Located in the heart of Manhattan, the Upper East Side has long been synonymous with refinement, old-world charm, and sartorial excellence.
This bastion of taste, stretching from 59th Street to 96th Street, east of Central Park, has cultivated a distinctive style that resonates with discerning gentlemen worldwide.
As we delve deeper into the nuances of Upper East Side style, we’ll explore how these elements come together to create a look that’s at once timeless and relevant, steeped in history yet perfectly at home in the modern world.
Whether you’re a resident of this storied neighbourhood or admire its sartorial traditions, this guide will provide you with the knowledge to embrace and embody the essence of Upper East Side style.
What is the Upper East Side Style
Upper East Side style is not merely a fashion choice; it’s a sartorial philosophy rooted in the concept of Old Money aesthetic.
This term, far from being a mere financial descriptor, encapsulates a set of values: understated elegance, quality craftsmanship, and a deep respect for tradition.
The Upper East Side gentleman dresses not to impress but to express a heritage of taste cultivated over generations.
The Origin
The origins of this distinctive style can be traced back to the Gilded Age, when families like the Vanderbilts and Astors established the Upper East Side as New York’s most prestigious address.
These industry scions brought a European-influenced aesthetic, characterised by impeccable tailoring and a penchant for subtle luxury.
As the 20th century progressed, this style evolved, incorporating elements of American sportswear while maintaining its core ethos of refined understatement.
Upper East Side vs Ivy League
While often compared to Ivy League Preppy style, Upper East Side fashion stands apart in its sophistication and restraint.
Where Ivy style embraces youthful exuberance and sometimes playful elements, the Upper East Side style leans towards a more mature, polished look. Think of it as the distinguished elder statesman to Ivy’s energetic young graduate.
The WASP Roots
The Upper East Side aesthetic also shares commonalities with WASP (White Anglo-Saxon Protestant) style, particularly in its appreciation for tradition and quality.
However, it distinguishes itself through a more cosmopolitan outlook, influenced by New York’s status as a global fashion capital.
Upper East Side and the British Aristocrats
Perhaps the closest sartorial cousin to the Upper East Side style is British aristocratic fashion, as both share a reverence for bespoke tailoring, fine fabrics, and timeless designs.
However, the Upper East Side style incorporates a uniquely American stylistic flavour, balancing Old World refinement with New World dynamism.
Upper East Side Wardrobe Essentials
| Category | Items | Significance |
|---|---|---|
| Suits | Custom tailored suits, Navy blazer | Symbol of refinement, wardrobe functional piece. |
| Shirts | Custom dress shirts, OCBDs | Essential for both formal and casual wear |
| Trousers | Wool dress trousers, Chinos | Complement to suits or separates |
| Outerwear | Cashmere overcoat, Trench coat | Practical luxury, weather protection with style |
| Footwear | Oxford shoes, Loafers, Brogues | Traditional footwear for different occasions |
| Accessories | Silk ties, Pocket squares, Fine watches | Subtle indicators of taste and attention to detail |
Suits
The Upper East Side style of suit is a masterpiece of tailoring, custom-made by renowned establishments like Martin Greenfield Clothiers.
These tailored suits use fabrics from prestigious mills such as Loro Piana and Vitale Barberis Canonico, guaranteeing unmatched quality and longevity.
The quintessential Upper East Side suit features a two-button, single-breasted jacket with notch lapels, embodying timeless sophistication.
Fine wool patterns, such as chalk or rope pinstripes and grey or navy glen plaids, add subtle elegance without overwhelming the senses.
Every aspect of these suits, from the precise cut to the luxurious fabrics, reflects the wearer’s refined taste and attention to detail.
The navy blazer is another indispensable garment in the Upper East Side wardrobe. Crafted from high-quality hopsack wool, it has the perfect blend of breathability, texture, and sharp appearance.
Moreover, when adorned with brass or mother-of-pearl buttons, it can transition seamlessly from boardroom meetings to weekend luncheons in the Hamptons, epitomising the Upper East Side’s effortless fusion of formal and casual styles.
Shirts
In the Upper East Side style, custom dress shirts from elite shirtmakers like Charvet and Turnbull & Asser set the standard and form the foundation of every outfit.
These shirts are crafted from the finest Sea Island or Egyptian cotton, renowned for their long staple fibres that produce unparalleled softness and durability fabric.
The fit is immaculate: the shirt skims the body without clinging, and the sleeves end precisely at the wrist bone.
Meticulous details such as single-needle stitching, mother-of-pearl buttons, and side seam gussets elevate these shirts to the realm of wearable art.
