Photo: Devon Jarvis/Studio D

Am I too old for a leather jacket?
You can never be too old for the right leather jacket. It's timeless, flattering and appropriate for many occasions. But you have to search a little to find a keeper. I've done the legwork and picked out a great jacket for every age—plus some fantastic pieces to go with each.

Chaser, $231; LuLus.com.

Photo: Devon Jarvis/Studio D

Wear it with...
Top, Nic + Zoe, $128; NicandZoe.com. Bag, $98; DeuxLux.com. Skirt, M Missoni, $595; 212-431-6500. Sandals, $498; StuartWeitzman.com.

Photo: Devon Jarvis/Studio D

City Sleek
$450; ArmaniExchange.com.

Photo: Devon Jarvis/Studio D

Wear it with...
Dress, $98; BCBGeneration.com. Scarf, Stella & Dot, $69; StellaDot.com. Earrings, $50; LisaFreede.com. Sneakers, DKNY Active, $150; DKNY.com.

Photo: Devon Jarvis/Studio D

Polished Rocker
Joe Boxer, $30; Kmart.com

Photo: Devon Jarvis/Studio D

Wear it with...
Top, Calvin Klein, $59; Belk.com. Sunglasses, $180; WestwardLeaning.com. Skirt, $23; OldNavy.com. Pumps, Diane von Furstenberg, $325; DVF.com. Watch, $325; CitizenWatch.com.

Photo: Devon Jarvis/Studio D

Modern Elegance
$390; MassimoDutti.com.

Photo: Devon Jarvis/Studio D

Wear it with...
Top, $295; ToryBurch.com. Capri pants, Rafaella, $35; RafaellaSportswear.com. Wedges, Jack Rogers, $178; JackRogersUSA.com. Bag, $395; Brahmin.com.
From the June 2015 issue of O, The Oprah Magazine