Travel Tips


Chicago which is known for its cold and snowy winters is one of the best cities in the United States of America to reside in, though sometimes, the weather can be brutal especially when there aren’t any preparations on how to tackle it. 

However, with the right tips as well as clothing layering guidelines, you will have a wonderful winter season while still looking warm and stylish during the coldest months to come.

To know more about how best to dress for the winter, then keep scrolling.

Understanding Chicago Winter Climate

The city of Chicago is known to have a very moderate climate with cold winters and warm summers. The average temperature rate in winter is about 26.4°F (-3.1°C) with an average snowfall rate of 28.1 inches (71cm). 

They experience the season of winter from the 21st of December till the 20th of March. So, if you are planning to visit Chicago either for a business meeting or deal, vacation or studies purposes with that period, then you should come prepared as you will be experiencing a temperature rate of about 30°F – 20°F degrees while if you will be staying till January and February, the temperature rate will decrease by a negative single digit.

However, during March and April, you will observe that the temperature will be increasing slightly to a rate of 40° and 50° respectively. Another thing that you should bear in mind that can occur within this month, precisely April, is that you might expect rainy days. So do well to prepare ahead of time to avoid surprises.

Dress For Chicago Winter

Having properly understood the climatic condition of Chicago, it is right that you know the different basic layering for dressing during the winter season in Chicago. 

During the winter season, there are different layers for dressing to prevent catching a cold or undergoing any future problems. Also, every temperature has specifically dressing that is required. These layers will allow you to enjoy maximum comfort throughout the period.

To properly get to know and understand these layers, we will discuss each of them below.

Read Also: How to Pack for a Cruise 

1. Base Layer

This is also known as a moisture management layer. This is the layer that is next to your body or your skin whose work is to move any form of perspiration away from your skin irrespective of the weather conditions and keep it dry. 

The good thing about it is that it will help to keep your body warm against any form of coldness or chillness from the winter.

In addition, the base layer clothes are made from the best fabric such as synthetic wool, silk, or bamboo fibres that can heat the body and keep it warm. 

So, therefore, you must avoid any fabric which can’t heat your body against cold and also can’t retain moisture. Some of these include cotton as they can’t.

Best Recommended Base Layer Materials

There are a wide range of fabrics to select from but the most recommended fabrics are those fabrics that can retain moisture and are quite durable such as polyester, nylon, or natural fibres such as Merino wool and silk.

Base Layer Weights

It is important that you opt for fabrics that are heavyweight or thicker as they will help to keep you warm and moisturized. So try and get one when you can.

Warm-Weather Base Layers

Below is some of the fabric underwear that can make you feel comfortable regardless of the coldness and what you should consider when getting them. They include

A. You should look for any summer shirt or outfit that has heavyweight. They are regarded as the base layer fabric.

B. Some shirts designed for warm weather spread the moisture out through the fabric, where evaporation helps with cooling. 

They aren’t regarded as the base layer fabric but they are the next-to-skin layer, they can increase your comfort in hot conditions.

C. Underwear like briefs, boxers and bras should also wick as well when you wear them during winter.

D. Look out for UPF-rated base layers as they will give you some added sun protection.

E. Avoid clothing made from cotton as your base layer wear. This is because they can’t protect your skin from the coldness of the weather. Rather, it is mostly worn when you are in the summer season.

F. Lastly, you can opt out of fabrics like wool as they will help to cool your skin as well as give you great comfort.

B. Middle Layer

This layer is also called the insulation layer. It is the layer after which you must have worn your base layer fabrics. They help to retain the heat that has been excreted from the body while maintaining the body’s radiation. It requires a fabric that can withhold the heat as well as keep your body warmer.

Best Recommended Middle Layer Materials

The best type of fabric for this middle layer is those that are much thicker and warmer at the same time. However, the best set of fabrics that meets these requirements includes woollen tops and others.

A. Polyester Fleece 

It is a 3-in-1 type of fabric that serves all purposes. These fabrics tend to stay much warmer, and damp and it dries faster. It tends to breathe as well as when necessary.

You can also try out wearing wind fleece with a well which includes an inner wind-blocking membrane.

B. Down-Insulated Jackets

This is another fabric that you should consider. It is very highly compressible for easy packing and offers more warmth for its weight than any other insulating material. 

The efficiency of down is measured in fill power from 450 to 900, since down is always inside a shell material, down jackets also offer some water and wind resistance. The drawback to down is that it loses insulating efficiency when damp.

