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August 27, 2023

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Classic Menswear : A Timeless and Sophisticated Style

Menswear has gone through many changes over the decades, but classic menswear has remained a staple in many men’s wardrobes. This timeless style exudes sophistication and confidence. In this comprehensive guide, we’ll explore everything you need to know about achieving the classic menswear look.

What is Classic Menswear?

Classic menswear refers to a polished and refined style for men that focuses on high-quality fabrics, tailored fits, and timeless silhouettes. This look has its roots in British tailoring and style from the early 20th century.

Some key elements of classic menswear include:

Well-tailored suits in materials like wool and linen
Button-down dress shirts often in white or light blue
Leather dress shoes in black or brown
Ties and bow ties
Blazers and sports jackets
Trousers like chinos and wool pants
Sophisticated overcoats and topcoats
Pocket squares and silk ties
Leather briefcases and satchels

The overall aesthetic is clean, sharp, and polished. It’s meant to convey a distinguished and cultured flair.

The Origins of Classic Men’s Style

Classic menswear as we know it today has its beginnings in the early 1900s style of dress in Great Britain. Wealthy British gentlemen began moving away from the over-the-top Victorian aesthetic and gravitating towards a more refined tailored style.

Savile Row in London became the epicenter of men’s tailoring, establishing the elegant silhouette and impeccable craftsmanship that’s still associated with English bespoke tailoring today. This new pared-down yet sophisticated style spread to men across Europe and America throughout the early decades of the 20th century.

Some key style icons that paved the way for classic menswear include:

The Duke of Windsor: His preference for softer silhouettes and unstructured jackets brought ease and modernity to men’s tailoring in the 1920s/30s.
Cary Grant: The legendary actor exemplified suave tailoring in the 1930s/40s with his preference for bold striped ties and peaked lapels.
Fred Astaire: Known for sporting tailored suits, silk scarves, and leather loafers both on and off screen in the 1930s.
Sean Connery’s James Bond: Brought the classic menswear look into the mainstream with his slim cut suits and bow ties in the 1960s.

These style mavericks took classic tailoring in a more relaxed and modern direction while still retaining the refined elegance of traditional British menswear. This timeless aesthetic still informs the classic men’s style we appreciate today.

The Key Elements of Classic Menswear

Achieving the classic menswear look is all about sticking to timeless pieces that emphasize quality and restraint. Here are some of the essential style components:

Tailored Suits

The foundation of any classic menswear wardrobe is a crisp tailored suit in a neutral shade like navy, grey, or charcoal. Opt for a two- or three-button single-breasted jacket with notched lapels and slightly padded shoulders for structure. Pair it with flat-front trousers that sit at your natural waist. Wool and linen are ideal suit fabrics that keep their structure while remaining comfortable.

For optimal versatility, build your suit collection around these staple pieces:

Solid navy suit
Grey checked three-piece suit
Tan linen suit for summer

Crisp Button-Down Dress Shirts

A well-fitting dress shirt in white, light blue, or subtle stripes is another menswear essential. Choose 100% cotton styles with a semi-spread collar and front button placket. Most classic button-downs will have a box pleat along the back and a locker loop. This versatile piece pairs well with suits but also looks smart on its own.

Leather Dress Shoes

Quality leather dress shoes are a must for finishing off your look. Opt for lace-up Oxford styles in black or brown leather with a sleek cap toe. Go for leather soles and heels for durability. Make sure to properly polish and care for your shoes to maintain their shine. Monk strap, Chelsea boot, and loafers can also work for smart casual outfits.

Ties and Bow Ties

A sharp tie or bow tie brings polish and color to your tailored ensembles. Build a collection around neutral and muted patterns like stripes, dots, checks, and paisleys. Ties made from silk or wool are best for retaining shape and sheen. Bow ties are a fun alternative for black tie and formal events.

Blazers and Sports Coats

A well-fitting blazer or odd sports jacket adds versatility to your tailored wardrobe. Opt for jackets in hopsack, flannel, and tweed to layer over dress shirts and odd trousers. Notched lapels and patch pockets keep the look refined. Navy, olive, and grey make useful blazer colors for both casual and formal looks.

Overcoats and Topcoats

An overcoat or topcoat is essential for staying dapper in cold weather. Look for knee-length wool and cashmere styles in black, grey, or camel. Choose a single- or double-breasted silhouette with wide lapels, welt pockets, and a back vent for ease of movement. This polished top layer protects your suiting from the elements.

