon that signals genuine provenance.

• Adaptation Resources: For those experiencing sudden size fluctuations (whether Ozempic-induced or simply the result of vacation indulgence), LVIS provides affordable transitional pieces from their constantly refreshed inventory. This practical consideration acknowledges the reality of body changes without judgment or excessive investment.

• Styling Research: Examining how garments from different eras have responded to the specific conditions of East Hampton provides invaluable insight for contemporary design. The evolutionary history of how fabrics interact with sand, salt, and sun creates a material education that transcends theoretical knowledge.

• Sustainability Statement: Repurposing these pieces demonstrates environmental consciousness without conspicuous virtue signaling. The most sophisticated approach to sustainability involves extending the lifecycle of existing quality garments rather than purchasing newly manufactured "eco-friendly" options.

• Community Investment: Revenue from purchases directly funds LVIS community improvement projects, creating a virtuous circle of local engagement. This transforms consumption from mere acquisition into community participation—a distinction that matters in contexts where social involvement carries currency.

The most sophisticated approach involves strategic integration—perhaps pairing a meticulously tailored contemporary linen jacket with a perfectly faded LVIS vintage tee, creating a dialogue between past and present that demonstrates genuine cultural fluency rather than trend-chasing.

The slightly off-white sweaters with faded horizontal stripes serve as stealth signals of insider status, communicating a deeper understanding of East End authenticity than any logo-emblazoned designer piece ever could. Similarly, those legendary faded red (now salmon) shorts and the navy counterparts that have achieved the perfect fade represent authentic Hamptons heritage impossible to simulate through artificial distressing.

Remember to bring cash for these analog shopping experiences, just as you would for the farm stands and roadside attractions that represent the authentic East End experience. Digital convenience is occasionally worth sacrificing for analog authenticity, particularly when it provides access to the genuine article rather than its mass-produced simulation.

The Weekend Warrior: Friday to Sunday Transformation

The Hamptons weekend demands a sartorial narrative arc that parallels the three-act structure of classic films—arrival establishes character, Saturday builds tension, Sunday resolves with contemplative preparation for re-entry into Monday reality.

Friday: The Arrival Friday arrival calls for transitional pieces that acknowledge both the office left behind and the leisure ahead:

• Tailored travel wear that resists wrinkling while projecting intention, constructed from technical fabrics that maintain structure despite hours in transit

• Versatile layers that can be reconfigured as the day's demands shift, accommodating both remaining work obligations and initial social engagements

• Footwear that navigates both urban departure points and coastal arrival, designed for the specific movement patterns of travel rather than mere aesthetics

The Friday evening transformation requires calculated efficiency:

• Pieces that convert from travel to social contexts with minimal adjustment

• Structured casualwear that acknowledges the liminality of Friday evening—neither fully weekend nor fully workweek

• Accessories that signal the transition from professional to personal contexts

Saturday: The Full Expression Saturday represents the narrative climax of Hamptons performance, requiring:

• Morning athleisure with technical precision for tennis, golf, or strategic beach positioning—garments that perform genuinely athletic functions while maintaining aesthetic coherence

• Afternoon transition pieces that accommodate impromptu social encounters, designed to manage both planned and unplanned engagements

• Evening statement pieces that communicate serious leisure as effectively as Madonna reinvented herself between albums—garments that perform rather than merely decorate

The Saturday wardrobe requires strategic planning:

• Multiple complete outfits that anticipate environmental and social variability

• Technical pieces that accommodate active engagements without sacrificing structure

• Evening options that balance comfort with presentation, acknowledging that the most significant Hamptons moments often occur in residential rather than commercial contexts

Sunday: The Denouement Sunday brings the denouement—comfort without surrender:

• Softly structured pants with technical waistbands that accommodate weekend indulgence, designed with the awareness that Sunday bodies often differ from Friday bodies

• Layered separates prepared for both lingering and departure, acknowledging the uncertainty of Sunday schedules

• Accessories that reference the weekend while anticipating re-entry, creating psychological transition alongside physical relocation

The Sunday approach requires particular nuance:

• Garments that manage the psychological transition back to urban contexts

• Pieces that accommodate the inevitable rush of departure without sacrificing structural integrity

• Silhouettes that maintain weekend ease while beginning to reintroduce workweek structure

For the spontaneous Hamptons visitor or those experiencing sudden wardrobe malfunctions (or Ozempic-induced size fluctuations), LVIS shops serve as essential fashion first responders, open Tuesday through Saturday from 10 AM to 5 PM. Their constant rotation of donations ensures fresh options for navigating unexpected social invitations or beach days.