C. Synthetic Insulated Jackets

They are the most popular option for rainy conditions because they retain insulating ability when they get damp. The fabric material offers added water and wind resistance.

C. Outer Layer

The outer layer protects you from wind, rain and snow. It is also known as the shell layer. It ranges from pricey mountaineering jackets to simple wind-resistant jackets which makes room for perspiration.

However, the outer shell is an important piece of fabric that helps during the stormy season as it allows wind and water to penetrate the inner layers.

Furthermore, they are classified into some categories which include:

A. Waterproof/Breathable Shells

This is the most expensive choice as this type of shell is good for a full-on condition. Generally, pricier equals drier, though higher-priced shells are often more durable as well.

B. Water-Resistant/Breathable Shells

These are more suited to drizzly, breezy conditions and high activity levels which makes them more affordable than waterproof or breathable shells.

In addition, they are typically made of tightly woven nylon or polyester fabrics that block light wind and light rain.

C. Softshells

This type of shell emphasizes breathability with its features of the type of soil, stretchy fabric or panels which will help to add more comfort.

Most feature stretch fabric or fabric panels for added comfort during aerobic activities. Many combine light rain and wind protection with light insulation, so they in effect combine two layers into a single jacket.

11 lights Best Essential Winter Clothing

In Chicago, there are some essential winter clothing that you must have. This clothing helps to keep your body warm and free from coldness from the present season. 

1. Sweaters

These are essential during the winter months. These sweaters consist of cardigan sweaters, pullover sweaters, turtleneck sweaters, and tunic-length sweaters. Whichever one you have can serve the main purpose as long as it is thick enough.

To get the suitable one for your winter, you should choose the ones that suit your style and also the ones that are thick enough to warm you up.

Invests in high-quality materials that will stand the test of time and for your sweater to last, it is important that you carefully study the instructions on its label.

2. Layering Shirts

Look out for layering shorts or long-sleeve tops. They will add some extra warming and care, especially during the winter or cold temperatures. It can offer comfort as well as other outfits.

3. Boots

This is another essential item that you must have for your winter. It will help to protect your legs from the cold while heating them from freezing. It also offers a lot of comfort and care. 

There are different styles to select from such as the knee-high and over-the-knee silhouettes which are a perfect fit for a night out. 

Combat styles lend a hint of urban grunge and also, Chelsea boots are a staple that’ll complete any daytime outfit. 

4. Denim

You can wear denim jeans all year long, but this winter essential is one you’ll wear repeatedly once winter arrives. 

A pair of skinny jeans pairs perfectly with booties or over-the-knee boots, and a wide-leg style with a fitted top lends a sense of understated coolness. Keep things timeless and try to avoid ripping or showy detailing.

5. Leggings

It is one of the most versatile winter clothing items to have on hand, leggings can be styled in many ways. 

Pair them with sneakers and a hoodie for a street-style vibe or try them with booties and a tunic sweater to keep it chic. The latter option looks especially great with faux-leather leggings.

6. Sweatshirts

Along with leggings, sweatshirts are a winter favourite that’ll earn their keep in your closet. Style them with leggings for simple, everyday winter outfits, or dress them up with booties and jewellery for a more fashionable look.

7. Socks & Tights

Every winter wardrobe needs a selection of socks and tights at the ready. Keep a variety on hand so you’re prepared for any fashion moment. 

However, we will recommend that you get tall socks to wear under boots, thick tights to pair with dresses, short socks for booties and patterned sheer tights for a playful touch.

Keeping these essentials on hand makes for a season that’s as stylish as it is comfortable.

8. Wool Coat

This is one of the favourite outerwear which usually extends below the knee, instantly adds an air of sophistication to any outfit and will forever remain in style. 

However, for easy pairing with the rest of your clothes, stick to neutral colors such as camel, black or navy.

9. Long blazer

For the winter, a blazer is one of these items. An excellent blazer is a wardrobe must that can be dressed up or down, depending on the season. 

A blazer might be the third item in your cosy outfit, draped over a sweater for a Sunday brunch with friends, or it might be the stylish jacket you need for your 9 to 5 job. You can build a style with a blazer you already own in your closet no matter what you’re going for.

10. Leather pants

Leather bottoms are currently very fashionable when it comes to wearing leather items. Low-waist and mid-waist pants are making a wild reappearance, turning some crazy heads whether they are brown, black, or even light colours. 

