Forever 21 Frayed Chevron-Patterned Skirt
Reminiscent of a sophisticated tweed blazer, this A-line midi gives your cool-weather wardrobe an effortless, of-the-moment update. Pair it with a fitted black tee or a steely gray knit.
To buy: $28, forever21.com.
H&M Off-the-Shoulder Blouse White
The basic white blouse gets an update with this retro silhouette, which provides the perfect segue between seasons. Try it with 70s-inspired flared denim jeans.
To buy: $40, hm.com.
BP Tassel Trim Colorblock Poncho Black/White
Draped over a chunky knit and jeans or with a tee and leggings, this knit poncho adds flair to anything it’s matched with. Wear it throughout the fall and winter.
To buy: Unfortunately, this item is no longer available. A similar product can be found here.
Joe Fresh Wide Leg Pants
Looking for a more polished adaptation of the retro flare? Try this silky trouser style, which slims out the hips and thighs and is still dressy enough for the office or an evening out.
To buy: $49, joefresh.com.
Zara Leather Clutch with Fringes
Combining two of the season’s biggest trends—marsala and fringe—this suede clutch makes a simple outfit look more current in one swift maneuver, while also tying together any assortment of neutral or jewel tones.
To buy: $50, zara.com
Mango Strap Ballerina
Set aside your ballet flats in favor of this strappy pointed-toe option. The laces add interest to a standard outfit, like jeans and a tee.
To buy: $50, mango.com.
Aritzia Durandal Sweater Heather Soot
This tunic-style chunky knit balances the proportion of cropped pants and is one of the most wearable trends for fall. Surprisingly flattering with slim pencil pants, it works just as well with flats as it does with heels.
To buy: $125, aritzia.com