The sophisticated weekend warrior understands that Hamptons dressing involves narrative coherence rather than disconnected statement pieces—each day building upon the previous while anticipating the next, creating a comprehensive story rather than a series of isolated incidents.

The Unwritten Rules: Style Beyond the Garments

True Hamptons style extends beyond clothing to encompass behavior, accessories, attitude, and transportation choices—all of which communicate fluency in the unwritten codes of the East End.

The Hampton Jitney: Transit as Performance

The Hampton Jitney—that distinctive coach service connecting Manhattan to the East End—serves as both transportation necessity and social microcosm. This rolling antechamber to the Hamptons experience functions as the first stage upon which your East End fluency is evaluated, making your Jitney presentation almost as significant as your eventual destination appearance.

The sophisticated Jitney passenger maintains several essential principles:

Dressed for Destination, Not Journey Despite the bus-like conveyance, this isn't public transportation in the conventional sense. The Jitney wardrobe should telegraph where you're headed rather than acknowledging where you are. This means:

• Lightweight layers that accommodate both NYC departure heat and Hamptons arrival breeze

• Tailored separates that resist wrinkling during the journey while maintaining structural integrity

• Footwear that slips on and off easily at your seat while still complementing your overall look

• Strategic accessories that multitask—scarves that serve as both style elements and impromptu pillows, totes that organize essentials while communicating taste

The Tailory NY's travel-specific pieces prove invaluable here—technical fabrics that maintain shape despite hours in transit, strategically structured garments that resist compression creasing, and proportions calculated to look appropriate both seated and standing.

Behavioral Choreography The Jitney code extends beyond mere clothing to encompass specific behavioral expectations:

• Board as if entering a business colleague's home—efficiently, quietly, without unnecessary ceremony

• Maintain library-appropriate conversational volume, regardless of your traveling companions' size

• Treat the attendant with the respect their position demands, not as service staff but as the guardian of Jitney decorum

• Prepare exact change for any onboard purchases rather than creating payment complications

• Never, under any circumstances, remove shoes—regardless of journey length or personal comfort

The Electronic Etiquette Phone usage on the Jitney requires particular restraint:

• Treat the Jitney as a technological decompression chamber—begin reducing screen time as preparation for proper Hamptons disengagement

• Understand that visible phone usage signals commuter rather than weekender status

• If work necessitates device use, employ the minimalist approach—small screens, discreet movements, reduced brightness

• Recognize that the most sophisticated Jitney passengers appear to have forgotten technology exists altogether

The Strategic Seat Selection Where you sit communicates volumes about your Hamptons relationship:

• Ambassador seats suggest confidence and regular ridership

• Mid-coach positioning indicates social awareness without status anxiety

• Rear section seating, particularly without reservation, signals Jitney novice status

• The most sophisticated riders appear mysteriously content regardless of their assigned position

The Jitney journey, when approached correctly, serves as more than mere transportation—it functions as a transitional ritual that prepares you mentally for the shift from urban intensity to coastal selective leisure. The Tailory NY understands this liminality, creating transition wardrobes that bridge these worlds without compromising either structural integrity or style intelligence.

Eyewear Intelligence

Sunglasses should fit your face first and follow trends second. The most egregious eyewear error involves choosing frames based solely on designer cachet or current popularity without considering how they interact with your specific facial architecture. Instead, identify styles that balance and complement your features—whether that means classic aviators or contemporary geometric frames.

Sophisticated eyewear selection involves:

• Understanding that shape compatibility trumps brand identity

• Recognizing that proper fit involves multiple contact points rather than merely aesthetic appeal

• Selecting optical quality that genuinely protects vision rather than merely obscuring it

• Choosing styles appropriate to specific activities rather than generic options

Behavioral Grooming You're not on Hudson Street anymore. The sophisticated visitor understands that the Hamptons represent a departure from urban pace and behavior. Drive like you're enjoying a country excursion rather than racing to the next meeting. Keep your phone tucked away rather than performatively checking it poolside. These behavioral choices constitute a form of social styling as significant as your garment selection.

