Southern Preppy Style Guide for Men: Clothes, Fabrics and Outfits

Southern Preppy vs. Ivy League vs. Northern Preppy

Southern preppy shares its foundations with the Ivy League look and with Northern preppy, and the differences are mainly about climate and colour.

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Each column describes a common tendency, and many people mix all three.

Our comparison of Northern and Southern preppy explains the regional differences garment by garment.

What history supports

The look grew from the wider American preppy wardrobe, which took shape around north-eastern universities and preparatory schools in the first half of the twentieth century.

No single date marks the birth of a separate Southern version, so this guide sticks to a few documented points rather than a decade-by-decade timeline.

Seersucker, a puckered cotton that originated on the Indian subcontinent, was already sold as summer suiting in the South in the nineteenth century, and the Historic New Orleans Collection has traced advertisements for seersucker suits in New Orleans to 1867.

The New Orleans clothing maker Haspel later did much to promote seersucker suits in the twentieth century.

Madras, a cotton check cloth named after the Indian city now called Chennai, became a summer favourite across American preppy dressing after 1958, when an importer sold Brooks Brothers madras whose dyes ran in the wash and a magazine feature turned the bleeding colours into a selling point, as Ivy Style recounts.

In 1980 The Official Preppy Handbook, edited by Lisa Birnbach, brought preppy clothing to a mass audience across the United States.

In 1996 Senator Trent Lott of Mississippi began Seersucker Thursday in the US Senate, and after a pause from 2012 the custom was revived in 2014, when Bill Cassidy of Louisiana, then a congressman, brought it back in the House and the Senate followed.

Today the look is sold nationally by brands based in the South and elsewhere, which our list of brands below reflects.

Southern Preppy Wardrobe Essentials

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Seersucker Suits

The best-known Southern preppy garment is the seersucker suit, made from lightweight, puckered cotton.

Blue and white stripes are the classic colourway, and the puckered surface holds the cloth slightly away from the skin, which helps air move in heat.

A seersucker suit suits daytime summer events such as a garden wedding or a race day, while a formal evening event usually calls for something darker.

Oxford Shirts

Oxford cloth button-down shirts in white, pale pink or mint green are a versatile base for most outfits.

Wear them with the sleeves rolled and chinos, or under a blazer with a tie.

Khakis

Khaki trousers in medium-weight cotton twill are a year-round staple.

For more colour, try faded red trousers such as Nantucket Reds, which come from Murray’s Toggery Shop on Nantucket rather than from the South but are widely worn there, or pale yellow and light blue chinos.

Madras Jackets

A madras jacket in a light cotton check suits summer parties and outdoor events.

Wear it with a plain shirt and plain trousers so the pattern stands out on its own.

Penny Loafers

Penny loafers in polished leather or suede go with suits and casual clothes alike.

Tassel loafers in burgundy or brown are a slightly dressier alternative.

Boat Shoes

Boat shoes, designed with grippy soles for wet decks, are a casual staple in brown leather.

Brightly coloured versions in red, green, blue or yellow suit beach weekends and relaxed events.

Spectator Shoes

Spectator shoes are two-tone, usually white with brown or black, and add a vintage feel to summer outfits.

They suit daytime spring and summer events rather than everyday wear.

Duck Boots

Duck boots have rubber lowers and leather uppers, and keep feet dry in rain while staying in keeping with the rest of the wardrobe.

Bow Ties

The bow tie is the accessory most closely linked with Southern preppy style.

Repp stripes, madras and plain or patterned silk all work, and a self-tie bow tie looks less uniform than a pre-tied one.

Needlepoint Belts

Needlepoint belts are stitched on canvas with small motifs such as sailboats, golf clubs or animals, and add a playful touch to plain outfits.

Signet Rings

A signet ring is a flat-faced ring that can be engraved with initials, a monogram or a family crest.

In British tradition it is often worn on the little finger, but you can wear it on whichever finger is comfortable, and many people wear one without any family crest.

Pocket Squares

A pocket square finishes a jacket or blazer.

White linen goes with almost everything, and a patterned or brightly coloured silk square adds colour that picks up a shade in your shirt or tie.

Southern Preppy Aesthetic at a Glance

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Southern Preppy Local Variations

The look varies with the setting rather than following fixed state lines.

On the coast, around cities such as Charleston and Savannah, nautical clothes such as boat shoes and striped tops fit naturally with sailing and beach life.

In cooler hill and mountain areas, earthier colours and outdoor clothing such as waxed cotton jackets are more practical for much of the year.

For formal summer events, seersucker suits and bow ties are the most traditional choices.