Accessories

Don’t overlook the importance of accessories in pulling your look together:

Pocket squares: Add a pop of color and pattern to your suit with a folded pocket square made from silk, linen, or cotton.
Tie bars and clips: Functional and decorative tie accessories provide a refined finish. Opt for simple designs in silver, black, or gold.
Belts and suspenders: Leather belts coordinate with your shoes, while suspenders provide an old-school accent.
Hats: A felt fedora or panama hat shows vintage sophistication.
Scarves: Silk neck scarves add flair in cooler weather.
Sunglasses: Wayfarers, aviators, and clubmasters all offer a dapper accent.
Briefcases and satchels: Carry your necessities in style with a leather or canvas bag.

Smart Casual Pieces

You can break from full suiting with smart separates like odd jackets, knitwear, and casual trousers. This allows you to exude sophistication while remaining comfortable and relaxed.

Key smart casual staples include:

Odd trousers: Chinos, wool trousers, and neat jeans open up options beyond your suit pants.
Knitwear: Crewneck sweaters, cardigans, and knitted polos pair well with trousers and relaxed button-downs.
Sport shirts: Checked flannel and chambray long-sleeve shirts offer a rugged yet refined look.
Desert boots and loafers: These shoes straddle the line between formal and casual.

Mixing these transitional pieces allows you to go from the office to evening engagements with ease while upholding your refined aesthetic.

How to Wear Classic Menswear for Different Occasions

One of the virtues of classic menswear is its versatility across occasions. With a few adjustments, you can easily go from a client meeting to a friend’s wedding while looking appropriately dressed.

Here are some tips for wearing classic style for different events:

Office Attire

Suit: Opt for your navy or charcoal suit, paired with cap toe oxfords, a white dress shirt, and complementary tie.
Separates: Swap the full suit for dress trousers, a blazer, and an open-collar shirt on more casual office days.
Accessories: Leather briefcase or satchel. Stainless steel watch. Fountain pen.

Cocktail Parties

Suit: Wear an unlined peak lapel tuxedo for black tie optional affairs.
Shirt: Swap your crisp white shirt for a more festive style with French cuffs.
Tie/bow tie: Go for a silk bow tie or velvet neck tie in a jewel tone or metallic sheen.
Shoes: Patent leather or velvet loafers.
Pocket square: Opt for a bold coloured silk.

Weddings

Suit: A tailored three-piece suit is ideal for such a formal event.
Shirt: French cuff shirt in white or pale blue.
Tie: Complement your date’s outfit with a silk neck tie.
Shoes: Cap toe oxford dress shoes.
Accessories: Pocket watch and chain. Silk pocket square.

Casual Weekends

Trousers: Swap your suit pants for chinos or neat denim.
Shirt: Button-down dress shirt or polo shirt.
Shoes: Loafers, Chelsea boots, or leather sneakers.
Jacket: Unstructured blazer or cotton sport coat.
Accessories: Leather weekender bag. Wayfarer sunglasses. Baseball cap.

Dressing down your tailored pieces for weekends gives you a sophisticated casual look.

Essential Pieces for Building a Classic Menswear Wardrobe

Curating a versatile classic menswear wardrobe is more about cultivating timeless staples rather than trendy statement pieces. Focus on quality over quantity. Here are some of the must-have items to look

Wardrobe Essential	Details
Navy Suit	Notch lapel, two button jacket with flat front trousers
Grey Suit	Sharkskin or glen plaid three-piece suit
White Dress Shirt	Barrel cuffs, semi-spread collar
Light Blue Dress Shirt	Button-down collar
Black Cap Toe Oxfords	Leather soles, sleek finish
Tan Monk Strap Shoes	Versatile smart casual style
Black Leather Belt	Coordinates with your shoes
Grey Overcoat	Knee-length, wool-cashmere blend
Navy Sport Coat	Two-button, patch pockets
White Linen Pocket Square	For adding polish to suits
Stainless Steel Watch	Slim case and leather strap
Tortoiseshell Wayfarers	Flattering and timeless frame

Slowly build up these wardrobe basics that align with your personal style preferences. Quality over quantity will ensure you get years of use from each piece.

Tailoring Tips for a Polished Fit

Achieving the right fit is crucial to looking sharp in classic menswear. Ill-fitting suiting will look sloppy rather than sophisticated. Follow these tips for a tailored fit:

Take accurate measurements rather than going by generic sizing
Allow enough room for comfortable movement through the shoulders and sleeves
Keep sleeve lengths short enough to reveal just a hint of shirt cuff
Opt for a tapered cut through the torso and legs for a slimming effect
Trouser breaks should hit right at the top of your shoes
Have any final adjustments made by a qualified tailor
Maintain your shape by having pieces retailored over time

Investing in custom tailoring and alterations makes all the difference in looking polished rather than messy. Taking the time to get the right fit will ensure your look makes a refined impression.

