How To: Style Booties

This week for my how-to series, I'll be covering how to style booties.  I love my booties and have been living in them this fall and winter!  They are such a great trend this year, but I'll be honest, styling them can be a little daunting at first.  Today I'll be sharing six ways I like to wear them.

• Booties can be a little more casual in nature, so when styling them you'll probably find they look best styled with more casual pieces.
• First, I'll be styling it with a dress and tights.  I love this combo and it seems to work best with cotton or jersey dresses.  Wearing black tights with black booties, or brown tights with brown booties will also elongate your legs, which is always a plus!
• The second way I'll be styling it is with long leggings.  I love this for a casual weekend look or a night with friends.  Tip, if you're leggings aren't quite long enough, wear black socks and tuck them into your leggings, no one will know the difference. : )  
• The third way is with boot-cut jeans. Just add either one big cuff or cuff it twice and just let the bottom of the booties show.  This is a great way to transition into booties if you're just starting to get comfortable with them.
• The forth way is with a pencil skirt or mini-skirt and bare legs.  I think bare legs and brown booties are are better combination than bare legs and black booties.  Black booties and bare legs can have a tendency to cut you off at the ankle and make you look shorter and wider than you are.
• The fifth way, and my favorite way to wear it is with skinny jeans.  You can either do one bigger cuff or cuff it twice.  The little bit of ankle that shows is super flattering.
• The last way is with tights and a mini-skirt.  This works great for both brown and black booties and if perfect for when you want to wear a skirt in the winter.

Also, a few days after I got this post ready the lovely Sarah at Sarah's Real Life created a post on how to style booties too, check out her post for some more great tips. : )

I wore this outfit on the blog here and love how the booties work with this look as apposed to a normal heel. 

Cardigan: Banana Reublic $7 (thrifted with tags) similar

Dress: $5 (thrifted with tags) cute option

Belt: The Limited $5 similar

Scarf: Craft Show $10 cute option

Bracelets: Stella and Dot Renegade, Urbane

Tights: Esprit $5 (via TJ Maxx)  similar

Booties: Jessica Simpson $37 same

I love this outfit and wore a similar one here when I discussed how to style a boyfriend cardigan.  Like I said then, I don't think leggings are appropriate for work, but I love this for a weekend look or a night with friends.

Cardigan: Target $12 same / Target Coupons

Scarf: Boutique $15 exact

Chambray: Gap $15 same

Leggings: Target 

Booties: Jessica Simpson $37 same

Here I'm wearing it with my herringbone vest.  I wore it similarly  on my how-to wear a herringbone vest post.  

Vest: Coldwater Creek (can't find similar anymore)

Sweater: Loft $30 same

Scarf: Joe Fresh $10 similar

Bracelets: Stella and Dot  Chimera, Moxie , Renegade 

Jeans: Old Navy $5 (thrifted) similar

Booties: Jessica Simpson $37 same

I wore this outfit on the blog here and it was one of my first attempts at styling booties with a skirt.  I love how this combo came together and these booties are probably the best pair of shoes I've ever owned.

Cardigan: Loft $5 (thrifted) similar

Top: Loft c/o Chippmunk similar

Skirt: Loft $40 c/o Chippmunk same

Belt: Kohl's $1.5

Necklace: Stella and Dot same

Bracelets: Moxie , Renegade Stella and Dot

Boots: Wanted $29 (via eBay) similar / same in black

I wore a similar outfit on the blog here, however instead of wearing jeans I wore a skirt. I've today's look in my head for a while, so I'm glad I can show it today.

Blouse: Target $20  same

Vest: JC Penney $8 similar

Belt: Kohl's $1.5

jeans: Old Navy $19 similar

Belt: $1.5

Necklace: Stella and Dot same

Bracelets: Stella and Dot  Chimera, Moxie , Renegade 

Boots: Wanted $29 (via eBay) similar / same in black

I showed you this outfit on my how-to style a boyfriend cardigan post here.  I think that wearing tights with booties is definitetly a great option once winter hits for sure.

Cardigan: Target $12 same / Target Coupons

Top: Loft c/o Chippmunk similar

Skirt: Loft (thrifted) cute option

Necklace: Stella and Dot same

Leggings: Target

Booties: $29 (ebay) same in black