For less formal occasions and available in white, light blue, and subtle stripes, the Oxford Cloth Button-Down (OCBD) stands supreme.
Originating from Brooks Brothers in the late 19th century, the OCBD has become an icon of American prep style, fully embraced by the Upper East Side.
The distinctive roll of the button-down collar, achieved through precise construction and interfacing, is the hallmark of a quality OCBD and encapsulates the Upper East Side’s appreciation for craftsmanship.
Trousers
Tailored trousers are a non-negotiable part of any Upper East Side outfit, whether worn as part of a suit or separately.
For formal occasions, fine wool trousers with flat fronts are the norm, as pleats are considered outdated in Upper East Side circles.
The trouser break is minimal, with the hem touching the shoe, creating a clean, elongated silhouette showcasing meticulous attention to detail.
Grey flannel trousers, a staple of the Upper East Side since the Duke of Windsor popularised them in the 1930s, reign supreme in cooler months.
Their soft, brushed surface adds subtle texture and pairs equally well with worsted jackets and chunky knit sweaters.
For casual wear, Upper East Siders choose high-quality chinos, a far cry from department store varieties.
These trousers are meticulously crafted from dense, tight-weave cotton twill and feature refined details like side-tab adjusters instead of belt loops.
Available in classic shades of khaki, navy, and olive, these chinos represent a sophisticated approach to casual wear, suitable for city weekends and coastal day trips.
Outerwear
The Upper East Side approach to outerwear blends practicality with understated luxury, reflecting the wearer’s sophisticated taste and lifestyle.
The classic cashmere overcoat in navy, charcoal, or camel is a cornerstone of every Upper East Side wardrobe.
These coats, sourced from heritage brands like Loro Piana or Brunello Cucinelli, offer unparalleled warmth and softness while maintaining a sleek silhouette.
The styling is intentionally minimalist, with clean lines and subtle detailing, allowing the superior quality of the material to speak for itself.
For rainy days, reach for the iconic trench coat, with Burberry and Aquascutum being the preferred choices.
These coats, in classic beige or navy, feature traditional elements like epaulettes, storm flaps, and a belt, serving both functional and aesthetic purposes.
The length falls below the knee, providing ample coverage while maintaining a sharp, tailored look synonymous with Upper East Side style.
In casual settings, during weekend getaways to the Hamptons or New England, quilted jackets are the outerwear of choice.
Brands like Barbour, known for their waxed cotton jackets, are favoured for their rugged practicality and understated elegance.
In olive or navy, these jackets pair effortlessly with Upper East Side staples, from OCBDs and chinos to cable-knit sweaters and corduroys, embodying the versatile nature of Upper East Side casual wear.
In the Upper East Side style, footwear is characterised by exceptional quality, fine craftsmanship, and timeless design.
For formal occasions, the black cap-toe Oxford reigns supreme, handcrafted by renowned shoemakers like John Lobb or Edward Green.
In business settings, dark brown brogues or semi-brogues are popular choices. Their perforations and decorative elements add visual interest without sacrificing elegance.
Alden and Crockett & Jones are favored brands known for their exceptional quality and traditional styling that aligns with Upper East Side sensibilities.
Penny loafers and tassel loafers in rich burgundy or dark brown shades are an Upper East Side staple for smart casual occasions.
These slip-on shoes strike the perfect balance between formal and relaxed, embodying the elegant sophistication of the Upper East Side style.
Belgian shoes, with a distinctive bow and incredibly soft leather, are another Upper East Side favourite for casual wear.
In warmer months, especially for weekend events, suede driving moccasins or boat shoes in navy, tan, or chocolate brown are the norm, demonstrating the Upper East Side’s knack for elegant looks even in casual settings.
Accessories
In the Upper East Side style, accessories are chosen carefully to complement rather than overshadow the ensemble.
Silk neckties feature subtle patterns like repp stripes, small geometrics, or foulards.
Brands such as Hermès and Marinella are highly regarded for their quality and design.
The four-in-hand knot is the preferred style, tied with understated elegance and dimpled just below the knot.
Pocket squares must be made of silk or linen, with hand-rolled edges, to signify high quality and coordinate with the ties, but they must not be a perfect match.
Watches are selected for their refinement rather than ostentation, with brands like Patek Philippe, Vacheron Constantin, or A. Lange & Söhne favoured their understated luxury and horological significance.
When worn, cufflinks are simple and elegant, crafted in sterling silver or yellow gold, and ideally encrusted with family crests or subtle monograms.
Leather goods, including wallets and briefcases, come from high-quality brands like Valextra or Smythson, known for their exceptional craftsmanship and discreet branding.