How to Care for and Maintain Classic Menswear Staples

Caring for your classic menswear investment pieces will keep them looking their best for years. Follow these tips to protect the quality of your tailored wardrobe:

Suiting and Tailored Jackets

Invest in a clothes steamer to smooth out wrinkles and refresh the shape of jackets.
Use cedar hangers to store suiting and blazers. This helps absorb moisture and retains the shape of the shoulders.
Have your most-worn pieces dry cleaned 2-3 times per year. Spot clean as needed between cleanings.
Wool and linen pieces should be dry cleaned only.

Shirts

Allow cotton dress shirts to air dry to avoid shrinking. Dry clean silk shirts.
Wash shirts on a gentle cycle using mild detergent and cold water.
Iron shirts while still slightly damp using medium heat.
Have delicate collar and cuff edges hand washed if discolored.

Ties and Accessories

Roll up ties rather than hanging them to avoid creases.
Use a fabric shaver to gently remove lint or fuzz.
Spot clean stain-resistant ties with a damp cloth. Dry clean silk and wool varieties.
Leather shoes and belts should be polished and conditioned regularly to prevent drying.

Taking care of the details keeps your look polished.

Finding Classic Menswear Pieces

You can build a timeless classic wardrobe from a mix of the following retail sources:

Department Stores

John Lewis: Wide range from formalwear to smart casual pieces.
House of Fraser: Extensive selection of tailoring and accessories.
Debenhams: Reliable high street option for menswear essentials.
Harvey Nichols: High-end designer offering.

Independent Boutiques

Oi Polloi: Refined British and European menswear.
Grenson: Heritage English shoe styles.
Drake’s: Elegant neckties and accessories.
Club Monaco: Updated classics and tailoring.

Online Retailers

Mr Porter: Global luxury menswear hub.
Matches Fashion: Designer styles with next-day delivery.
End.: Carefully curated menswear edit.
Oi Polloi: Refined British classics.

Mix high street stalwarts with designer brands and boutiques to build a well-rounded wardrobe.

Thrift and Consignment Shops

You can often uncover quality classic menswear pieces for less at:

Charity shops: Check shops in affluent areas.
Vintage markets: Search for unique retro finds.
eBay: Extensive range of new and preowned.
Depop: Treasure hunt for secondhand gems.

With some hunting, pre-owned pieces can make great additions to your wardrobe. Be sure to examine items carefully for damage before purchasing.

Incorporating Modern Updates

While classic menswear adheres to a timeless aesthetic, you can make it feel relevant by blending key elements with current styles. Subtle modern updates like these keep your look feeling fresh rather than dated:

Slimmer silhouettes: Opt for a more tailored slim fit on suits and overcoats than traditional boxy shapes.
Textured fabrics: Incorporate interesting fabrics like wool flannel, organic cotton, and textured outerwear.
Casual influences: Mix your tailoring with laid-back staples like neat knitwear, white sneakers, chinos, and bomber jackets.
Tonal palettes: Monochrome looks in shades like camel, navy, grey, and black feel modern.
Discreet patterns: Small-scale checks, textured stripes, micro dots and subtle plaids update your shirting and ties.
Minimal accessories: Skip over-accessorizing for a cleaner contemporary look. Stick to one statement piece like a watch or hat.

Use these current touches to keep your classic style feeling fresh rather than like a throwback.

How to Wear Classic Menswear at Any Age

From recent graduates to retirees, well-executed classic menswear has appeal across ages. Make sure your look aligns with your lifestyle and stage of life.

Your 20s

Key pieces: Slim chinos, knit polos, unstructured cotton blazer, trim cut suits.
Keep it: Casual and youthful with sneakers and muted colors.
Avoid: Anything too stiff, aged, or overdone.

Your 30s and 40s

Key pieces: Tailored wool suits, dress trousers, leather shoes, trench coat.
Keep it: Polished for the office, relaxed for weekends.
Avoid: Trying too hard to look young or trendy.

Your 50s and Beyond

Key pieces: Lightweight sweaters, smart overcoat, silk pocket squares, felt hats.
Keep it: Distinguished and cultured.
Avoid: Outdated styles that might age you further.

Adjusting the core items and overall vibe allows gentlemen of all ages to incorporate this timeless aesthetic.