90s Outfits for Men: 14 Celebrity Looks and How to Wear Them Today

The photograph shows a charcoal zip-front jacket with chest pockets, worn open over a white shirt with the collar unbuttoned, dark pinstripe trousers, black leather shoes and small round tinted sunglasses.

A zipped jacket in place of a blazer keeps the tailored trousers but makes the outfit more casual.

Wear: a charcoal or black zip-front overshirt or shirt-jacket, a white cotton shirt with the top two buttons open, straight charcoal or pinstripe trousers, and black leather Derby shoes or loafers.

Choose a jacket that ends around the hip and has enough room to wear open; a wool or heavy cotton twill version works in cooler weather.

Reiss, COS and Suitsupply are examples of shops that sell overshirts and tailored trousers.

This image pairs two studio photographs rather than showing one suit.

On the left: a white short-sleeved shirt, white pleated trousers with a fine stripe, a brown woven leather belt and white suede lace-up shoes, with a cream jumper slung over one shoulder.

On the right: a cream suit in a slubbed, linen-like cloth, a matching buttoned shirt, a dark pocket square with white spots, white socks and white lace-up shoes with red soles.

Both outfits keep to one pale colour and add a single contrasting accessory.

Wear: a cream or off-white linen or cotton suit with a relaxed cut, a white or ecru shirt, a navy spotted pocket square and white or sand suede Derby shoes.

For a less formal version, swap the suit for a white short-sleeved shirt, pleated cream trousers and a woven belt.

A pale suit works best for warm daytime events, such as a summer wedding where the invitation allows it.

Brunello Cucinelli and Ralph Lauren make linen and cotton tailoring at the higher end of the market, and high-street shops such as Zara sell lighter-weight versions.

The photograph shows a navy single-breasted blazer over a light blue shirt and a dark patterned tie, a brown belt, mid-blue straight jeans and dark shoes.

If the shirt is chambray or denim, as the colour suggests, it gives a double-denim effect next to the jeans.

Keeping a tie with jeans is the unusual touch: the outfit is smart above the belt and casual below it.

Wear: a navy single-breasted blazer, a light blue chambray or denim shirt, a dark knitted or patterned tie, a brown leather belt, straight jeans a shade darker than the shirt, and brown or black leather boots or Derby shoes.

Choose a blazer with enough room through the chest to button over a shirt and tie without pulling.

Levi’s makes chambray shirts and straight jeans, and J.Crew and Uniqlo are examples of shops that sell navy blazers.

The photograph shows a light grey suit with a fine stripe; the jacket has a band collar instead of lapels and buttons high on the chest, with a white crew-neck T-shirt showing at the neck.

The trousers are full and long, worn with a brown belt and brown leather shoes.

A band-collar jacket, sometimes called a mandarin collar, gives a clean neckline and pairs with a T-shirt or a collarless shirt instead of a tie.

Wear: a band-collar jacket in grey wool or linen with matching relaxed trousers, a white crew-neck T-shirt, a brown leather belt and brown leather loafers or Derby shoes.

Band-collar jackets are less common than lapelled ones, so search for “band collar” or “mandarin collar” when shopping new or second-hand, or ask a tailor about a made-to-measure version.

The photograph shows a loose black single-breasted suit with long trousers, and a cream shirt with long collar points worn open and spread over the jacket lapels, with a small pin on one lapel.

The suit is roomy but still follows the line of the shoulder, which is the difference between a deliberately relaxed cut and one that is simply too big.

Wear: a black or charcoal suit with a relaxed cut, a cream or white shirt with a long-point or camp collar worn open over the lapels, and black leather shoes.

Camp-collar shirts are widely sold, and vintage shops are a good source of the longer collar points shown here.

The photograph shows a chunky, flecked oatmeal shawl-collar jumper over a white T-shirt, dark trousers with a corded or velvety surface, and brown suede boots.

The textures do the work: a heavy knit, a soft-pile trouser and suede boots in neighbouring neutral colours.

Wear: an oatmeal or grey shawl-collar jumper, a white T-shirt underneath, dark corduroy or velvet trousers with a straight leg, and brown suede chukka or desert boots.

Shawl-collar jumpers and corduroy trousers appear in most autumn and winter ranges, new and second-hand.

The photographs show Apple’s co-founder on stage in a black mock-neck top with blue jeans and grey trainers, and in a second view a dark mock-neck top with grey-green jeans and brown suede shoes.

NPR, drawing on Walter Isaacson’s biography, reports that Jobs asked the designer Issey Miyake to make his black turtlenecks and that Miyake made “like a hundred of them” (NPR, August 2022).

The lesson is the repetition: one combination worn so often that it becomes a personal uniform.

Wear: a fine-gauge black mock-neck or turtleneck in merino or cotton, straight mid-blue jeans and grey trainers.

