Hellobee Boards

@LindsayInNY: Ooooooo!!! Gotcha... okay! Depends on the outfit... a pair of pointy toe pumps?

I wear these two with jeans -- the top pair is from Target, bottom is Clark's Indigo. I like them because they also go with dresses

If I'm doing a more flared-leg jean I'll wear a stacked heel or high wedge. Skinny jeans I'll usually wear a thinner heel like a stiletto or sometimes a stacked heel as well.

@MrsSCB: I have the bottom pair from Clarks and they look awesome with skinny jeans.

@LindsayInNY: Are you pairing this with skinnies or flares? With skinnies, I'd go with a pair of velvet material pumps like this pink pair: https://www.madewell.com/AST/Navigation/Sale/AllProducts/PRDOVR~29097/99102872175/ENE~1+2+3+22+4294967294+20~30~P_new_to_sale%7C1%7C%7CP_priority%7C0~20+17+4294949633~15~~~~~~~/29097.jsp

With flares, I'd go with wedges or a sleeker boot like this: https://www.madewell.com/madewell_category/SHOESANDBOOTS/boots/PRDOVR~03901/03901.jsp

@LindsayInNY: The new shorter wedge boots would look great with flares and skinnies.

I've had good luck with the Seychelles brand since they often have a nice thick heel and are comfy. I like many of their styles with bootcut jeans and flares.

I'm digging this pair right now.

http://seychellesfootwear.com/Home.tpl?page=singleitem.inc&cart=13102152745&sku=allsmil9sl&H_P_Special=allsmil9sl#

I actually really like to wear dressy heels with jeans, not chunky heels, but more like stiletto heels. Back in the day (pre-baby) I used to wear heels pretty much every day, to the point that I once went out with coworkers wearing flats and they were like "you're so short!".

The only ones that I ever wear are a few years old. But, they are silver t-strap with a thick heel and a round toe. They are comfortable and I can wear them all night when I am out at a bar (which honestly has been a while). But, I also really just love the look of a pointy toe pump with jeans, but not for everyday. I don't wear heels with jeans unless I am going out somewhere.

@LindsayInNY: I think Naturalizer is a great place for comfortable heels. They have awesome shoes. They just get a bad rep because people think they are "old lady" shoes only because they market themselves as being comfortable.