Layering skirts or dresses over pants is one of those controversial mid-aughts trends I never thought I would participate in again, only to have one cool girl on Instagram instantly change my mind. Now I understand the genius of this unconventional layering technique: all the fun of a sundress, all the warmth of a trouser. It’s perfect for transitional weather as you reintroduce spring styles into your late-winter rotation. I understand if you’re still skeptical (the bubble skirt I wore over skinny jeans in 5th grade still haunts me too), but if you’re curious, we’ve curated three fool-proof ways to wear skirts and dresses over pants that’ll open up a world of styling possibilities.
Midi Sundress + Denim
Sundresses aren’t just for summer—pair your favorite with straight-leg denim and a warm varsity jacket on a sub-60-degree sunny day.
Twiggy Jacquard Cutout Puff-sleeve Midi Dress
Margo Colour-block Varsity Jacket
Plein Straight-leg Jeans
Tabi 55mm Ankle Boots
Mosaic Bag
Pearl Necklace With Strawberry Embellishment
Sweater + Trousers + Pleated Skirt
This outfit is an excellent example of how to wear a lot of fabric and not feel overwhelmed. The sharpness of the slicked bun, pleats, and boot balance out the oversized sweater and wide-leg trousers. All of these come together in a polished yet cozy look.
Turtle Neck Jumper
Asymmetric Pleated Skirt
Plaid-check Wide-leg Trousers
Pointed-toe Ankle Boots
Acetate Sunglasses
Color Blocked Skirt + Trousers + Coat
Don’t be intimidated by the unique proportions and color combinations in this look—pick a looser-fitting pencil skirt, trouser, and coat in a solid palette that appeals to you, and you can do no wrong.
Funnel-neck Satin Blouse
High-waisted Wide-leg Cargo Trousers
Belted Leather Midi Skirt
Teddy Fabric Jacket
Juanita 70mm Slip-on Pumps
Horsebit 1955 Shoulder Bag
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