Men’s Gatsby Hairstyles Bring the Dapper

It would be inaccurate to say that men’s Gatsby hairstyle has just arisen because there has been around the classic hairstyle for years. Over the years, numerous variations have spawned around its elegant existence in this pomade hairstyle.
Since time immemorial, the fashion is based on the side swept hairstyle synonymous with the wealthy and the elegant. The appeal is still there, making it one of the best options for anyone who wants to bring out the gentleman in him. Here are 25 elegant hairstyle variations.

1 Classic Side Sweep Hairstyle

This hairstyle variant takes on an approach of more than 50s with a flat top and closely swept side skin. This was more popular with the men of yesteryears, but when done on medium to short hair, it can still look dapper. The bold line of division emphasizes the tapered sides.


Modern Gatsby hairstyle versions feature a more prominent top. Due to the sheer length of the top, this particular variation carries a subtle rough edge. Using a straight parting line, the side swipe is emphasized, giving it the classic appeal of dapper synonymous with hairstyle.

3 High Top Classical Side Sweep

Admittedly not everybody’s cup of tea. It has a relatively flat top with some thickness in the direction of the forehead. The classic side sweeping and tapered sides cap off this hairstyle’s gentlemanly appeal.
4 Traditional Side Swept Hairstyle

Who better than DiCaprio to wear a side sweep? This hairstyle version features a state-of – the-art side sweep without distinctive parting. It’s a great look for medium to long hair with the enhanced top volume highlighting the hairstyle sophistication.

5 Gatsby Hairstyle with Tapered Sides

This hairstyle is beautiful because it opens the way for creativity. The sides have a more pronounced taper in this case to emphasize the voluminous edges. Even with medium hair, if you’re looking for a chic side sweep, this classic look will suit you perfectly.

6 Sliced Back Top with Tapered Sides

This variation wanders away from the most common designs and features a long sliced back top with steeply tapered sides that enhance its prominence. For long to medium hair, the classic hairstyle fits well.

7 Thick Top Side Sweep with Razor Fade

A more hip hairstyle version that still makes waves (forgive the pun) in fashion is the voluminous top with a sweeping, though minimal, sidewalk. The hairstyle focal point is intensified by razor-faded ends, resulting in a modern and classic hybrid version of the haircut of the gentleman.

8 Slick Back Top with Low Bald Fade

Modern tape-up hair-cut fade blends with timelessly sleek side sweeping to create an elegant blend between the two. Safe to say, the two models bring out each other’s charm, with the sleek fade placing more attention on the long-haired, slicked back top.

9 High Fade with Wavy Pomade Top

This bold haircut features a crazy mix of modern high tapering bald fade with a wavy top swept aside in trendy style. In this perfect example of how versatile the classic Gatsby is, the subtle beard disconnect adds taste to the classic look.

10 Wavy Side Sweep with Layered Tapering

Unlike modern fades, the sides are tapered layer by layer using scissors from a barber. This look reflects the classic Gatsby riding on one temple from the wavy, side-swept locks on the crown to the strikingly elegant parting line.

11 Slicked Back Gatsby with Tight Top

Men preferred to keep their hair short as seen in this instance in the daytime. This is one of the initial look models that featured heavily cut back short to medium-length hair to create a clear outline and straight hairline.

12 Medium-Haired Slick Back

This look was predominantly associated with past villains. The slightly wavy short hair on the crown was cut back tightly and the sides tapered a little to emphasize the top length. True to the fashion of Gatsby, no forelock remains unmanaged.

13 The Vintage Gatsby

This hairstyle lacks the flamboyance of some imaginative variants of the side sweep, but it makes up for it with an admired class sense. The smooth side swept top is smooth all the way with a slight fade temple giving elegance and uniqueness to the hairstyle.

14 Wavy Side Sweep

This is one of the classic models that gentlemen from all over the world have kept on well. With its elegantly swept side style, the finger-curled top exudes sophistication. The top and medium-length sides are distinguished by a dividing line at the temple.

15 High Top Side Sweep with Temple Fade

Another creatively enhanced version of gentleman’s hairstyle is this crossover featuring a classic side swept top with a bold tapering down the sides ending in a temple fade. Using long, short and medium hair, the look can vary.

16 Classic Slick Back with Tapering Bald Fade

In common style, the thick top was slicked back with pomade. The sides take on a different fashion, the tape up, as they constantly taper and then quickly fade into the temples ‘ skin. The disconnection of the beard is a nice touch but the moustache of the handlebar is a matter of personal preference.

17 Regal Side Sweep

This hairstyle is just as formal as it is Gatsby. The long-haired crown was swept to the side elegantly and divided on the temple. Below it, on the side where the hair lies, the sides were drastically tapered to a razor fade.

18 Gatsby with locks

Without having to give up the locks you can still rock the side swept look. Just a few forelocks dangling over the forehead, this variant breaks out of practice. The curly crown is swept slightly to the side on the other side of the sweep with a touch of parting.

19 Vintage High Top

This iconic side sweep shows traditional swept hair piled up on the top of the forehead with an imaginative forelock. Both sides are tapered down to give the top a larger appearance and also to enhance the head’s symmetrical shape.

20 Bold Side Sweep with Tapering Skin Fade

This look combines beautifully an artistically tapering fade that blends right into the skin with an elegant side-swept top with a distinct parting line running along the length of the crown. For an elegant look, the hairstyle features perfect, distinct lines and boundaries.

21 Sliced Back Top with Tapered Sides

This look features a pretty large top for people who want to keep their hair length. With a gentle temple fade on the tapering sides, it is swept back elegantly only to accentuate its prominence.

22 Side Sweep with Low Skin Fade

If you prefer something with more refined contrasts and boundaries, this hip and sophisticated side sweep combines a sleek gentleman’s look with an edgy low skin fading about two inches from the ear which makes the look bold.

23 The Suave Gatsby

This is a hairstyle that only the most dapper of us can pull off. This features a perfectly slicked top and sides with a bright line running down the temple’s edge to the center of the chest. A slight back and side taper caps off what is one of the Gatsby’s sleekest variations.

24 Sweep Side Sweep with Groomed Beard

While the side sweep is usually accompanied by clean shavings or minimally bearded heads, a full beard looks just as striking with this hairstyle. The side sweep is comprehensive with a line running along the temple’s bottom.

25 Tapered Side Sweep