Essential behavioral adjustments include:

• Leaving aggressive urban driving habits at the Midtown Tunnel—the roads here aren't meant for Manhattan pacing

• Keeping your phone out of sight for bystanders—nothing screams "visitor" more clearly than constant device checking

• Recognizing that you're there for a getaway, both physically and metaphorically, from the city and its inhabitants

• Understanding that the people who seem unfazed by everything are likely the ones who actually belong

Transportation Aesthetics The vehicle you drive communicates as much as what you wear. The classic Jeep Wagoneer with wood paneling or vintage Land Rover Defender makes a different statement than this year's flashiest Italian sports car. Consider how your transportation choices align with the understated elegance that defines authentic Hamptons presence.

Vehicular considerations include:

• Recognizing that understated durability trumps flashy performance in this context

• Understanding that vintage utility signals belonging more effectively than contemporary luxury

• Considering the practical requirements of beach access and unpaved roads

• Keeping vehicles clean but not obsessively detailed—suggesting actual use rather than mere display

Cash Culture Bring actual currency for roadside stands, impromptu farm purchases, and other local commerce that still operates in the analog world. The sophisticated visitor recognizes that some of the most authentic East End experiences occur outside the digital payment infrastructure. This practical preparation signals respect for local traditions and businesses.

Contextual Awareness Different locations within the East End demand subtle stylistic adjustments. Montauk's surfing heritage permits a more relaxed approach than Southampton's old-money reserve. Fine-tuning your wardrobe selections to acknowledge these micro-regional distinctions demonstrates true insider knowledge rather than tourist approximation.

Remember that genuine Hamptonites are there seeking respite from the city's social obligations. They don't want their sanctuary infiltrated by the same dynamics they've temporarily escaped. The most sophisticated style strategy involves appearing completely at ease—as if you belong precisely where you are, without needing to announce or justify your presence.

Cultural Literacy: Pop References Worth Knowing

Understanding the Hamptons requires awareness of how the region has been portrayed in popular culture—both accurately and misleadingly. These cultural touchpoints provide valuable context for navigating the actual experience.

Seinfeld's East Hampton Episode The Seinfeld episode where Jerry and friends venture to East Hampton offers a surprisingly insightful examination of insider/outsider dynamics in "The Hams." The episode's iconic moments—George's "shrinkage" incident in the cold pool water, the much-discussed Hamptons tomatoes, Jane sunbathing topless on the beach, Kramer poaching lobster traps, the family doctor describing everything from ugly babies to beautiful women as "breathtaking," and Jerry's observation that facing the wrong way on the train makes you feel like you're going back in time—all reflect authentic Hamptons experiences filtered through the show's satirical lens.

While played for comedy, the episode captures something authentic about the tension between casual appearance and behavioral expectations, as well as the subtle social barriers that remain invisible until inadvertently crossed. Anyone who has experienced both the social promise and anxieties of East Hampton weekends recognizes the truth beneath the exaggeration.

The episode serves as a reminder that:

• Even in casual contexts, unwritten rules govern behavior

• Appearing to belong often matters more than actual belonging

• Social miscalculations can transform seemingly minor incidents into significant breaches

• The most insurmountable barriers are those you don't initially recognize as barriers

• What you wear (or don't wear) on a Hamptons beach communicates far more than mere style preference—it signals your understanding of context-specific social codes

This classic sitcom segment mirrors the experience of wearing an impeccably tailored yet seemingly casual garment—beneath the appearance of effortlessness lies careful construction and precise calculation. The Tailory NY understands this principle intimately—creating pieces that appear unstudied yet require meticulous craftsmanship, much like the social performances that define successful Hamptons integration.

Something's Gotta Give Something's Gotta Give presents the aspirational Hamptons aesthetic—those impeccably appointed beach houses with their neutral palettes and calculated casualness. The plot follows Jack Nicholson as a sugar daddy who suffers a panic attack, ends up in the hospital, and subsequently rehabs at Diane Keaton's Hamptons home—a recovery period that transforms him into someone capable of age-appropriate romance. Keanu Reeves and Diane Keaton deliver equally memorable performances in this film that, while romanticizing the setting, captures something authentic about the architectural and design sensibilities that inform the region's aesthetic values.

