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General Dress & Boot Guidelines
Before we start pairing up, it’s important that we go through some general guidelines:
Know What Kind Of Look You’re Going For
If you’re not sure about what to wear with your boots, just think about the vibe you’re going for. Keep in mind that any bootie whose heel is three inches or above is going to have a dressier look to it. A pair of sleek high-heeled stilettos paired with a black dress is perfect for a more formal occasion, while you could opt for a pair of chunky ankle boots with the same short dress for a casual look.
Make Sure That Your Colours Go Well Together
Choose dress colours that match your boots and vice versa, but avoid strict colour matching. It would be a waste to wear one solid colour from head to toe when you can contrast and complement the colours of your outfit. For example, you can pair up nude or brown boots with a bright dress with a bold pattern.
Make Sure The Colours Don’t Compete With Each Other
When picking dresses to wear with your boots, the goal is to let your clothes complement each other! Try to opt for footwear that contains a colour found in your dress. If you have a black, pink, and purple sundress, knee-high boots that have those colours will look good paired up.
Remember The Three-Inch Rule
Try to keep a three-inch gap minimum between your dress and where the boots end. It looks loads better when you show a little skin. Of course, there are exceptions to this rule, especially if you’re going for a more laidback vibe.
Boots To Wear With Dresses: How To Wear This Stunning Style
Ankle Boots With Dresses
Ankle boots are very versatile, especially since you can wear them with both long and short dresses. Whether you pair them up with formal or casual wear, a good ankle boot combination is going to turn heads! A good rule of thumb is that closed-toe ankle boots tend to be more dressy than its open-toed counterpart.
Shop this look: Lover Dress Ankle Boots by Jo Mercer, $259.95
Wedge Boots With Dresses
Not everyone likes the aesthetic of a wedge boot, but don’t knock this more casual, laidback style until you try it. Wedge boots are way more comfortable than their stiletto counterparts, so it makes for good daywear, especially when paired with a breezy floral dress. But with the right boot style (and a stunning cocktail dress), you can even rock this look at night!
Shop this look: Jav by Novo, $79.95
Stiletto Boots With Dresses
Thin, stiletto heels are not easy to walk in and they take a lot of practice to get used to, but boy do they look amazing! The high heel elongates your legs, which helps to balance out how boots often make you look “clunkier”. Because stilettos are slightly dressier, you can even wear this for more upscale events.
Shop this look: Rosana by Vizzano, $139.95
Long Boots & Knee Highs With Dresses
One of the best things about the colder months is that you can bust out your long boots. Pairing knee or even thigh-high boots with a thick winter dress is a great way to look chic while staying warm.
Shop this look: Lace-Up Peep-Toe Thigh-Highs by Missguided, $124
Cowboy Boots With Dresses
We love the cozy style of a good pair of cowgirl boots. These booties go well with all sorts of dresses, from high-slit dresses, trapeze dresses, shirt dresses, ruffle dresses, and many more. Any dress you pair with cowboy boots will automatically look a lot more rustic, so you can either go all the way with country dresses or contrast it with something more sleek and modern.
Shop this look: Indio by ROC Boots Australia
Dresses With Tights And Boots
Tights and leggings are the perfect accessories when you’re wearing boots. First, they keep you warm in the fall/winter months, allowing you to wear those fashionable short skirts and dresses even in the cold season. You can even jazz up an otherwise boring or monochromatic outfit with a pair of patterned tights.
Shop this look: Holo by Siren, $219.95
Whether you like it strappy and gothic or cute and cowboy, there’s a dress and boots combo for every occasion. Style it right (with the help of this guide!), and you’ll have a chic Insta-ready #OOTD for all seasons.