By now all the toe bearing shoes have gone into hibernation and the booties, pointed toe heels, and OTK boots are free to roam. Recently, a shoe loving  twitter follower posed the question: "What's the best way to wear booties/ankle boots with skinny jeans?" It's a good one and one that was answered this weekend when the bff and I took a day trip to Santa Barbara.

You've got two options: roll or tuck* 

 { sole society booties // steve madden moto boots}

Typically, I go for the roll with booties that have some type of v or ankle exposing cut as it's very flattering. The tuck comes in handy with actual ankle or moto boots. If you feel like the tuck cuts off your legs, match your boots to your denim (ie: black boots & black skinnies) to elongate the leg.

Want more ankle boot x skinny jean inspo? Check out some pinspiration on my ' Falling into Fall'  board.

About that Santa Barbara trip...
If you're planning a day trip to SB and just happen to enjoy a glass of wine or four,  I highly suggest doing the Urban Wine Trail. The trail gives you the opportunity to taste some amazing wines from Santa Barbara County's finest all within walking distance of each other.
Municipal Winemakers is my absolute fave but nothing beats the view at Deep Sea.
 Gorgeous! Here's another incredible shot on insta. Of course, there is also great shopping on State St. which I totally took advantage of (surprise!) as noted in Monday's post.

*unless you're super tall and can do the crop!