Free Standard Shipping on all orders $65+

Spring dress with booties

Cute Booties to Wear With Dresses & Skirts All Year

Boots may be made for walking, but booties can also really take your wardrobe somewhere special—especially when you pair them with a dress.

Finding the perfect booties with dress energy takes finesse, though. While it’s a style that rocks every season of the year, there are (as always) tips and tricks that’ll really help you keep that “oooo!” in booties.

Welcome to bootie-camp, ladies. This is the francesca’s flash course on how to wear booties with a dress—during every season. Like all fashion advice, though, it’s not as much definitive as it is suggestive. If you have some kind of bootie/dress epiphany of your own, post that fire and tag us!

Let’s do this.

General Rules for Wearing Booties with a Dress

No matter what season it is, there are few booties with dress rules that stay the same.

  1. The dress itself usually acts as the centerpiece of an outfit. Try to pick a boot that complements, but doesn’t overpower the statement the dress makes.
  2. For more elegant dresses, sleek and heeled ankle booties are usually a good starting point. The more casual the dress is, the more a flat and comfy bootie will make sense.
  3. If you’re rocking a dress with intricate or elaborate patterns, even out the energy with simpler booties. If the dress is simple, add some edge with a wilder pair of booties.
  4. More casual, light booties make sense in the day, while the best booties for evening wear are generally sleeker and darker.


For the most part, rules like these hold true when you’re choosing which dresses to wear with booties. Now let’s look at the booties with dresses pursuit from a seasonal perspective. Skip to whichever season it is you’re reading this!

Winter: Perfect for a Sweater Dress with Booties

During the fall and winter, booties provide the perfect opportunity to pull together outfits that are total fire, even while it’s freezing. Booties can act as an anchor during colder months, and a great option for keeping things chic as you wait for spring.

Obviously, colder weather carries with it sweater dresses, and yes—it’s totally cool to wear a sweater dress with booties. Just keep in mind the suggestions above. A busy sweater pattern may suggest a sleeker bootie.

Tights are also on the table. It’s usually a good idea in winter to match your booties with your leggings for a warm, sleek look. Black booties always look great with black tights, and can even make your legs look longer. The same can be said for other dark colors like brown or burgundy.

Since it’s colder during those winter months, chances are you’ll be reaching for a midi dress rather than a mini dress. The midi hem is going to hit the middle of your calf—to keep your leg line looking long, choose booties that go no higher than your ankle bone.

Spring: Dresses to Wear with Cute Booties in Spring

When the ice thaws and the flowers are blooming, the booties with dress combo can take on a whole new edge. Here are some tips for pairing booties with dresses during the Spring.

The good news is that the booties you may have worn in the winter can still look great with a floral dress and bare legs. Those same sleek black booties you wore with tights while it was cold can be used to anchor a new dress when it starts getting warmer.

But while black will still work, it’s usually a solid idea to have some brown and light-colored ankle booties in your wardrobe for spring. When choosing which dresses to wear with booties, you’ll find lighter booties complement a whole range of dress styles, from tea dresses to wrap dresses.

Since you’ll be showing your bare legs again, it’s also a good idea to grab a pair of booties close to your skin tone. A bootie that matches your skin tone can be paired with nearly any dress to create a perfect line from hem to heel.

If you really want to spice spring up, try some cowboy booties. You’ll probably be outside more considering it’s warmer—western-style booties can bring a casual, fun tone to your booties/dress outfits.

Summer: The Short Dress with Booties

Obviously, there is a good amount of roll-over between spring and summer when it comes to booties and dresses. In summer, you can definitely dial up the brightness by keeping those lighter boots in rotation and continuing to pair them with patterned, printed dresses and mini floral dresses for a stylish vibe.

Keep those brown booties handy, or even get some new styles of brown booties, like lace-ups or chunky fit. You’ll find they match with all kinds of summer dresses, and provide almost endless opportunities for slaying your game in the sunny season.

Another great angle for how to wear booties with a dress in summer is to tap into more casual styles of booties. Chelsea boots can provide a laid-back, yet fashionable look when paired with mini dresses. A more rounded toe will give you that low-key cool, and a flat heel will keep you comfy.

Since you’ll be showing more leg during summer, experiment with different boot shaft heights. A short dress with boots might make your legs look short or strangely long if the boot shaft isn’t suited to compliment the dress. Have fun, but be savvy!

Fall: Wearing Dresses with Booties in Autumn

As the air starts to cool again and summer slides into fall, you’ll still be able to slip into a pair booties with your dresses. It might be time to move those lighter hued boots to the back of your closet, though, because autumn is going to want darker brown and black booties.

Chances are, you’ll want to start cycling tights back into your rotation as winter approaches, so remember that pairing booties with matching-colored tights is always a good move. You can even experiment with pairing darker booties with patterned tights for an edgy autumnal outfit.

Like winter, fall provides that wonderful opportunity to pair a sweater dress with booties as well. For bouncing around town as the leaves fall, a flat-ankle bootie goes great with casual dresses like a T-shirt dress, a skater dress, or a sweater dress.

Cooler autumn weather may also make you want to mess around with maxi dresses, which is fine, just try to hem it so it hits right above your ankle. To lengthen and add dimension to your legs, try a style with a slit up the side!

That’s it for bootie-camp this time around! Since fashion is always changing and this is francesca’s, we’ll keep our ear to the ground for any juicy updates to the booties with dress angle.

For now, since you’re a new expert on how to wear booties with a dress, keep gunning and stunning with all the amazing possibilities. No matter what season it is, throw on some booties and dress to express—it’s your prerogative.


Jump To:

Leave a Reply