An FP Stylist shares her 5 ideal pairings…

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It’s a dilemma that’s likely hounded you for as long as it has me.

WHAT SHOES SHOULD I WEAR?

Donning a sneaker on one foot, a random clog on the other…trying to ascertain which one actually complements the jean inseam, silhouette (or even skirt or dress) I’m wearing? There are so many variables at play at any given time…

But, our in-house stylist, Julie, is here with a few key tips on choosing – and styling – the shoes to pair with five of our favorite “now” bottoms.

What Shoes to Wear with Mini Skirts: Combat Boots

The Bottom:
Levi's Icon Skirt

The Shoe:
Jones Tall Lace Up Boots

Why It Works:
Chunky combat boots balance miniskirts in proportion and style – opposites attract!

Pro Tip:
The toughness of the combat boot adds a touch of edge to any preppy look.

What Shoes to Wear with Barrel Jeans: Moto Boots

The Bottom:
We The Free Lucky You Mid-Rise Barrel Jeans

The Shoe:
We The Free Briggs Crop Rider Boots

Why It Works:
Wide shaft moto boots that hit just above the ankle offset the volume of a barrel-shaped bottom.

Pro Tip:
Roll the cuff and show off that hardware for extra personality.

What Shoes to Wear with Cropped Jeans: Ankle Boots

The Bottom:
We The Free In My Feelings Cropped Slim Flare Jeans

The Shoe:
We The Free Briggs Crop Rider Boots

Why It Works:
Cropped flare jeans frame ankle boots with the perfect length/width to show those boots off.

Pro Tip:
Added hardware and a moto jacket keep things cool.

What Shoes to Wear with Barrel Shorts: Knee-High Boots

The Bottom:
We The Free Extreme Measures Barrel Shorts

The Shoe:
Friday Fever Heel Boots

Why It Works:
Knee-high boots paired with long-line shorts give the right amount of coverage for fall. The sleekness of this stiletto boot counters the oversized short and jacket beautifully.

Pro Tip:
Opt for a pop color like one of this season's “it” shades – pink! – when pairing with a neutral look.

What Shoes to Wear with a Maxi Dress: Sneakers

The Bottom:
Mckenna Midi Dress

The Shoe:
Gola Elan Sneakers

Why It Works:
Sneakers bring down any overtly feminine dress to read more casual and cool.

Pro Tip:
If using a tried-and-true retro sneaker style, make them a statement piece.