Men's Wardrobe Classics That Never Date: Menswear’s Most Enduring Icons

Author: Ryan Blake | Curated for Timeless Style by Tellar.co.uk

Trends shift. Logos fade. But some pieces remain as relevant today as they were fifty years ago. The truly classic menswear item doesn’t rely on hype, graphics or gimmick — it’s all about fit, material, and function. From the crisp white shirt to the navy blazer, these are the pieces that anchor great wardrobes and quietly command respect.

At Tellar.co.uk, we believe timeless style starts with proper fit. We match your exact body measurements to sizing across 1,500+ brands, ensuring your wardrobe classics feel as good as they look. Here's our definitive guide to the menswear icons every man should own — and wear well.

1. The Navy Blazer

Versatile, powerful, and eternally elegant. Whether worn over a T-shirt or a tie, a navy blazer brings structure to any look. Choose unstructured wool for smart-casual use or a structured peak-lapel version for formalwear.

• Drake’s – For softly tailored, easy layering

• Reiss – Clean, modern structure for daily wear

• Paul Smith – A classic with personality, often with a twist lining

2. The White Oxford Shirt

A pillar of classic menswear, the white Oxford shirt works under suits or solo with denim. The thicker weave adds structure, while the button-down collar gives a nod to Ivy League heritage.

• Eton Shirts – Signature twill for pristine finish

• Uniqlo – Budget-friendly, quality weave

• GANT – A modern prep essential

3. Dark Denim

Clean, raw or rinsed indigo jeans are a must. Slim straight fits work across generations. Avoid distressing for maximum longevity.

• Levi’s 501 or 511 – The benchmark in classic denim

• Closed – European denim with minimalist edge

• Jeanerica – Clean, sustainable, well-cut

4. A Camel or Navy Overcoat

Refined, neutral, and strong — a quality overcoat adds polish to even the simplest outfit. Wool-cashmere blends or brushed cotton in camel, navy, or charcoal work for years to come.

• Ralph Lauren – Classic Polo cuts with rich fabrics

• COS – Minimalist silhouettes with modern lines

• Marks & Spencer – Budget-friendly and heritage-inspired

5. The Grey Wool Trouser

Smart, versatile and an unsung wardrobe hero. Pairs with shirts, knits, polos or tailoring. Mid- to high-rise cuts are more flattering and timeless than ultra low-rise versions.

• Drake’s – Flannel and twill tailored trousers

• Reiss – Sleek, modern shapes

• Next – Solid everyday options with generous sizing

6. White Trainers

Crisp leather sneakers are a foundation of modern classic menswear. Clean lines. No big logos. Easy to dress up or down. Leather options age well and add texture to any look.

• Common Projects – The minimalist standard

• Axel Arigato – Sharp lines and premium leather

• Mr Porter Essentials – Sleek white options from legacy labels

7. Chelsea or Derby Boots

Refined boots carry you through winter, smart casual events, and formalwear with edge. Choose polished leather or suede in black, brown or oxblood.

• Cheaney – Handcrafted in Northampton

• Crockett & Jones – World-class construction and shape

• Russell & Bromley – Sleek shapes and reliable quality

Tellar.co.uk: Fit for the Classics

Classics only work when the fit is flawless. At Tellar.co.uk, we help you find the right size and shape across all the brands above. Whether it’s a blazer shoulder or a shirt collar, we match your real dimensions to over 1,500 brands in real time.

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Find your size in 1,500+ brands in real-time. It’s free & easy.Visit Tellar.co.uk