Additionally, it appears that many leather pants have a mid- or high-rise design, which is perfect for adding an extra layer of warmth when the weather is chilly.

11. Puffer Jacket

While a classic wool coat is undeniably chic, some moments call for a layer that’s a bit more casual. Cue the puffer jacket, a winter clothing essential that you can wear every day. 

A short puffer jacket is great for mild winters, and a long puffer coat will keep you toasty in colder climates.

Best Stylish Winter Accessories

There are many winter accessories to keep you warm and fashionable in the cold weather. These include

1. Scarves

A luxe scarf may seem like a trivial accessory, but it’ll create a winter fashion moment the second you toss it over your shoulders. Obviously, scarves also come in handy for staying warm even in the most frigid of temps. 

We suggest stocking your closet with several options, including a luxurious 100% cashmere scarf and an oversized wool scarf that doubles as a bold layering piece.

2. Beanie/Head Warmer

The term Head Warmer referred to the round-shaped ear cover used in windy areas to protect ears from cold air. It is an affordable headcover that is also called a woollen headband. 

It is usually manufactured using acrylic and woollen fabric. Kids and men usually prefer to carry woollen Head Warmer instead of wearing full caps. 

Keeping warm from head to toe means adding a hat or two to your winter capsule wardrobe. 

Furthermore, a beanie is one of our favourite styles for cold weather. Grab a few to accessorize different looks a cable-knit beanie is ideal for classic ensembles, while a pompom offers a more playful vibe. 

3. Winter Gloves

Classic winter gloves are thick and warm and offer protection from wind and cold. Some winter gloves have waterproof inserts for better protection from wet snow and water. 

Solid gloves are usually made of synthetic materials such as nylon, polyester (including fleece), polyurethane, neoprene, and spandex. Man-made materials are lightweight and durable and these characteristics make them suitable for producing dependable winter gloves

Winter gloves are used for protection in cold conditions and environments and are suitable for winter outdoor activities such as snow sports, going out, driving, bike riding, motorcycling, and backcountry adventures.

You can buy touch screen sensitive gloves (Yes, there are gloves designed to help the smartphone addiction) or you can get a variant which has flaps over the fingertips that you can pull back when you need to use your phone, keeping the rest of your hands toasty.

4. Poncho

Just like an oversized blanket scarf, Poncho is like an outer garment that is designed to keep the body warm. 

A simple Poncho has a single large sheet of fabric with an opening in the centre, for the head, and often it has an extra piece of fabric serving as a hood. For in-between weather, grab a poncho. It will add warmth (and some charm) to your outfit.

5. Earmuffs

This adorable stylish accessory is designed to cover a person’s ears for hearing protection or for warmth, hence making them perfect for winter. The cute furry earmuffs will keep your ear from freezing. As they are available in different prints, you can pick whatever you’d like!

Pick the earmuffs that are also headphones and that might just be the most genius winter accessory ever invented.

6. Mittens

Another cute accessory that is a must-have during winter is the mittens. There’s just something so delightful about mittens. They are hands down the best type of gloves for winter. 

Mittens are a type of glove with a single part for all the fingers and a separate part for the thumb. Although one major disadvantage of mittens is their dexterity, they do keep your hands warm and cosy during winter. 

These are great options for additional winter accessories for men and winter accessories for women which are colourful and comfy at the same time.

7. Headbands 

The headband is an essential tool for the winter season. Just get one that has been knit or knit one for yourself while in your spare time. Knitting it well will go a long way to help solve the problem of packing your hair as to avoid it from cutting off gradually. 

However, regardless of the season, this accessory is worn on the hair or around the forehead, usually to hold hair away from the face or eyes. 

During winter, they help you cover your ears while adding a style statement to your outfit.

8. Sunglasses And Goggles, Sunscreen

Sunscreen is essential for winter activities since the snow is very reflective of sunlight. They can be called sunglasses and goggles. It’s very important that your sunglasses have UV protection to prevent snow blindness. 

Goggles are for windy days when you need more protection.

Our Best Dressing For Special Winter Activities

1. Layer Clothing For Winter Workouts

The best way to stay warm and dry during cold-weather exercise is to learn how to properly layer your clothing. 

By knowing the layers, it will help you to know how to wear your clothes especially in a specific combination of layers, you will more easily regulate your body temperature, keep moisture away from your skin, and stay warm and dry even as you are working up a sweat.

