Booties season is around the corner.  Yes, booties will remain a hot trend for this upcoming fall, despite the fact that, while women love to look at them, many are confused about how to wear them.

I received an email from a reader asking for help on how to wear booties.  As she asked me in her email (which made me chuckle a bit, particularly the string puppet comment):

There is something I’d love for you to cover in a post: how to pull off wearing booties. (The decent kind; not Uggs or anything slipper-ish.) I see them on other women all the time and they look great, but when I try them on, they either make my feet look huge (giving me a dangley string puppet look), or make my legs look short and chunky. I am 5′ 8″, a size 10 in pants/dresses, and size 11 in shoes – are my feet just too big to pull off booties? Or are there better ways to style them?
Anyway, just an idea, as we get closer to fall!

Let’s all learn how to wear booties, shall we?

There are a few ways to make booties work, and in  today’s Accessorized 5 Ways I am going to use these Steve Madden booties to show you how to do it.  Before I get into my tips and outfits below, I want to share a photo with you of a client who tried on two pairs of booties.  It was quite amazing how the shape of each pair made her feet look completely different in length and width.

Screen Shot 2014-08-05 at 11.44.13 AMIt’s almost hard to believe that these two feet belong to the same woman, and this is why it is important to choose the right shape and style of booties first.  Like the reader who asked me the question above, this client has very large feet and slim legs.  The booties on the left make her foot look smaller because of the rounded toe and the horizontal lines that cut across the toe and ankle.  On the right (her left foot) the pointed toe and vertical, unbroken line down the middle of her foot makes her foot look leaner and longer.  When choosing booties it is important to think about what you want your feet to look like in them.  For example, I am built the opposite of my client, I have large ankles and calves and very small feet for my tall height.  If I were to wear the shoes on the left my feet would look like stubby blocks.  Part of the reason the reader who feels like a “dangley string puppet” might be because the booties she is trying on are making her feet look longer and bigger than they already are (just a guess).

The next question to ask yourself is how you plan on wearing a pair of booties.  Using myself, again, as an example, I look ridiculous when I wear booties with skinny jeans.  Between my heavy legs and little feet, when wearing skinny jeans my thighs look super huge.  I need booties that have more bulk to them and aren’t tiny and streamlined.  I also tend to wear booties with tights that match the color of the booties and short skirt or dresses to create a longer, leaner line and so my legs don’t look chubby.  I choose styles that are big enough around my ankles so my fat calves don’t look like squeezed sausages.  In addition, a wider opening of the booties makes my legs look thinner.  With all the different styles out there, thinking about how you plan on wearing a pair can help you cull down and choose the right styles for you.

How to wear booties

In addition to body issues when wearing a pair of booties, the question of what to wear them with is another big issue.  Do you tuck your pants in?  Do you wear them with trousers?  What about skirts? And so on.  Below are five ways to wear booties that will not only give you some styling ideas but also help you decide which style might be right for not only your lifestyle but your body shape.

Outfit #1- With a short dress

A way I find booties to look best is with skirts or dresses, particularly when worn with dark opaque tights that match the color of the booties.  The reason why this works is because a long, monochromatic line is created between the legs and the feet.  This is a great solution for women who have short legs, large ankles and calves or are petite.

In this outfit, I paired these booties with a purple dress from Boden, a printed scarf, Max & Chloe earrings, a brown handbag from Kate Spade and Spanx Tight-End High-Waisted Tights in Bittersweet.  I particularly love these tights because they are seriously indestructible.  I had one pair for years and they accidentally made it into the dryer on several occasions.

Outfit #2- With skinny jeans

Okay, the big question, what do you do with your skinny jeans when wearing booties?  There are two ways to wear skinny jeans with booties.  The first way is to tuck them into your booties if they are higher and less shootie (shoe booties) looking.  The second way is to let them scrunch up slightly around your ankles.  It all depends on the type of booties you are wearing.

With this pair of booties and these skinny jeans from J. Crew I would tuck the jeans in.  This outfit is styled casually with a grey boyfriend cardigan, graphic Modcloth t-shirt (that has foxes on it!!), orange and turquoise earrings, a teal bracelet and bright orange Coach handbag.

Outfit #3- With a skirt

Booties and a skirt work for the same reason that a dress and booties work, particularly when wearing tights and booties in darker colors of the same shade.  A longer, leaner leg line is created vs. the legs being broken up with booties that cut across your ankles.

In this outfit I styled the booties with a printed skirt, brown MICHAEL Michael Kors top, zipper vest (that gives the waist some shape), an Anthropologie pendant necklace and Vince Camuto handbag in a soft sage.  Depending on your work environment, and outfit like this could easily go to the office and would be a great dressy weekend look.

Outfit #4- With boyfriend jeans

You see other women wearing boyfriend jeans and booties, so why do they look so stupid when you wear them?  It’s not easy to pull off boyfriend jeans and booties and it isn’t for everyone.  I think there are a few tricks to pulling this off well.  First, I think you need to have slimmer ankles and calves because some of your skin might show.  Second, you have to watch how baggy your boyfriend jeans are.  A slimmer pair will probably work better.  Third, you have to find the perfect length of boyfriend jeans to wear with booties.  You don’t want to look like Oliver Twist in booties and cropped boyfriend jeans.  Try to have the cuff of the boyfriend jeans graze around the top of the booties or just slightly higher.

If this look is for you, here I styled a pair of boyfriend jeans and these booties with a grey turtleneck, cropped tweed Boden jacket, a taupe Big Buddha handbag and grey and taupe earrings.

Outfit #5- With a maxi skirt

Another way to style of booties is with a maxi skirt.  It’s probably the safest way to do it only because nobody will see your legs, plus, booties may be more comfortable under a maxi than a tall pair of boots.  If a more relaxed, slightly Boho look, is your thing, and you are channeling Stevie Nicks that day, this may be something to try.

In this outfit I took a printed maxi from Alice + Olivia and styled it with a denim shirt from J. Crew and belted the waist with a Steven by Steve Madden belt.  Lastly, I wrapped a navy scarf around the neck, added a pair of gold stud earrings and brown Brahmin handbag.

Can you wear booties with trousers?

You may be wondering if booties can be worn with classic work pants and trousers.  Yes, absolutely.  I just didn’t style them that way here because the booties style I chose for this post wouldn’t work.  When choosing booties for work pants avoid a lot of ankle straps and details or booties with wide openings which will only get caught on the leg of the pants.  Instead, shooties or cleaner booties with slimmer openings will be the better choice.

Shop for booties

Now that you have some more direction on booties styles.  Check out the ones I found from around the web.