There’s a lot to plan when you’re spending a day out in Chicago. From what you’re going to do to how you’re going to get there, you’ve got a lot to plan. Unfortunately, many people make the mistake of not planning what they’re going to wear.

What you wear can make or break your entire day. It can cause you to head back early because your feet are sore, and it can cause you to spend more than you want on a sweater at a gift shop to stay warm.

If you’re planning a stay in the Windy City, make sure you’re ready from morning until night by dressing just right.

Don’t Shy Away From an Outfit Change

What you’re doing early in the day is likely to be completely different than what you’re doing later in the day. For example, if you have reservations at an upscale restaurant, you don’t want to wear a dress and heels all day long. Instead, embrace the outfit change.

Wear leggings in the morning when you’re out for a run, switch into jeans when exploring the city in the afternoon, and wear a dress when you’re ready to head out at night.

An outfit change doesn’t mean you have to carry a duffel bag around with you all day long! Chicago luggage storage can be found throughout the city. That way, you can drop your stuff off at a convenient location and change whenever you need to without having to carry around your wardrobe change.

Dress for the Weather

Chicago in the winter is very different than the summer. When you’re visiting will determine what you’re going to wear.

Dressing stylishly in the winter means wearing layers, but layers can also be an effective way to dress throughout the year. Morning and evening temperatures can be quite chilly, and having a sweater can help you get through those cold spots.

Don’t forget to check the forecast in the morning too. You may discover that the day is supposed to be quite chilly, even though it’s the summer, or it’s supposed to rain in the afternoon. Checking the weather will make sure you grab that sweater or that umbrella on your way out the door.

Be Mindful of the Wind

Above and beyond the weather, Chicagoans deal with more than rain and snow—they have to deal with the wind too. It’s important to remember that when you’re dressing for a day out in the Windy City!

For example, if it’s cold and you plan on wearing a scarf, it should be tucked into your jacket so it doesn’t get picked up by the wind. If you want to wear a hat, a low lying style is better than one with flaps, string, and pompom balls that can be whipped around in the breeze.

You have to think carefully about wearing that cute sundress too. If you don’t want to end up being embarrassed, choose a long maxi-style dress, or wear shorts or leggings under your skirt just in case it is taken by the wind.

Wear the Right Shoes

A pair of flats or sandals can make an outfit look polished, but they will do nothing for your feet if you’re stuck wearing them all day. Comfortable vacation shoes are a must if you expect to be out all day and night long without developing blisters or sore feet.

Choosing the right shoes will depend on what you’re doing during the day. For example, if you’re doing a lot of walking, tennis shoes are probably the best choice. If you’re heading out on the lake, consider athletic sandals instead.

Focus on Comfort

The great thing about Chicago is that vacationers and residents alike prefer to dress for comfort! That means you’ll fit right in when you wear things that you feel comfortable wearing.

You’ll fit right in when you wear:
  • Leggings
  • Skinny jeans
  • T-shirts
  • Sports team apparel
  • Capri pants
  • Shorts

It’s all about what’s most comfortable for you to wear. For example, skinny jeans may not be the most comfortable choice if you’re doing a lot of walking, while shorts may be a better choice for a day on the beach.

Don’t cut your day short because what you’re wearing is making you uncomfortable and sore. You can make it from morning until long after the sun goes down when you think carefully about exactly what you’re going to wear to make it through the day.