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Wear the trend: Boots with dresses

Boots and a dress can be a tricky look to get right. Which boots look best with which dresses? Should you opt for heels or flats? No matter what questions you might have about pairing fall’s best boots with your go-to dresses, we’re here to help you master the trend.

Boots and dresses: Tips to consider

If you’re stumped on how best to work the boots and dresses trend, we’ve listed some simple style rules to keep in mind.

  1. Ankle boots and long or midi-length dresses are a great option for fall.
  2. Leave some skin (or tights) showing. You should be able to tell where the dress ends and the boots start.
  3. Don’t be afraid to add patterned tights to your look. Heavier fall boots lend themselves well to sassier legwear.
  4. Sweater dresses were made for boots, especially slouchy or motorcycle styles.
  5. Don’t be afraid to experiment. Try out a few different styles of boots with various dresses to see what works best and what you love most.

4 Cool looks we love

Check out some of our favorite boot and dress combos for fall.

1. Look one

Look one

Pair this short and sweet tartan knit sweater dress ($180) with leather piping and adorable pockets with these sumptuous gray suede mid-booties ($328). The look is effortlessly chic but still casual and comfortable enough for weekend wear.

2. Look two

Look two

Pair this easy-wearing sleeveless shift dress in a gray cable knit ($90) with these classic black leather riding boots ($160) for a look that’s ready for anything. A shift dress lends itself well to riding boots since they’re both structured, which makes for an ideal switch from the flowing, looser looks of summer.

3. Look three

Look three

Pair this simple but chic green jersey Nanette Lepore sheath dress ($328) with some black suede round toe ankle booties with a slim stiletto heel ($129) for a streamlined seasonal look. The delicate ankle boots work well to balance out the heavier nature of the sheath dress. Add a pair of opaque black tights for a classic, office-friendly look.

4. Look four

Look four

Pair this cute, colorful column dress featuring flattering stripes in fall-ready hues ($100) with a pair of sleek knee-high wedge boots ($240). Add a boyfriend blazer or denim jacket and textured knit tights to build a stylishly seasonal ensemble that works for the office and into evening.

More style tips and trends

Trendspotting with Jill Laine: Summer-to-fall style
Fall’s biggest fashion dilemmas — solved
Heidi Klum exclusive: Her new clothing line

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