Levi’s 501 is one long-running straight-leg jean, and New Balance makes grey running trainers in a similar spirit; the photographs do not show which model he wore.

The photographs show a red cardigan over a yellow polo shirt, pleated khaki shorts with a brown belt, white sports socks and brown leather loafers.

This is a bright, casual take on preppy dressing: the polo shirt, cardigan, khakis and loafers are staples of the American campus wardrobe, worn here in strong colours and with shorts.

White sports socks with loafers are a period touch; dark socks, or none, give a quieter version.

Wear: a red or navy cotton or lambswool cardigan, a yellow or white piqué polo shirt, khaki chino shorts, a brown leather belt and brown penny loafers.

Ralph Lauren, Lacoste and Brooks Brothers are long-running makers of polo shirts, and our preppy style guide for men explains where the polo, cardigan and loafers fit in that wardrobe.

The photograph shows a black single-breasted blazer worn open over a white crew-neck T-shirt, grey stonewashed straight jeans and black pointed-toe boots.

The blazer is long and loose by current standards, which makes the T-shirt underneath look deliberate rather than underdressed.

Wear: a black or charcoal blazer, a plain white crew-neck T-shirt in a heavier cotton that holds its shape, straight grey or washed-black jeans, and black leather Chelsea or western-style boots.

Keep the T-shirt hem above the bottom of the jacket, tucking it in if your blazer is short.

Sunspel and Uniqlo are examples of T-shirt makers, and Reiss and AllSaints sell black blazers.

The original caption identifies the wearer as Rev Run of Run-DMC and dates the photograph to 2002, just after the decade, so treat it as a later example rather than a 1990s photograph.

The photograph shows a black wide-brimmed hat, a long black and grey check wool overcoat, a black roll-neck, black trousers and white trainers.

The idea to borrow is the mix: a formal hat and overcoat finished with clean white trainers.

Wear: a black or charcoal overcoat in a check or plain wool, a black roll-neck, straight black trousers, white leather trainers and, if you like hats, a black felt hat with a wide brim.

Adidas still makes the Superstar, its rubber shell-toe trainer, and any plain white leather trainer gives the same contrast.

The photograph shows a brown houndstooth sports jacket over a light blue shirt open at the neck, a brown leather belt, loose mid-blue jeans and a navy baseball cap with a green underside to the peak.

This is the weekend version of tailoring: a classic jacket made casual by roomy jeans and a cap.

Wear: a brown or grey check sports jacket, a light blue Oxford or chambray shirt, a brown leather belt, relaxed straight jeans, brown leather boots or white trainers, and a plain baseball cap.

Levi’s 505 and 550 are long-running straight and relaxed jean cuts.

For a western touch instead of the cap, a cowboy hat, such as those sold by the Nashville Hat Store, also suits relaxed jeans and boots.

The photograph shows an off-white jacket with a pointed collar and a concealed front, matching wide trousers with turn-ups, a black T-shirt, a silver chain necklace, a black belt with a large silver buckle, black boots and a pale grey cap.

The original caption describes the jacket as white leather; the photograph alone does not confirm the material.

The strong contrast between the pale suit and the black T-shirt, belt and boots is what makes the outfit work.

Wear: an off-white or stone cotton jacket with a shirt collar, matching or near-matching wide trousers with turn-ups, a black crew-neck T-shirt, a black leather belt, black leather boots and, for a casual setting, a cap.

A cotton drill or canvas jacket is easier to wear and clean than leather, while a faux-leather jacket comes closer to the caption’s description.

The photograph shows a light grey check suit, a cream waistcoat in a different cloth from the suit, and a white scoop-neck top in place of a shirt and tie.

The suit is long and roomy, with full trousers.

Replacing the shirt with a plain top under a waistcoat turns a suit and waistcoat into a casual outfit.

Wear: a grey check suit, a cream or stone waistcoat, a white crew-neck or scoop-neck T-shirt that lies flat under the waistcoat, and black or dark brown leather shoes.

A separate waistcoat gives you more outfits than one cut from the suit cloth, because you can also wear it with jeans or other trousers.

The photograph shows a black suit, a black shirt and a black tie with a black knitted beanie and black shoes.

The original caption places it at the 50th Writers Guild of America Awards, held in 1998, and the partly visible lettering on the backdrop is consistent with an annual Writers Guild event.

Keeping one colour from hat to shoes makes a casual beanie look intentional with a suit.

Wear: a black single-breasted suit, a black shirt, a black knitted tie or no tie, black leather Chelsea boots or Derby shoes and, for a casual evening, a black beanie.

Keep the fabrics matt and close in shade so the blacks do not clash, because a shiny shirt next to a matt suit shows the difference.

A beanie with a suit is a fashion choice, so leave it off for black-tie or formal business events.