The film's visual language demonstrates:

• How neutral palettes create sophisticated backdrops for both socializing and solitude

• The calculated balance between comfort and presentation in residential spaces

• The integration of natural materials that reference rather than merely imitate the coastal environment

• How casual elegance emerges from thoughtful curation rather than conspicuous consumption

• The essential Hamptons fantasy—a place where even the most superficial characters eventually discover authentic connections, much like how properly tailored clothing reveals rather than disguises the wearer's true self

Pathetic TV Misrepresentations Shows like Revenge and Royal Pains offer cartoonish misrepresentations of Hamptons life—useful primarily as examples of what actual Hamptons experience isn't. These portrayals emphasize manufactured drama and visual clichés rather than the subtle social dynamics that characterize authentic East End life.

These shows serve as unintentional guides for what to avoid:

• Obvious displays of wealth that signal insecurity rather than confidence

• Manufactured confrontations that violate the unwritten code of discretion

• Stereotypical "Hamptons" activities that exist primarily in television writers' imaginations

• Clothing and accessory choices that prioritize visibility over appropriateness

The sophisticated visitor recognizes the distinction between media portrayal and lived reality, understanding that authentic Hamptons experience often involves precisely what these shows exclude—quiet afternoons, understated gatherings, and genuine appreciation of the natural environment rather than merely its social opportunities.

Municipal Navigation: Townships, Regulations, and Social Customs

Understanding the governmental structure of the Hamptons proves essential for both practical navigation and social fluency. The region operates under a distinctive regulatory framework that shapes everything from housing arrangements to beach access.

Township Structure The Hamptons comprises two primary townships—Southampton and East Hampton—each with its own government, regulations, and enforcement priorities. This distinction matters beyond mere trivia, as these municipalities exercise significant control over daily life and seasonal activities.

Key township considerations include:

• Beach access regulations that vary between townships and even between specific beaches

• Noise ordinances that determine when and where social gatherings can occur

• Parking restrictions that can transform a simple outing into a logistical nightmare

• Conservation regulations that protect the natural environment while sometimes limiting recreational options

The Single-Family Housing Regulation Both Southampton and East Hampton have single-family housing regulations—technically, only one family can legally reside in a single-family house. Of course, you can go with 15 people to a big house and all stay there like it's the Jersey Shore—but why would you want to? Extended family can certainly stay with you, but aunties, cousins, and other relatives create unnecessary stress during a period meant for relaxation.

Practical implications include:

• Understanding that the Hamptons vacation ethos is about quality, not quantity of companions

• Recognizing that packing a house with extended family defeats the purpose of a sophisticated escape

• Acknowledging that what might seem like a fun group gathering often transforms into logistical complications

• Remembering that you came to the East End to escape, not to recreate the same social dynamics you left behind

Social Customs and Expectations Beyond formal regulations, unwritten social customs govern Hamptons interaction. These evolved traditions often carry more weight than official rules, particularly in long-established communities.

Essential social knowledge includes:

• Understanding the distinction between year-round residents and seasonal visitors

• Recognizing the hierarchical relationship between property owners and renters

• Acknowledging the complex dynamic between service providers and clients

• Respecting the distinctive social patterns of specific communities within the larger Hamptons context

The Hamptons represent a departure from urban social patterns in significant ways. Noise that might go unnoticed in Manhattan becomes disruptive in residential Hamptons settings. Social circles that overlap seamlessly in city contexts maintain careful separation in East End environments. The sophisticated visitor recognizes these distinctions and adjusts behavior accordingly, understanding that social currency in one context doesn't necessarily transfer to another.

Final Notes: Dressing with Intention

The 2025 Hams season requires more than wearing the right labels. It demands understanding an unwritten code that extends beyond garments to behavior, geographic knowledge, and social awareness.

The Tailory NY's bespoke approach creates pieces that navigate these complex waters without obvious effort—garments that appear effortless precisely because every detail has been calculated. Custom tailoring ensures that summer-weight fabrics—from classic linen to innovative bamboo blends—maintain their intended lines throughout wear.

Don't say Hamptons without geographic specificity. Pronounce Southampton with proper emphasis on "AMP-ton." Bring cash for roadside stands. Wear sunglasses that fit your face and look cool, not ones that just look cool. Never, ever wear boat shoes.

Forget restaurants—focus on looking good while grilling in your own yard. Act like you've been there before. Drive like you're enjoying the countryside, not racing to a meeting. Put your phone away. Avoid fishing hats unless you're actually fishing.

This isn't fashion advice—it's an intelligence briefing. Consider yourself in the know. Treat this guide like it's a bible.

The rest is up to you.