Main Southern Preppy Fabrics

The fabrics that define Southern preppy are chosen as much for comfort in heat as for appearance.

Southern Preppy Colours and Patterns

The Southern palette is brighter than the Northern one.

Pastel shades such as mint green, pale pink and light yellow are common, usually set against white.

Faded red trousers and shorts add a stronger colour, and navy blue grounds the brighter shades in blazers and accessories.

Blue and white gingham checks are a warm-weather favourite for shirts.

Plaids, from small glen checks to bold tartans, add interest to jackets and trousers, and stripes appear on everything from seersucker suits to repp ties.

If you are new to colour, start with one pastel shirt or one pair of bright trousers and keep everything else navy, white or stone.

Southern Preppy Signature Details

Personal details are a familiar feature of the style.

Monograms on shirt cuffs or leather goods are common; keep them small and in a colour that sits quietly against the fabric.

University and club ties are worn by people with a connection to those institutions, so if you have no connection, choose an unaffiliated stripe or pattern instead.

Small choices, such as how you tie a bow tie or fold a pocket square, make an outfit look considered without needing anything expensive.

Southern Preppy Outfit Ideas by Season

For five more summer looks, see our Southern preppy summer outfit ideas.

Southern Preppy Iconic Figures

A few well-known people are often linked with Southern dressing, for documented reasons.

Southern Preppy Brands to Know

These brands sell clothing in this style; they are examples rather than requirements, and similar garments from any maker work just as well.

Southern Preppy Essential Terms

These words come up often when people talk about the look.

Seersucker: a lightweight, puckered cotton, usually striped, used for summer suits and shirts.

Go-to-hell trousers: brightly coloured or boldly patterned trousers, often embroidered with small motifs.

Madras: a lightweight cotton check cloth named after the Indian city now called Chennai.

Nantucket Reds: faded red cotton trousers and shorts sold by Murray’s Toggery Shop on Nantucket.

Oxford cloth: a basket-weave cotton commonly used for button-down shirts.

Repp tie: a tie with diagonal stripes.

Spectator shoes: two-tone shoes, usually white with black or brown.

Croakies: a brand name for straps that keep sunglasses from falling off.

Sprezzatura: an Italian word from Baldassare Castiglione’s sixteenth-century Book of the Courtier, now used in menswear for studied nonchalance.

Duck Head: a khaki brand that, according to the company, was founded in Nashville, Tennessee, in 1865 and adopted its mallard logo in 1906.

Needlepoint belt: a belt with a design stitched onto canvas.

Monogram: initials embroidered on clothing or accessories.

Documented Southern Preppy Facts

A few well-recorded stories behind the clothes:

1. Seersucker in New Orleans: seersucker suits were advertised in New Orleans newspapers by 1867, decades before the city’s best-known seersucker maker, Haspel, began promoting them.

2. Bleeding madras: in 1958 madras sold to Brooks Brothers ran in the wash, and a magazine feature turned the fading colours into a selling point with the line “guaranteed to bleed”.

3. Seersucker Thursday: the Senate custom begun in 1996 lapsed in 2012 and returned in 2014.

4. Duck Head: according to the company, the Nashville brand added “Head” and its mallard logo in 1906 after its first trademark application, for “Duck”, was rejected.

5. Nantucket Reds: the faded red trousers come from a Massachusetts island shop, Murray’s Toggery, yet are a familiar sight at Southern summer events.

Southern Preppy Style Do’s and Don’ts

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Fit and the silhouette you prefer are different choices, so a relaxed cut and a trimmer cut can both look right if the garment suits your frame.

Conclusion

Southern preppy takes the traditional American preppy fashion wardrobe and adapts it for heat, with seersucker, linen and madras, lighter colours and playful accessories.

It shares much with the Old Money style label and with traditional British tailoring, and some of its accessories, such as signet rings, echo British aristocratic dress, but none of these clothes are evidence of anyone’s background.

Start with the clothes you already own, add one Southern garment such as a seersucker jacket or a pastel Oxford shirt, and build from there.

Quizzes and personal help from The VOU

None of these tools is needed to wear the outfits above, but some readers like extra help when choosing clothes.

You can read about choosing an image consultant and what an image consultant does, and our guides to dressing for your body shape and seasonal colour analysis explain two optional frameworks for thinking about proportion and colour.

For more on dressing for the setting, see styling by occasion, location, season and time of day.

For the vocabulary behind this guide, see our explainers on clothing, garments, fashion accessories, menswear silhouettes and outfits.

We also cover heritage luxury brands and how logo-heavy luxury designs come across, and our fashion style guide explains personal and historic styles.