Please help the hopelessly fashion challenged

[ginap]

*waves hello from Frumptown* I am trying to mix up my look a bit and need some help.
A.  Should I pull the trigger on these booties in black and taupe -
B.  If the answer is yes, what next?  How do I wear them?  Can I wear them with tights and a dress?  Can I only wear them with skinny jeans (because I can't find a pair that doesn't look hideous on me).

[pizzapizza]

I think they are cute and yes you can wear them with all the above. What is your lifestyle like? Would it make sense to get one pair of the ones you pictured and another different pair in a different color.

[jenniferl923]

I have the taupe. I ordered the black and returned them as I didn't feel they were working for my wardrobe but I've seen them on other people and they are cute.

I wear with dresses and jeans. They are super versatile IMO.

I also have these in taupe-

www.toms.com/women/taupe-suede-womens-lunata-booties

- for when I want to be a little dressier but I can wear them interchangeably with whatever I would wear with the wedges. They are actually just as comfortable. They are my new favorite shoe right now.

You could do one wedge in one color and one of the heeled in the other.

[jenniferl923]

And also idk if you've looked, but when I love an item of clothing and need help styling it, I go to Pinterest. Try looking for "booties with dresses" or "booties with jeans". It also helps me remix my faves.

[ilovebed]

I have the black ones...in the older style with the little toe fold thing. I wear them all. the. time. They are so comfortable. I wear them with leggings and tunics and with cuffed skinny or straight leg jeans. This is the third cold season that I've had them and they are still in great shape.

[ilovebed]

Also, why do you think skinny jeans look hideous on you? I personally can't really do skinny jeans because my calves are really big so they just don't look right. But I wear the Gap Real Straight jeans instead which are really comfortable and flattering on my curvier frame. I'm usually wearing those with my Tom's. Cuffed.

[xokell2]

Do it! So many options

[xokell2]

[xokell2]