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What to Wear to Chicago, IL

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What to Wear to Chicago, IL

Chicago has a clear take on the four seasons, so knowing the weather before you visit is vital. Summer can be warm with high humidity or mild and slightly chilly, even during typically warmer months such as July and August. Temperatures are typically 10-15 degrees cooler along the lakefront year-round. Contrary to what people believe, the “Windy City” nickname stems from its politics, but the wind can be fierce particularly during the winter. Although it angers PETA members, you will always find a variety of furs worn during those frigid months. The penetrating chill can take down even a stoic Patagonia when temperatures can dip below zero during the day. And that, folks, it not considering the wind chill! Spring is notoriously wet from melting snow and ice, and rain is common. How does one dress to impress with all of these meteorological demands? Style in Chicago is slightly classic, conservative, and chic, regardless of day or night. There is plenty of it to keep Mother Nature in her place.


For winter: layering is key with cozy knits like Alpaca, which is one of the warmest knits available. Lined dress pants, thick tights, and skirts in heavier fabrics are staples for day or evening. A good, warm coat, scarf, and gloves are mandatory. Hats are common and even more so downtown where walking is prevalent. For daytime, look to jeans either with flats or tucked into boots. Many locals rely on ankle boots with pants and jeans, which add a bit more protection from the elements. For evening, sweater dresses are an easy way to keep toasty without compromising style, though a good, warm evening coat can open up dress options. The use of valets and outdoor heaters makes quick entrances to locales and cars easy and helps maintain style without looking like the abominable snowman.


Many women wear jeans out at night with pretty sweaters, heels, and tops. This is acceptable for most restaurants, clubs, etc., provided the outfit is polished and put together. For men, sweaters layered over dress shirts and trousers or jeans are common winter outfits. In terms of footwear, beware!  Chicago and its surrounding area use salt to melt ice and snow -- it can be extremely damaging to leather, suede, and other materials, so plan footwear accordingly.


For Spring and Summer: Spring temperatures can be very chilly in Chicago, so check the weather forecast and adhere to winter dressing guidelines. This season is infamously wet due to melting ice, snow, and rain, so be sure to bear in mind when planning footwear. Rain boots and rubber shoes are not uncommon, particularly in the city where walking is prevalent. Stores such as Neiman Marcus on Michigan Avenue always offer highly disguised weather repellant boots to avoid the alternatives.

Ah, finally. Chicago is summertime’s favorite city. Shorts and skirts are very popular, especially when worn with basic tees and tops and a variety of footwear. However, you’ll want to keep your flip flops at home. A great, easy casual dress with a strappy leather flat is a summer uniform for locals. Night and party attire can go glam with dresses and heels, but great jeans and a sexy top with heels is also customary. Again, because weather can vary even during summer months, layering is key year round. For men, summer attire is ultra casual.  Think shorts and jeans with tee shirts, etc. This is acceptable for day and night time, though avoid going too casual at more upscale restaurants and locales.


Shopping Tips: Michigan Avenue will satisfy just about any fashionista fix from a fan of H&M to one happier with high end designers like those found at stores such as Burberry, Ralph Lauren, and Escada. The Barney's New York is located slightly west of the Magnificent Mile, but is small and paltry. Skip it to take advantage of boutiques like Intermix and Jake on Oak and State Streets nearby.

Northern neighborhoods like Lincoln Park and the Belmont area are ripe with trendy, hip boutiques and super-stocked thrift stores. Downtown on State Street can be fun, but buyer beware – it’s mostly stores like Limited and the Gap which you’ll more than likely find online or at home.

And here is an insider’s tip: for one of a kind, custom pieces for all events including luncheons, weddings, and hot nights out, give Mira Couture a call. Located on Delaware Street, Mira (a former professional ballroom dancing champion) and her team can create anything you have in mind, and they host the needs of celebrity clientele who often come through town. No name dropping there, though!

Comments ( Add a Comment )

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By Paige Rolfe


Yes, they are a little strange fitting in that region! Had some potential, however. A nice black dress slack or pair of skinnies might be better alternatives for a Chicago trip!

Posted:
953 days ago
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By Mandy


I went to Chicago in February for fun, yes i know it is freaking cold that time of year and who wants to visit Chicago when they can go some where tropical. me that's who :) best thing to do is LAYER it was snowing outside and cold as he** but in the club it was HOT (good thing they have coat check). attched are two photos of the same night!

Posted:
957 days ago
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By sticks


I DO NOT like those "horseback riding" leggings in the pic above, they make her vadge look strange. People in Chi town DO NOT need to rock the camel toe.

Posted:
957 days ago

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