A. The Base Layer

The base layer is in contact with your skin. A tight-fitting and wicking material is best to keep you warm and dry. Polypropylene, silk, polyester, Thermax, Thinsulate, and wool are all good choices.

Avoid cotton because it traps moisture, so it stays wet and draws heat from you. Base layers come in various weights (lightweight, midweight and heavyweight). Select a weight based on the outside temperature and your activity level. The lighter weight is better at wicking, the heavyweight has more insulation.

B. The Mid-Layer

The mid-layer provides insulation. It should be a bit looser than the base layer, but to function properly it needs to maintain contact with the base layer. Mid layers also carry moisture away from the base layer to the outer layer.

A common material for mid-layers includes down polyester, fleece, wool and newer synthetic/natural blends. Much mid-layer clothing has extras such as armpit zips, long front zippers, and adjustable cuffs and collars.

C. The Outer Layer

The outer layer blocks wind and allows moisture to escape. Typical outer layers include shells made of Gore-Tex or a similar material. Extras such as pit zips, ankle zippers (for pants), and a variety of ventilation options are standard.

Outer layers should also be tough enough to withstand tears and abrasions. Other less high-tech options may include wind-resistant materials or water-resistant fabrics.

To maintain the life of your clothing, follow the care instructions on the item. Synthetic, technical fabrics need to be cleaned properly in order to wick, insulate and repel water. Special cleaning products can restore moisture-wicking and water-repellent properties if necessary.

2. Winter Layer Clothing For Night Out & Date Night

Going on date night during the winter period can be challenging especially when you don’t know what outfit to wear that can serve both maintaining your body temperature and still looking sexy as you should.

However, there are many places where you can get where you can find but while doing, don’t forget to apply the principles of the best way to make knowing which outfits the outfit Here are some tips that can help you:

A. You can choose to wear a turtleneck sweater under a blazer or a coat. Or a dressYou can also wear a dress with tights and boots.

B. Add a touch of out for her number too A scarf, gloves, and a hat can keep you warm and add style to your outfit.

C. Choose fabrics that are warm and comfortable as much as wool, cashmere, or velvet.

D. Wear shoes that are comfortable and warm such as ankle boots or knee-high boots.

3. Winter Layer Clothing For Commuting To Work

Here are some tips for winter layer clothing for Commuters going to work:

A. They can wear a turtleneck sweater under a blazer or a coat. You can also wear a dress with tights and boots.

B. Using either a scarf, gloves or a hat can keep you warm and add style to your outfit.

C. Choose fabrics that are warm and comfortable such as wool, cashmere, or velvet.

D. Wear shoes that are comfortable and warm such as ankle boots or knee-high boots.

E. Wear a coat that is warm and long enough to cover your legs. You can also wear a puffer jacket or a parka.

F. If you’re wearing pants, make sure they’re wide enough to fit over your boots.

How Do You Dress For Outdoor & Indoor Activities?

To understand layering your clothing for outdoor activities, you need to know the function of each layer:

A. Base Layer (underwear layer): Wear thick outfits that can absorb the sweat off your skin.

B. The middle layer (insulating layer): Wear a cloth that can retain body heat and protect you from the cold.

C. The outer layer (shell layer): Wear a wool outfit that can shield you from wind and rain.


1. How Do People Dress In Chicago In Cold Weather?

If you are residing in Chicago, it is expected that while stepping out in the cold weather (winter), you must wear a warm coat or jacket, a pair of head warmers, gloves and a pair of boots. However, your attire depends totally on the occasion.

2. How Do People Dress In Chicago In January?

During the first month of every year January, the resident of Chicago wears winter clothes such as thick jackets, scarves, hats, gloves, and winter boots.

3. Is Chicago Cold During Christmas?

In December, the city of Chicago is on the colder side which is on an average high temperature of 37°F (3°C)

4. What Is The Snowiest Month in Chicago?

In the city of Chicago, the snowiest & coldest month is usually January.

5. What Month Is The Best For Visitation To Chicago?

The best months to visit the city of Chicago are April to May and September to October. As of that time, the temperatures are warm with a lot of festivals ongoing.


The major secret to knowing how to dress during the winter in Chicago is by properly understanding that it is not just about dressing or clothing, it is also about knowing that for each cloth, there are different layers which you must know.

However, if you have taken out your time to properly read through this article, then you must have gotten the heads-up on what you should do and what to look out for.

With the right clothing and complimenting accessories, you can enjoy all that Chicago has to offer throughout the winter periods.