46 Street Wear Casual Chic Outfits Trending Ideas

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You need to know what dresses to wear with skirts? You’ve come to the right place. Nothing is worse than leaving the house with “The Creeper Outfit.” You put on a dress with boots and you think it is sort of cute, but as the day continues, the sensation of being horribly dressed slowly creeps over you. You arrive at work and no one makes a comment about your outfit. You go out to lunch and you get a weird look from someone the next table over, and the next thing you know you are in the bathroom mirror in a panic trying to figure out how to “fix” your outfit. However, by then it is too late; you are already a victim of The Creeper Outfit, and your confidence for the remainder of the day is shot. We are going to fix that right now and give you some ideas of dresses and boots that can be paired together.

First up is the midi-length tube dress and knee-high boots. This look is great if there is a chill in the air because it covers up your entire lower half. The midi-length dress or skirt is one where the hem hits in the mid-calf area, so that the dress will cover the top half of the dress. If you want to see this look in action, check out Rene Russo in The Thomas Crown Affair. She wears a black midi-length tube skirt with black knee-high lace-up boots.

Next is the long maxi-length dress with riding boots. This is a really casual look and a little country; however, you can make this a little more high-end chic country estate by wearing a long floral print maxi dress with brown riding boots. Use accessories to dress this up or dress it down.

The next option is only for the brave of heart who are extremely comfortable with their body, and more importantly with their thighs. This look is a mid-thigh shift dress with over-the-knee boots. The shift dress is loose-fitting, so it keeps the outfit from looking too street-walker. It exposes just a little bit of thigh from the top of the boots to the hem of the dress. This look is now very on trend, but very few can confidently pull it off.

Your knee-length summer dresses can also enjoy the company of boots with cowboy boots. To match a lighter summer color palette, consider brown, tan, or gray cowboy boots. This is a great complement to a summer outfit; however, if you have big calves, be cautious of this look as it may cause your lower half to look heavier than it actually is.

Last but not least is a great look for work: a simple sheath dress with high-heeled knee-high boots. In fall and winter, wear this look with tights for warmth – additionally, if you are less confident about your legs, tights can help keep everything together and prevent excessive jiggle.

These dress and boot pairings should keep The Creeper Outfit at bay


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