October 20, 20265 min read

90s Dad Style Over 40: I Tried 8 Old Money Ralph Lauren Looks

I'm a 40-year-old dad. I tried eight 90s dad, old money looks: Ralph Lauren oxfords, pleated trousers, cords and loose jeans. Here are the five that work.

"90s dads dressed better" is all over my Instagram feed. Oxford shirts, pleated trousers, loose jeans, a leather tote: the relaxed side of old money style, and most of it is Ralph Lauren. I like it on other people, so I tried eight looks to see if it works on a 40-year-old dad. I'm Geir, and I build Thraed. Every photo here is AI-generated with Thraed's virtual try-on and a selfie, so none of them show me wearing the clothes. The verdicts are my honest reaction.

The looks come from @michaeltjacob's 90s Ralph Lauren dad series. Go watch it. He does it better than anyone.

TL;DR: five of eight work. Best: the blue oxford with olive chinos, the taupe knit, and the green sweater with brown cords. Skip the yellow shirt with a tie.

What makes 90s dad style work

A soft, structured shirt or knit, sleeves rolled to the forearm.
Room in the legs: pleated chinos, corduroy or loose straight jeans.
A plain shoe and one real bag: loafers or suede, and a leather tote.

At 40 the trick is fit. The pieces are loose on purpose, but they still hang from your shoulders and waist. That is the difference between "90s dad" and "borrowed your dad's clothes".

Is 90s dad style the same as old money style?

Almost. Both are built from the same clothes: oxford shirts, crew-neck knits, chinos, loafers, and Ralph Lauren under all of it. Old money is the polished version: pressed, tucked in, navy and cream. 90s dad is the worn-in version: looser jeans, rolled sleeves, a tote on the shoulder. If you search for old money outfits for men and they look too stiff for a Tuesday, the looks below are the easy version.

Buy it loose: do not buy slim fit

The one mistake that ruins this look is slim fit. Buy regular, classic, relaxed or straight. The cut matters more than the brand.

Jeans: straight, regular through the thigh. These are the Levi's 501 cut. Skip slim, skinny and tapered.
Shirts: these are Ralph Lauren oxfords with the small pony. Its Classic Fit is the roomiest cut, and Custom Fit is narrower. If a shirt only comes slim, size up one and check the shoulders and sleeves.
Trousers: pleated, relaxed fit. A bigger leg opening in the size table means looser.
Size: your normal size, or one up. Never one down.

Pleated trousers outfit: charcoal shirt, cream trousers, leather tote

Verdict: works. The dark shirt against cream trousers is a strong contrast, and the pleats give the trousers weight. Pieces: washed charcoal shirt, wide cream pleated trousers, brown suede shoes, tan tote.

How to wear a Ralph Lauren oxford: blue oxford, olive chinos, loafers

40-year-old man in a pale blue oxford shirt, olive wide chinos, black loafers and a tan tote on a front step (AI-generated)

Verdict: works, the easiest of the eight. A pale blue oxford is the most forgiving shirt there is, and olive chinos make it look like a decision. Pieces: striped Ralph Lauren-style oxford, wide olive chinos, black loafers, tan tote.

Dress shirt with a tie and jeans: white oxford, loosened tie

Verdict: borderline. The "dad home from the office" look, on the edge of too much. It works with the tie loose and the sleeves rolled. A knit tie and a small knot suit the narrow oxford collar better than silk. Pieces: white oxford, dark tie, light-wash 501-cut jeans, brown suede loafers.

Yellow oxford, navy tie and jeans

Verdict: does not work on me. Yellow plus a tie plus jeans is three loud ideas at once. Without the tie it would be much better. Pieces: pale yellow oxford, navy patterned tie, light-wash 501-cut jeans, black loafers.

Taupe sweater, dark jeans and boots

40-year-old man in a taupe crew-neck sweater, dark loose jeans, brown boots and a tan leather tote in a café (AI-generated)

Verdict: works, the one I would wear on Monday. A plain taupe knit with dark loose jeans needs nothing else. Pieces: taupe crew-neck sweater, dark 501-cut jeans, brown boots, tan tote.

Brown corduroy pants outfit: green sweater and a leather tote

40-year-old man in a dark green crew-neck sweater, loose brown corduroy trousers, brown suede shoes and a tan leather tote outside a bakery in autumn (AI-generated)

Verdict: works, the best fall look. Green and brown are old friends, and the corduroy makes the loose cut look deliberate. Pieces: dark green crew-neck sweater, loose brown corduroy trousers, brown suede shoes, tan tote.

Tan suede jacket outfit: dark sweater and Levi's 501s

40-year-old man in a tan suede work jacket worn open over a dark brown sweater, blue straight-leg jeans and dark brown leather shoes in a living room (AI-generated)

Verdict: works. The most 90s of the lot: short boxy jacket, straight jeans, calm dark sweater. Wear the jacket open. Pieces: tan suede work jacket, dark brown sweater, Levi's 501 cut jeans, dark leather shoes.

Black sweatshirt, Levi's 501s and loafers

40-year-old man in a black crew-neck sweatshirt, blue straight-leg jeans and brown leather loafers on a porch (AI-generated)

Verdict: borderline. The easiest outfit to wear and the least interesting. It reads as "errands on Saturday". Swap the sweatshirt for a knit. Pieces: black crew-neck sweatshirt, Levi's 501 cut jeans, brown loafers.

The score

Five work, two are borderline, one does not. The more colour and accessories I stacked, the worse it got. Calm colours, a good shirt or sweater and room in the legs carried the whole thing. The oxford itself is no fad: Ralph Lauren's own history traces it to a 19th-century Scottish mill and English polo players who pinned their collars down.

Try a look on yourself before you buy it

That is why I built Thraed. Scan the clothes you own, or add a piece you are thinking of buying, and see the outfit on you before you spend anything. Download Thraed free on the App Store and try the look you liked best.