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WHAT TO WEAR: Winter

Chicago winters are notoriously brutal. There’s no way to completely protect yourself from the frigid temperatures, but throwing on as many layers as possible usually does a good job. Stylish layers, like this Fashionisto is wearing, take layering to another level–staying warm while also looking polished. This sweatshirt material roll-neck sweater and boots make this outfit casual. On the other hand, the gingham button-up shirt and coat give this outfit a touch of business-smart. That makes this outfit very adaptable. It can be worn to run errands and last all the way up to a nice dinner. It can easily be worn to lunch and still stay relevant for drinks with friends.

On top, the first layer that he has on is a gingham, red and blue, button-up Ralph Lauren shirt–similar to this one. This particular shirt is so versatile. It can be worn by itself in the spring or under a sweater like he is doing here, in the winter. It is casual but can make you look put together effortlessly. On top of that is a navy heather roll-neck sweatshirt with a front pocket from Banana Republic. This sweater is so great because the shape looks refined but the soft sweatshirt material and sweatshirt-like pocket on the front gives it a more casual feel. Another plus, it keeps you warm even in cold weather. This particular sweater is sold out, but I found a sweater that would go just as well and it can be found here. A classic peacoat is an absolute essential for every gentleman’s closet, especially if they live in an area with cold weather. This particular coat from Banana Republic is sold out but a similar, yet just as stylish, one can be found here.

On bottom, he is wearing these gray Levi Brand Jeans that can be dressed up or down. Levi Brand Jeans are so classic and will last you forever. To keep his feet warm he is wearing these stylish but practical boots from ALDO. Boots like these fare well for cold, snowy weather without sacrificing style. They are also lined with faux fur on the inside so they are sure to keep your feet nice and cozy.

On his wrist, he is wearing the Fossil Q Smartwatch with a dark brown leather band that can be found here. This watch doesn’t look like a typical smart watch, and I’m sure that just by looking at it you would never guess that it has so many other capabilities. It alerts you when you get a notification, using different colors for different apps or contacts and it can track your steps and activity, among other things. It is perfect for those that want the benefits of the new smart watch technology but also love the look of a classic wristwatch.

One Simple Change: Remove the sweater and coat and replace the boots with a nice pair of oxfords for an equally casual but refined outfit for spring.