Men’s Fall/Winter Fashion

Men’s Fall/Winter Fashion

In order to be prepared for whatever Chicago weather throws your way, I recommend layering.  This applies to men and women alike; however, the topic at hand is focused on you fellas. I prefer to keep my recommendations classic but edgy, and with a few staple pieces you can develop a variety of looks with your current wardrobe. Feel free to reach out directly should you have any questions or need additional recommendations.

Boots - can make or break your outfit. (Tip: keep em’ clean - because whoever said, “those dirty shoes look great!”? Ah, no one - EVER.) Both brands below are made in the USA and can be dressed up or down depending on how you style them.



Helm Boots - Sam Original Dress Boot & Sam Black Dress Boot (can be purchased at Oliver & Rowan Chicago w/referral or online @




Oak Street Bootmakers Natural Trench Boot & Black Dianite Trench Boot (can be purchased at Independence Chicago or @


Vest, Waistcoat, Bodywarmer - whatever you prefer to call it - these are great staples to have and rotate in your wardrobe. Pair with your favorite button-up for work or with a thermal/henley and some jeans (J Brand, Joe’s, and AG all make classic denim with clean pockets and a variety of fits/washes that won’t break the bank) on the weekend.





Moncler Quilted Puffer (comes in burgundy and green) because a pop of timeless color is always an easy way to stand out in the crowd


Crescent Down Works Italian Vest in Navy (can be purchased at Independence Chicago)





Suitsupply Navy Waistcoat & Suitsupply Light Grey Bodywarmer in Pure Wool (both found online or in your local Suitsupply store)



Sweaters - are a wardrobe staple and can often be used through multiple seasons depending on weight. Sweaters vary greatly in price and fabric is often the differentiator. Quality fabrics will not pill if properly cared for so keep that in mind when making your purchase. Gant has been around for ages and I love their Boutique on Damen Ave. The following two sweaters are made by Gant and the second one comes in every color imaginable. It is also a lighter weight fabric which makes it great for fall with a t-shirt or easy to layer with a button up or in the winter.

Gant Cotton Block Structure Sweater




Gant Lightweight Cotton V Neck Sweater