20+ 1920s Fashion Male: 100 Years of Style

I’ve been scrolling through Pinterest and stumbled upon some dapper 1920s male fashion inspiration. Let’s take a trip back to the roaring twenties with these stylish vintage looks!

1920s Fashion Male

Vintage-inspired 1920s Look with a Modern Twist

1920s fashion male 1920s fashion male
by Pinterest

This 1920s-inspired look features a flat cap, a simple white t-shirt, and dark trousers held up by suspenders, exuding a rugged yet classic charm. The ensemble is completed with loafers and a cigar, perfect for channeling a vintage vibe with a modern twist.

1920s Inspired Casual Male Fashion

1920s fashion male male workwear look
by Pinterest

This modern take on 1920s male fashion features a casual yet stylish ensemble with a flat cap, a simple t-shirt, and brown trousers. The look is completed with rugged leather boots and a red neckerchief, adding a touch of vintage flair.

Timeless 1920s-inspired Male Fashion

1920s fashion male simple vintage outfit
by Pinterest

This 1920s-inspired male fashion look features high-waisted, pleated trousers paired with a simple white t-shirt for a casual yet sophisticated style. The outfit is completed with a flat cap and leather sandals, giving it a timeless and effortlessly cool vibe.

Modern Twist on 1920s Fashion

1920s fashion male plain simple outfit
by Pinterest

The essence of 1920s male fashion with a modern twist. The man wears high-waisted trousers paired with a classic white tank top and a newsboy cap, embodying a casual yet stylish look from the era. This outfit is perfect for those looking to channel vintage vibes with a contemporary edge.

Timeless Dapper Style for Men

1920s fashion male classy male outfit
by Pinterest

This 1920s-inspired outfit for men features a classic flat cap, a crisp white shirt, and high-waisted trousers held up by suspenders. The look is completed with brown leather boots, showcasing a blend of vintage charm and modern flair. Perfect for those wanting to channel a timeless, dapper style.

1920s Male Fashion Ensemble Inspiration

1920s fashion male cool aesthetic male retro outfit
by Pinterest

An ensemble featuring high-waisted trousers paired with suspenders, a crisp white shirt, and a flat cap. The look is completed with brown leather boots and a vintage-style bag, perfect for adding a touch of timeless elegance to your wardrobe.

Timeless 1920s Inspired Dapper Ensemble

1920s fashion male peaky blinders style
by Pinterest

A classic flat cap paired with round glasses, a crisp white dress shirt, and high-waisted trousers. The ensemble exudes vintage sophistication and is perfect for those looking to channel a timeless, dapper style.

Vintage Menswear Look with Suspenders

1920s fashion male male outfit inspo
by Pinterest

A striped button-down shirt paired with classic suspenders and a flat cap, capturing the essence of vintage menswear. The look is completed with high-waisted trousers, giving you an authentic, timeless style.

Modern Twist on 1920s Style

1920s fashion male whtie shirt male outfit
by Pinterest

A flat cap, a light button-down shirt, and a neck scarf, giving off a classic yet rugged vibe. The addition of modern accessories like sunglasses and a leather satchel adds a contemporary twist.

1920s Male Fashion Revisited

1920s fashion male oldschool style male
by Pinterest

This photo showcases classic 1920s male fashion, featuring high-waisted trousers held up by suspenders, paired with crisp dress shirts and patterned ties. The stylish fedoras and polished shoes complete the sophisticated and timeless look.

Vintage Sophistication: 1920s-Inspired Ensemble

1920s fashion male timeless male fashion
by Pinterest

A classic flat cap paired with a crisp white shirt and brown suspenders. The high-waisted, gray tweed trousers complete the vintage ensemble, making it perfect for adding a touch of timeless sophistication to your wardrobe.

Vintage 1920s Male Fashion Inspiration

1920s fashion male peaky style male
by Pinterest

Classic 1920s male fashion, featuring a tweed three-piece suit paired with a flat cap and leather boots. The look is completed with a crisp white shirt and a tie, embodying the vintage elegance and sophistication of the era.

