Dressing for dates during the fall season can be a tricky endeavor, frankly because the weather & temps can be so unpredictable throughout the day. I’m personally someone who likes to mix something cozy with something structured, in a compromised ensemble.

One of the best ways I’ve accomplished this is through the pairing of cozy sweaters with structured mini skirts, and a great bootie to seal the deal. But the trick to stepping this look up is all in the details – from sleeves to fabric to hardware involved in the pieces worn.

BALLOON-SLEEVE SWEATER

This style is probably my favorite to wear because it makes wearing something ‘oversized’ much more appealing to the eye. The sweater is made to fit the torso & generous in the sleeves; this ends up drawing the eye outward away from the waist, giving the appearance of a smaller frame.

Favorite styles in white: One, Two, & Three

…

TWEED MINI SKIRT

One of the best fabric choices to wear in the fall, especially for chillier days. Like florals are to spring, tweed is a seasonal fall/winter staple that will never go out of style. We can probably thank Chanel & their signature tweed suits for the continuation.

Under $25 styles I love: One, Two, & Three

…

STUDDED BOOTIES

Who doesn’t love a bootie with a touch of edge? I find myself drawn to pairs with such hardware because it breaks up the femininity of most skirt & sweater combos. I think of studded black or white booties act like neutrals when it comes to an ensemble & worth the investment, as they can work with almost any color combination of top & bottom.

Similar styles on sale: One, Two, & Three

The biggest takeaway I can reiterate about the above (3) pieces is that they’re evergreen to your wardrobe. No matter what, they will never go out of style during the fall/winter seasons & continue to be versatile for endless outfit rotations.

Tweed Skirt: Forever 21 | Sweater: ASOS (old, similar here & here) | Booties: Rebecca Minkoff (old, similar here) | Bag: Chloe