Lug sole boots are a great fall into winter option for footwear. But once the shoe game changes, it can be a huge struggle to figure out what’s going on with the rest of the outfit. Here are a variety of silhouettes to pair with lug sole boots for the season. You can add to these combinations to make these looks your own, obviously, but these are my tried and true formulas with lug sole boots that work!

My lug sole boots are the (water resistant) Brooke Boot from Freda Salvador. I find these lightweight boots to be true to size (unless you’re wearing with thicker socks, then size up 1/2 a size). I almost always pair mine with these super cozy, comfortable cashmere socks (also a Freda find). Use code 15CONNI for 15% off your first pair.

Full length STRaight leg jeans or pants

The width at the bottom of the full length straight leg allows for the lug sole boot to sit right up and in the wider part of the leg, which is a great balance of pant length to boot.

Sweater // Ozma of California Gia Sweater (code CONNI15 for 15% off any Ozma pieces) - fits true to size and is an alpaca blend.

Jeans // Rollas full length jean - fit true to size

Bag // Clare V Petite Henri (they often sell out so keep your eyes peeled for a relaunch)

Ankle length slip dress

A fuller length dress with width at the bottom helps to elongate the frame and draw the eye down and out. You can see an example of this here.

Slip Dress // Max Mara - fits true to size (comes in olive green too) and has been low in stock

Cardigan Sweater // Sezane Achille Cardigan

Bag // Clare V. Sac Bretelle Black leather Bag

kick crop flare

A kick crop flare jeans functions like a flare only not quite as long, so the narrow boot shaft shows, which works well to elongate the frame.

Jeans // Citizens of Humanity Crop Flare jeans

Jacket // Quilted puff cropped jacket Nordstrom

Bag // AllSaints Tote

Necklaces // Thatch Jewelry

Full length flare jeans

Jeans // Full length & Other stories patch pocket jeans and these are similar in blue denim

Sweater // Frank + Eileen (they’re having a weekend sale here)

Wide Leg Pant

Pants // Vincent James Wider Leg Pants (a suuuuper comfortable 100% merino wool repurposed pant)

Jacket // Quilted puff cropped jacket Nordstrom

Puff Sleeve Sweater // Sold Out NYC just enough puff sweater - code CONNIVIP15 for 15% off or through the weekend code use code LIMITED20 for 20% off any of my favorites on that collection page.

With a full length coat + Trouser pants