Vintage Sophistication: 1920s-inspired Tweed Ensemble

1920s fashion male 1920s suit style male
by Pinterest

This 1920s-inspired look features a classic three-piece tweed suit paired with a henley shirt, flat cap, and leather boots, epitomizing vintage sophistication. Notice the gold pocket watch chain, adding a touch of elegance and authenticity to the ensemble.

Timeless 1920s Dapper Fashion Inspiration

1920s fashion male simple retro male outfit
by Pinterest

The gentleman is wearing a crisp white dress shirt paired with dark trousers and suspenders, capturing the essence of the era’s sophisticated style. The slicked-back hair completes the vintage aesthetic, making it perfect inspiration for a timeless, dapper look.

1920s Male Fashion Revived

1920s fashion male male silhouettes style
by Pinterest

High-waisted, wide-legged trousers paired with a simple white t-shirt. The look is completed with polished leather shoes and a belt, embodying the casual yet sophisticated style of the era.

Vintage 1920s Male Fashion Inspiration

1920s fashion male peaky blinders 1920 style
by Pinterest

High-waisted trousers held up by suspenders, paired with a simple white henley shirt and a classic flat cap. The muted, earthy tones and rustic backdrop enhance the vintage aesthetic, making it a perfect inspiration for those looking to channel a timeless, rugged style.

Timeless 1920s Style Revived

1920s fashion male peaky style retro
by Pinterest

A three-piece pinstripe suit, complete with a pocket watch chain, white dress shirt, and a red tie. The vintage car in the background enhances the timeless elegance of the ensemble, perfect for those looking to channel the sophisticated style of the Roaring Twenties.

Timeless 1920s Male Fashion Guide

1920s fashion male timeless peaky blinders fashion
by Pinterest

A refined look with a pinstripe suit, a crisp white shirt, and a tie, topped with a long overcoat and a flat cap. The addition of leather gloves and a pocket watch chain adds a touch of sophistication and attention to detail. Embrace this classic style for a timeless and polished appearance.

Elegant 1920s Male Fashion Inspiration

1920s fashion male bonnie and clyde style
by Pinterest

A sleek, side-parted hairstyle and a prominent handlebar mustache. The gentleman’s sophisticated look is completed with a tailored suit and a statement ring, embodying the elegance of the era.

Vintage-Inspired Menswear with Modern Twist

1920s fashion male modern peaky blinders look
by Pinterest

A modern twist on classic menswear with a flat cap, layered jacket, and crisp white shirt. The look is completed with tailored trousers and white sneakers, blending vintage charm with contemporary style. Perfect for those who appreciate timeless fashion with a modern edge.

Vintage 1920s Male Fashion Inspiration

1920s fashion male retro timeless male style
by Pinterest

A casual yet sophisticated look. The man is dressed in high-waisted trousers with suspenders, a rolled-up shirt, and a flat cap, epitomizing the classic working-class style of the era. You can draw inspiration from this timeless look to add a vintage touch to your wardrobe.

FAQ

How to dress like a 1920s man?

To dress like a 1920s man, wear a three-piece suit with a matching vest, dress shirt, and trousers, often in tweed or pinstripes. Accessorize with a tie or bow tie, a pocket watch, oxford shoes, and a fedora or newsboy cap for a classic 1920s look.

What did lower class men wear in 1920?

In the 1920s, lower-class men typically wore practical and durable clothing such as work shirts, wool trousers, suspenders, and flat caps. Footwear was usually sturdy boots or shoes, and they often layered with sweaters or simple jackets to stay warm.

Did men wear jeans in the 20s?

No, men generally did not wear jeans in the 1920s. Denim jeans were primarily workwear for laborers, such as miners and cowboys, and were not commonly worn as everyday clothing by most men. Casual and everyday wear typically included trousers made of wool or other fabrics.

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Maximilian Blum
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