Inspiration, Style

How to Wear Ankle Boots: Styles & Outfits (Part I)

Ankle boots and booties have become autumn’s favorite footwear and a key piece in fall outfitting. But trying to figure out what to wear with booties can sometimes take more thought and planning.  I think many of us get stuck in a rut and just throw on the usual skinny jeans because that’s what’s always been done and it’s an easy go to.

I was recently asked if I could do a blog post on how to wear ankle booties. Having styled some looks of my own and done some research on all the types of booties out there, and there are many,  I thought I’d break this post up into a three part mini series. I’ll be covering the most common styles: the wedge, the block heel and the heeled ankle bootie.

This week’s post will cover the wedge ankle bootie. I’m going to show you how best to style your booties and make them work for your wardrobe. You can use these outfits as a guide and inspiration for your fall repertoire.

The Wedge Bootie | Low and High

The weather doesn’t get much cooler in fall here in Florida. The months are all that really change. But a wedge ankle bootie in brown or black suede add warm texture and certainly has the look of fall.

the park

Flat or low ankle booties have a more casual, boho-chic look. Just recently I’ve gotten into wearing boyfriend jeans. I often find them to be frumpy looking. But the slim boyfriend jeans pair well with the casual, low wedge booties. I’ve grown to love my Coclico’s  more and more. I wasn’t sure how flattering they’d look on me but I wear these a lot in fall, especially with shorter dresses.

Style Tip 1: Because boyfriend jeans tend to sit lower on the hip and have a wider pant leg, I leave about 2 inches of space between the bottom of my pant hem and the top of the bootie. You don’t want your legs to look shortened or chopped off.

Style Tip 2: With boyfriends jeans I typically like to style v-neck tees and this flute sleeve top with a tied knot on the side for extra style and fit. Try it!

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Style your booties with a short, lightweight dress layered with a knit vest over top. I love this outfit. It’s my seasonal go to! This is a great example of how you can dress up your low wedge booties.

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Low wedge booties can also update last season’s favorite floral or lace dress. Just throw on a jacket and viola, you have the perfect fall outfit! How cute is this lace dress with that olive green jacket?

Style Tip 3: With a lower ankle bootie, you want the hem of your dress or skirt to fall above or just below the knee to keep a longer leg line.

Shoe Recommendation: Sam Edelman Petty Bootie (ON SALE)

Higher wedge booties have a slightly dressier look to them and usually come higher up on the ankle. Two best ways to style these types of booties are to wear them with cuffed skinnies or with leggings.


Depending on how slim-fit your denims are one cuff or two cuffs are the general rule to wearing skinnies with your booties. If you try tucking your pants in your shoes they often pucker and look funny.  You generally want to leave an inch of space between the bottom of your pant and the top of your bootie. Just enough to expose your ankle.

Nothing says cozy like a knit poncho. I don’t see many of them worn but I think they can add sophistication to an outfit. As it does here, worn with my cuffed skinnies and high wedge booties. This outfit is perfect for traveling! I plan on packing this ensemble for my trip to Kansas and Nashville this November.

Style Tip 4: For longer skinny jeans a larger cuff (2-3 inches) looks best.


Some people shy away from wearing ankle booties because they feel it makes them look choppy. But tucking your leggings or tights into your booties actually elongates your legs and creates a seamless look. The key is wearing the same color, black on black. Stiletto or heeled booties are best for evening wear but I styled this outfit to show you how a high wedge bootie can also work for you at night. Here I’m wearing them with a graphic print Salaam dress. This outfit is more street-chic and city.

Shoe Recommendation: TOMS Desert Wedge









Fall Fashion Inspiration: Casual Elegance

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I fell in love with this dress the moment I saw it through the storefront window of a local boutique. When you find a dress as unique and striking as this one, you’ve gotta grab it! This navy and white striped, hi-low ruffle dress is 100% cotton. The ruffle details and dramatic train takes things up a notch. This ain’t your typical cotton attire! The cascading ruffles are playful and flirty. The back tail moves beautifully as you walk and adds elegance. The long sleeves have a slight puff to them with ties at the wrist. Both trendy and on-point. This fall the red day bag is the new neutral and staple piece to have. This red leather Furla handbag is the perfect size and pop of color against the navy and white stripes. The silver chain and circular detail on the clutch is more contemporary which updates this more classic dress. For a laid back everyday look, you can easily wear this dress with a pair of wedges and red tote bag. This head-turner is best worn for a special daytime date or wedding occasion. I felt like Scarlett O’Hara in Gone With The Wind during this photo shoot. A belle from the south.

Dress $56 – Found at the charming and pretty shop, The Hen House! Pop on in to shop one of a kind artisan items and local fashions. Tell them the Window Shopping Diva sent you! You’ll be inspired and fall in love with this new boutique, located in Carrollwood, just as I have.

*I recently found a similar dress  on clearance at – Women’s Ruffle Wrap Dress – Who What Wear Blue Stripe

Furla Clutch $45 – You can shop for this luxury handbag on my eBay shop by clicking The Window Shopping Diva.