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What’s This About

Upper East Side style is classic Manhattan tailoring with relaxed preppy weekends: navy blazers, grey flannel, Oxford shirts, navy and grey suits, trench coats and polished leather shoes.

This guide covers Upper East Side style for men, such as:

How the look differs from Ivy style and British tailoring

The suits, shirts and trousers to start with

Overcoats, trench coats and weekend jackets

Oxfords, brogues and loafers, and when to wear each

Four seasonal outfits for the city

and many more!

Fit, calm colours and care matter far more than labels or price.

Key Points

01The look combines city suits and blazers with relaxed weekend chinos, knitwear and loafers.

02Flat-front and pleated trousers are both classic; choose the one that fits and moves well.

03Loafers can work with suits, and a pocket square should complement the tie rather than match it.

04The clothes say nothing about where you live or what you earn; anyone can wear them.

Upper East Side style is a label for the classic tailored dressing associated with the Manhattan neighbourhood between 59th and 96th Streets, from Fifth Avenue to the East River.

In practice it means navy blazers, grey flannel trousers, Oxford shirts, well-fitted suits in navy and grey, trench coats and polished leather shoes, with relaxed preppy clothes at weekends.

You do not need to live there to wear it, and the clothes say nothing about anyone’s background or bank balance; fit, simple colours and care do the work.

This guide covers what the look is, how it differs from Ivy style, the wardrobe to build, four seasonal outfits and practical styling guidance.

What is Upper East Side style?

Upper East Side style is a city version of the old-money aesthetic: understated colours, natural cloth, good tailoring and few visible logos.

It is smart enough for an office or a gallery, but it relaxes at weekends into chinos, knitwear and loafers.

The photographs above show the range: navy blazers with coloured trousers, tweed jackets with knitted ties and double-breasted blazers with grey trousers.

Where the image came from

From the late nineteenth century, large private houses were built along Fifth Avenue north of 59th Street, and apartment buildings began replacing them from 1916.

That history gave the neighbourhood its formal reputation, and the clothes most associated with it today are classic American and British tailoring mixed with American sportswear.

Upper East Side style and Ivy style

Ivy League style uses many of the same garments, such as Oxford shirts, chinos, blazers and loafers.

Ivy outfits are usually more casual and collegiate, while Upper East Side outfits lean towards suits, ties and city overcoats.

Upper East Side style and British tailoring

The look also borrows from classic British style: flannel, tweed, chalk-stripe suits and brogues.

American details such as the button-down collar and the loafer keep it from looking like a copy of London dressing.

Upper East Side wardrobe essentials

Category	Garments	Why they are useful
Suits	Navy and grey suits, navy blazer	Cover work, dinners and events
Shirts	White and blue dress shirts, Oxford button-downs	Work with or without a tie
Trousers	Grey flannel, wool dress trousers, chinos	Pair with the blazer and with knitwear
Outerwear	Wool overcoat, trench coat, waxed or quilted jacket	Cover cold, rain and weekends away
Footwear	Black Oxfords, brown brogues, loafers	Range from formal to relaxed
Accessories	Silk ties, pocket squares, a simple watch	Add colour without logos

Suits

A navy or grey two-button, single-breasted suit with notch lapels is the core of the look.

Man in a brown suit, white shirt and striped tie leaning against a doorway — New York suits, New York, image courtesy of Drake’s

Our guide to the tailored suit explains the difference between made-to-measure, bespoke and altered ready-to-wear suits; good fit matters more than the method or the price.

Subtle chalk or rope stripes and grey or navy glen checks add interest without looking loud.

A navy blazer in hopsack wool, a breathable open weave, goes from a weekday meeting to a weekend lunch with grey trousers or chinos.

Shirts

White and light blue dress shirts with a collar that sits neatly under the jacket form the base of most outfits.

Man in a light blue shirt with white cuffs, paisley tie and beige chinos — Upper East Side style dress shirt with tie and chinos, image courtesy of @turnbull_asser // Instagram

Check that the shirt follows your body without clinging and that the cuff ends at the wrist bone.

For less formal days, the Oxford cloth button-down shirt in white, blue or fine stripes is the standard choice.

Man in a blue gingham button-down shirt, red chinos, brown belt and dark loafers — Upper East Side style outfit with Oxford shirt, New York, image courtesy of F. E. Castleberry

Brooks Brothers dates its button-down collar to an 1896 observation of polo players’ collars and to an introduction around 1900.

Trousers

Wool trousers come with a flat front or with pleats; both are classic, and pleats give more room in the seat and thigh.

Hem them to touch the top of the shoe with little or no break for a clean line.

Grey flannel trousers are a cold-weather staple, because the brushed cloth goes with worsted jackets, tweed and chunky knitwear.

Charcoal pleated flannel trousers with a black belt, striped knit and black lace-up shoes — Grey Flannel Trousers, image courtesy of Mr Porter

For casual days, choose dense cotton twill chinos in khaki, navy or olive; some have side adjusters instead of belt loops.

Two men in blazers and bow tie or tie, one in khaki chinos and one in pink chinos, outside a building — Upper East Side smart casual style chino outfit, New York, image courtesy of F. E. Castleberry

Outerwear

A plain wool or cashmere overcoat in navy, charcoal or camel covers the colder months.

