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Gentlemen

After you read this article, head over to our shopping guide for tips on where to find things like this!

The Gatsby Man

The magic of The Gatsby Picnic relies heavily on the event being an immersive experience. We understand that not everyone has vintage 1920’s outfit in their closet, but there are many creative ways to mix and match modern and vintage clothing, find reproductions, or dress affordably to attend the event. Below are a number of resources to help you curate the perfect outfit and expanded information on 1920’s and 1930’s style.



Think dapper: Fred Astaire, Cary Grant, Gary Cooper and William Powell. Think classic stores like Cable Car Clothiers or Brooks Brothers. Fortunately menswear hasn't changed that much over the years. Even if you feel the need to buy something for Gatsby Summer Afternoon, you may be able to wear it again.

According to Emily Post in 1922 men should wear suits at most occasions, the exception being when he is in the country. Since the Gatsby Picnic is a "country" event, you may wear a light suit or sports clothes.

Hats

A hat is important both to block the sun and as a fashion piece. Try a dashing straw Panama hat or the dapper boater. In the East, men's straw hats were worn only between Memorial Day and Labor Day, but since California was considered a resort destination, they are appropriate during our summer-like weather in September. (That's our story, and we're sticking to it!)

The fedora is a classic and correct in straw or light colored wool. Please avoid the gambler and cowboy hat, unless you are, in fact, a riverboat gambler or cowboy.

For the more casual gentleman or "sport" - the golf cap.

Glasses

Round frames (horn rims or metal) were worn by men and women with no style differences between the two. While round was the most common shape by far, ovals, and octagons were popular. Rimless glasses did exist but their fragility makes them rare. Older gentlemen might wear a pince-nez that stays on by pinching the nose removing the need for arms.

Shirts

Try a long-sleeved cotton dress shirt in white, stripes, or light colors. Short sleeved dress shirts had not yet been invented at this time.

Into the 20s men were still wearing detachable collars and cuffs. The detachable collar and cuff were developed to help shirts last a bit longer. Collars and cuffs wear faster and get dirty easier than the body of the shirt and washing was often expensive. So detachable items were created and sold separately. So a striped shirt with a matching collar is fine, but a striped shirt with a contrasting white collar is perfect.

When in doubt a classic dress shirt in white or pastels is great! Add any of the following for a dapper look: french cuffs, rounded collar, pinned collar, tab collar. Button down collars are considered casual but work great in our summer afternoon environment.

Ties

Traditional ties were often a little on the wider side and worn short with the tip ending just above the belt. A bow tie is also a terrific look. Click here for diagrams of over a dozen tie knots. Tie pins were a very popular accessory in the 20s.

For a less formal look than a tie or bow tie, think about a cravat or ascot with their looser wrap around the neck, especially if it’s hot out.

Ties that match the era can be found for relatively low prices at vintage stores in the area. Look for silk or linen for the most period accuracy.

Jackets, Suits and Vests

The 20s saw some radical changes to men's clothes. Many of the styles are still relevant today. This also means you have a wide variety from which to choose.

The cut of men's suits and jackets varied throughout from the 20s and 30s. The Sacque suit is traditional and what the average man wore. The Sacque has a unstructured fit, but nothing outrageous - think classic Brooks Brothers.

The Oxford suit has a trim jacket with a nipped in waist and very full pants. The "Oxford bag" become popular in 1925 when Oxford University banned the wearing of knickers and plus fours in the classroom (more on these later). The students loved their sporty knickers so they had extra wide legged pants made that could be worn over them.

For the Gatsby Picnic you are shooting for vintage elegant summer day wear. So a suit in a soft color: slate blue, putty, mustard; or a pattern like a glen plaid or hounds tooth. A navy double-breasted jacket with slacks is dapper as well.

Vests

A vest is also suitable to wear. Suits of the 20s and 30s had vests so a jacket with a vest or just the vest itself is appropriate. It would have to be quite a hot day for men to be seen without either.

You can also wear a sweater vest. If you don't have a jacket, a sleeveless sweater vest makes a nice substitute, and looks quite collegiate.

Sweaters

Along with the sweater vest you might try a classic sweater: crew, v-neck or classic cardigan; in cotton, wool or cashmere (though these can be warm). Sweaters should be a solid color, argyle, or plaid. Shopping-wise stick to very traditional and you should hit it on the nose.

Braces

Sometimes also called suspenders, braces are used to hold up the pants instead of a belt. While a belt is perfectly acceptable, braces are more aligned with period era fashions. Consider buttoned braces if you can. Buttons can be sewn into waistbands that don’t have them. Avoid clips as they can damage finer fabrics.

Braces keep pants at your natural waist in the 20s and above it in the 30s.

Braces should not be all elastic. Too much stretch leads to bouncy pants. Authentic braces are Y-shaped and the elastic is on the vertical stem of the Y only. Fabrics can look a lot like neck tie silk but should coordinate, not match, the tie. Braces can also be made of elaborate woven jacquards depicting various motifs and scenes.

Pants

Pants were cut fuller than they are today. This creates a softer drape and an elegant line. The 20s and 30s usually mean pleated pants and the option of cuffs. Bump up the vintage look and add braces. Look for chinos, simple slacks, seersucker, small checks or plaids, in lighter colors and fabrics. Pants in the 20s are worn at the waist, not the hip, and in the 30s they ride a bit above the waist.

Knickers and plus fours (and sixes-eights) all buckle just below the knee. Knickers look like regular pants that stop with a strap and buckle at the knee. Plus fours are four inches longer than the knee but are buckled at the knee creating fullness. Plus sixes and eights are six and eight inches, respectively, below the knee and are fuller but much less common.

Shoes

Look for bucks, saddle shoes, oxfords, or loafers.

Two-tone combinations were in. Men wore brown shoes for day only; two-toned shoes could appear in summer.

In the early 20s, some men were still wearing spats.

Socks

Socks are part of the whole look. They can be very thin dress socks that match the pants or thicker with cables or patterns to wear with knickers.

Remember to have fun combining patterns and colors. They did at the time. A striped shirt, paisley tie, plain vest, tweedy-plaid knickers, argyle socks and saddle shoes could be, if done well, the height of fashion.

Click here for Emily Post 1922 on Men's Clothes.

In summary…

  • Straw hat: boater or panama

  • Flat cap with brim; a more sporting look

  • Shirts: long sleeved, plain or pale color, simple stripes, french cuffs or plain

  • Ties: straight or bow, foulard, small geometric prints, stripes

  • Can't abide ties? Try an ascot

  • Pants: classic styles, light fabrics (seersucker, linen, chino) in light, neutral colors

  • Use braces (suspenders) or a belt, never both

  • Shoes: Lace-ups, could be two-toned (If you have foot problems, choose a neutral, shoe-like sneaker)

  • Jackets: single or double-breasted

  • Suits with matching pants or sport jackets

  • Vests look smart if you need to remove your jacket in the heat

  • Sweater-vests are a youthful look, more casual than a suit or jacket

  • Final touch: the pocket square, neatly folded and ironed or gracefully fluffed and inserted in the jacket breast pocket

Some Gatsby-ites dress in real sport wear (as opposed to sportswear). As you can see in the image above, even dressing for sport is not an easy way out. Tennis (above far right) means white (or cream): white shoes, white pants, white socks - the works. Men golfed in either tweedy suits or plus-fours with a sweater vest.