New boots make everything better

Perhaps you didn't notice, but I wore the same pair of new Frye Cindy pull-on boots in my outfits during the DEATHMATCH. They were full price at Nordstroms and they looked fantastic in the store. The true test came when I tried to pair them with my dresses; they failed miserably. They were too short for my long leg, and the trendy scrunch look is not appealing to me. Back they went this Friday!

Today, my friend Jessie were out to brunch with plans for some direct-strike shopping afterward (I had a couple of specific pieces that I wanted to shop for). Impulsively I added another stop at the Von Maur next door to the restaurant, where I found a stunning, STUNNING pair of Franco Sarto riding boots. They're so sleek on, perfect for my long calves and dressier style. And about HALF the price of the Fryes I returned!

We headed to our next destination, Ann Taylor, where I had a 40% off coupon for one-full price item, and a deep urgent need to see this dress in person. The dress was even more amazing close up; "dark plume" is a rich dark blue, almost slate but inkier. And it has pockets!



YOU GUYS. YOU WILL PRY THIS DRESS AND THESE BOOTS OUT OF MY COLD, DEAD HANDS.



Keeping them, keeping them, keeping them, OMG I am keeping them. The boots are perfect for dresses and skirts, which is my primary outfit choice these days. But for jeans I still needed to keep looking.

Thus, our last stop was DSW; I wanted to check on another pair of Fryes (the Paige Buckles) with which I have a long and storied history. I bought them last year at Nordstroms with Shopping Friend (who got them in black), but I could not work up the nerve to wear them in the end, so they went back. But a piece of me regretted that choice, and when they showed up at DSW this season (at about $150 less than what they were at Nordie's) I fell in love all over again. I've hemmed and hawed and tried them on at two different stores, but told myself the other Fryes were better and I should stick with those. Since Fryes #2 were now out of the picture, today I gave Fryes #1 another chance. The browns were gone, and I had resigned myself to the blacks, but when I opened the size-nine box, they were brown. I told Jessie it was fate; she rolled her eyes at me but did agree they were awesome boots and I should get them too.

So I did. Here's the rub: I am STILL not sure if I should keep them. I don't have a good eye for wide, casual boots, the kind you are supposed to wear over jeans. What is it supposed to look like? This?



Help! These are my questions:
Should I tuck the jeans in better so they don't scrunch at the top?
Is there something I should do to keep them snug? (I already had a pair of knee socks on over the jeans...)
Do I look as much like an ice cream cone as I think I do?

And then you can see them with a dress.



Is that what it's supposed to look like?
Is the fit right? I could fit my whole hand in the top; isn't that too much?

I would love, love, LOVE, to keep these but I feel just as uncertain and overwhelmed by them as I did last year. This isn't a look I am used to, and I have no idea if I am doing it right. I would like to be able to master it if I could; it's cute and fun and I think I could blend it into my own style. I just have to get more confident about it.

Any suggestions? Thank you!