Ilaria's Picks

Dress Your Age

Age is just a number… except when it comes to style. And, honestly, you may not want to hear this, but if you’re over 35—this applies to you too. So pull up your pants and read up.

PULL UP YOUR PANTS.

This should go without saying… and yet.

TURN IN YOUR BOY BAND SHOES FOR A MINIMAL SNEAKER.

Unless you’re a pro-skater or in a band, it’s time for a nice minimal sneaker. A white pair is a no-brainer; they work with anything and anywhere.

CONSIDER A CHUKKA BOOT.

Elegant, underrated, and hint of European professor—which is never a bad thing. Great with jeans, chinos, or trousers.

DITCH THE SKINNY JEANS.

Slim, good. Skinny, bad. Tapered, helps. Don’t let the door hit your skinny jeans on the way out. Bye forever.

5-POCKETS ARE GOOD. TROUSERS ARE BETTER.

Get some adult pants. And get to love pleats. Don’t worry, these are not your father’s pleats.

cos crepe chino pants on leo edit

Cos Crepe Chino Pants $125

alex mill pleated pant in wool herringbone on leo edit

Alex Mill Pleated Pant in Wool Herringbone $145

ADD A BELT (SOMETIMES).

A good, not too wide belt with a slim buckle can pull your look together and give you a waist line. But I cannot emphasize this enough: leave the logo-buckle to your teenage daughter.

TURN IN YOUR T-SHIRT FOR A KNIT POLO.

If you’re following along, we’ve covered this.

T-SHIRTS: V-NECK, BAD. CREW-NECK, GOOD.

This applies at any age. Remember the American Apparel hipsters of the early aughts? Did they look like grown-ass men to you? If that doesn’t make the case, have you ever seen a photo of James Dean, Paul Newman, Steve McQueen, Alain Delon, or Marlon Brando—to name a few of the best dressed men of all time—in a V-neck tee? No. (To be clear, this only applies to t-shirts. A V-neck sweater is great.)

GOOD EYEWEAR IS ALWAYS A GOOD IDEA.

A great style fit will instantly be tainted by a bad pair of glasses. On the flipside, a mediocre look is instantly improved by great eyewear.

GET RID OF THAT STUPID SCARF.

Unless you’re Steven Tyler, there should be absolutely no purpose for your scarf other than to warm up your neck when it’s actually cold outside. Good news, though, a great cold-weather scarf is always dashing.

drake's glen check wool scarf on leo edit

Drake’s Glen Check Wool Scarf $68

H&M Jacquard-weave scarf on leo edit

H&M Jacquard-weave Scarf $18

SEND YOUR LEATHER CUFFS, BEADS, AND ANCHORS TO GOODWILL.

Man-jewelry is tricky. When it’s wrong, it’s very wrong. For the most part, rings are great, if you ask me. A simple chain with a good amulet always works—steer clear of cliches like anchors or daggers. The right bracelet can work, but if it looks like you bought it at a Venice beach booth in the 90s, it’s a pass. For whatever reason, pieces with religious connotations rarely fail. And I do love a pinky ring. I guess guido never goes out of style (I’m Italian, I can say that).

STEP UP YOUR SOCK GAME.

Go into your sock drawer and get rid of every pair of socks with: 1) A hole. 2) Any pair that looks like it belongs in 8th Grade P.E. 3) Or that just look, you know, sad. 4) Prints are good. We love prints. Unless it’s something overly cute-sy (tacos), overly waspy (lobsters), or emo (skulls). And invest in a good set of no-shows.

LOSE THE FLIP FLOPS.

For one thing, no one is particularly dying to see your toes. And, I’m sorry to break it to you, but leather sandals are even worse. Less immature, sure. But just worse in every other way. Let us offer some alternatives.

INVEST IN A GOOD WATCH.

A good watch just ties the whole room together. It’s the investment piece you should strive for.

UPGRADE YOUR WORK BAG.

One day, you may return to an actual office. And when that day comes, you’re gonna look damn ready.

LOSE THE BELLS AND WHISTLES.

God or the devil may be in the details, but elegance is in simplicity.

All products featured in LEO are selected on their merits. We may receive a commission through our retail links. Since all links do not earn commission, we appreciate your purchasing through LEO links when possible so that we can keep bringing you great content.

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