Man in a navy double-breasted overcoat, flat cap, bow tie and burgundy trousers holding a leather folio — Upper East Side style overcoat outfit, New York, image courtesy of F. E. Castleberry

Keep the coat simple in line and detail, and check that it fits over a jacket.

For rain, a trench coat in beige, navy or black works over a suit; the design was developed as a British officers’ raincoat and named in the trenches of the First World War.

Man in a black knee-length raincoat over dark trousers and black shoes walking on a wet street — Upper East Side style trench coat outfit, New York, image courtesy of GQ

For weekends away, a waxed cotton or quilted jacket in olive or navy goes with Oxford shirts, chinos, cable-knit jumpers and cords.

Footwear

For formal occasions, black cap-toe Oxfords are the classic choice; John Lobb is one of many makers of this style.

Black cap-toe Oxford shoe worn with dark trousers and grey socks — Black cap-toe Oxford shoes, image courtesy of @johnlobb // Instagram

Dark brown brogues or semi-brogues work with grey and navy suits for business and with flannel trousers.

Dark brown leather wingtip brogues with blue patterned socks and white trousers — Dark brown brogues, image courtesy of Crockett & Jones

Penny loafers and tassel loafers in dark brown or burgundy suit smart casual outfits, and many men wear them with suits too.

Dark brown penny loafers worn with olive cuffed trousers — Dark brown penny loafers, image courtesy of @crockettandjones_official // Instagram

Soft Belgian loafers with a small bow, suede driving shoes and leather boat shoes cover warm weekends.

Accessories

Choose silk ties in repp stripes, small geometric patterns or foulards, tied in a four-in-hand knot with a dimple below the knot.

Man in a beige linen jacket and waistcoat, light blue shirt, navy patterned tie and red pocket square — John Wrazej in an Upper East Side style outfit in New York, image courtesy of @johnwrazej // Instagram

A silk or linen pocket square should complement the tie rather than match it exactly.

A simple watch on a leather strap or plain bracelet, plain silver or gold cufflinks or a monogram, and a leather wallet or briefcase without large logos are enough.

Upper East Side outfit ideas by season

Spring

Wear: a light grey suit in tropical wool, a sky-blue cotton shirt, a pale yellow silk tie, brown suede loafers with a brown belt and a beige trench coat for showers.

Summer

Wear: a navy hopsack blazer, a soft pink cotton shirt with an open collar, white linen or cotton trousers and brown leather penny loafers, with a light silk or linen pocket square.

Autumn

Wear: a charcoal flannel suit, a light blue Oxford button-down shirt, a burgundy knitted tie, dark brown cap-toe Oxfords with a matching belt and a camel overcoat.

Winter

Wear: a navy chalk-stripe suit in heavy wool, a white shirt with double cuffs, a green ancient madder silk tie, black Oxford shoes with a black belt, a charcoal wool overcoat and a grey wool or cashmere scarf.

Upper East Side styling guidance

The look rests on a few principles rather than strict rules.

Principle	What it means in practice
Fit	Jackets that close cleanly, sleeves that show a little shirt cuff, trousers hemmed to the shoe
Natural cloth	Wool, cotton, linen and silk for most garments
Few logos	Small or no visible branding
Classic shapes	Two-button jackets, straight trousers, plain overcoats
Small details	A pocket square, a good tie knot, polished shoes

Do

Keep to a calm palette of navy, grey, charcoal, brown and earth tones for suits and jackets.

Have trousers hemmed so they just touch the shoe.

Use collar stays to keep shirt collars crisp.

Choose classic patterns such as fine stripes, small checks and herringbone.

Put cedar shoe trees in leather shoes and rest each pair for a day between wears.

Tie your own bow tie for black-tie evenings.

Keep fragrance light.

Don’t

Rely on large logos or branding to make an outfit.

Leave the bottom button of a suit jacket fastened.

Combine so many patterns that none of them stands out.

Wear socks so short that bare leg shows when you sit down with a suit.

Leave shirts and trousers creased; a steamer or iron keeps them sharp.

Buy clothes for price or label alone.

Conclusion

Upper East Side style is classic city tailoring with relaxed preppy weekends: navy and grey suits, blazers, flannel, Oxford shirts and polished shoes.

Start with a navy blazer, grey flannel trousers, two Oxford shirts, a navy suit, a trench coat and brown and black leather shoes, then add colour through ties, pocket squares and chinos.

Style with The VOU

If you would like help applying this style to your own wardrobe, take our three quizzes, then book a consultation if you want personal help.

Check your body shape with the body shape quiz for men.

Find your seasonal colours with the seasonal colour quiz for men.

Take the fashion style quiz to see which styles suit your taste.

None of the quizzes is needed to wear the outfits in this guide.

For personal help, The VOU offers paid consultations with its stylists, for example a fashion style analysis for men.

Our styling services for men are paid consultations; the shop page lists what each one includes.

Our guide to building a capsule wardrobe explains how to plan suits, shirts, trousers and shoes that combine in several ways.

Upper East Side Style for Men, Classic New York Tailoring and Outfits by Season