Upper East Side Style Rules
To truly understand and embody the Upper East Side style, you must grasp the look’s fundamental principles.
These pillars form the bedrock upon which this New York Old Money aesthetic is built.
| Pillar | Key Attributes |
|---|---|
| Perfect Tailoring | Bespoke craftsmanship, impeccable fit, subtle structural details |
| Quality Materials | Fine wools, Sea Island cotton, cashmere, silk |
| Silent Luxury | Subtle brand markers, emphasis on craftsmanship over logos |
| Classic Silhouette | Timeless cuts, enduring styles, resistance to fleeting trends |
| Subtle Detail | Hand-finished motifs, precise accessorising, rare patterns |
Manhattan’s Upper East Side Outfit Ideas by Season
Spring Outfit Idea
Start with a light grey suit in tropical wool from Loro Piana, a sky-blue cotton shirt, and a pale yellow silk tie to add a subtle nod to the season.
Wear brown suede loafers and a matching belt, and complete the look with a lightweight trench coat in classic beige as outerwear to be ready for the unpredictable spring weather.
Summer Outfit Idea
Start with a navy blue blazer in a breathable hopsack weave, crisp white linen trousers, and a soft pink cotton shirt with an open collar.
Wear leather penny loafers without socks and accessorise with a silk pocket square in a subtle floral pattern that adds a seasonal flair.
Autumn Outfit Idea
As leaves turn, the Upper East Side style turns to richer textures.
Start with a charcoal flannel suit paired with a light blue oxford cloth button-down shirt and a burgundy knit tie.
Wear dark brown cap-toe oxfords and a matching belt, and complete the outfit with a camel hair polo coat draped over the shoulders.
Winter Outfit Idea
Start with a navy chalk stripe suit in heavy wool layered over a white shirt with French cuffs.
Wear black Oxford shoes and a black leather belt, and accessorise with an ancient green Madder silk tie and gold cufflinks.
Finish the look with a charcoal cashmere overcoat and a grey cashmere scarf.
Upper East Side Style Do’s and Don’ts
Do
- Invest in bespoke suits from renowned tailors like Martin Greenfield or Huntsman, focusing on classic cuts and fabrics like Super 150s wool.
- Opt for custom-made shirts from brands like Charvet or Turnbull & Asser, ensuring precise collar and cuff fits.
- Choose a subdued colour palette dominated by navy, charcoal, and earth tones for suits and jackets.
- Maintain a weekly grooming routine, including professional haircuts every 3-4 weeks and regular manicures.
- Invest in a high-quality shoe care kit and polish your shoes at least twice weekly.
- Have trousers hemmed with a slight break, just touching the top of your shoe.
- Wear pocket squares that complement but don’t exactly match your tie.
- Choose understated, high-end watches from brands like Patek Philippe or A. Lange & Söhne.
- Use collar stays to maintain crisp shirt collars throughout the day.
- Opt for classic patterns like subtle pinstripes, small checks, or herringbone in suiting.
Don’t
- Wear clothing with visible logos or branding, even from luxury brands.
- Purchase or wear fast-fashion items, regardless of current trends.
- Neglect shoe trees or proper shoe rotation – use cedar shoe trees and never wear the same pair two days in a row.
- Wear shorts, sandals, or athletic wear outside of appropriate sporting venues.
- Combine more than three patterns in a single outfit.
- Wear pre-tied bow ties – always tie your own.
- Use belt and shoe leather colours that don’t match exactly.
- Wear socks that don’t extend above your calf when seated.
- Button the bottom button of your suit jacket or waistcoat.
- Wear novelty ties or cufflinks, even for festive occasions.
- Use strongly scented colognes – opt for subtle, classic fragrances instead.
- Wear loafers with formal business suits.
- Leave visible wrinkles or creases in your clothing – invest in a quality iron and learn to use it properly.
- Wear brown shoes after 6 pm for formal occasions in the city.
- Use synthetic fabrics for suits, shirts, or ties – always opt for natural fibres.
Conclusion
Upper East Side style is more than just a fashion choice; it’s a lifestyle that values quality, tradition, and understated elegance.
Every component of this style speaks to a commitment to refinement and attention to detail, from the perfectly tailored suit to the carefully chosen accessories.
Whether dressing for a board meeting, a charity gala, or a weekend in the Hamptons, the Upper East Side gentleman always presents himself with poise and sophistication.
The Upper East Side style is not about following fast-fashion trends but creating a bespoke wardrobe with classic and timeless garments depicting silent luxury, wealth, and success.
