Located in Blog, Gym & Fashion | Posted by Modern Gentlemen
January 19,2012

Surviving a Chicago Winter from the ground up.

Ask any Chicago resident what winter is like in our city and be prepared to suffer the consequences. Though we’ve had 50 degree days in November and January, most locals have something to complain about. The 3 inches of snow melted too fast and they had to wash their car twice this week after driving through slush, or the fierce winds of the windy city were too much for the Snooki weaves to bare (how many people know the real meaning behind the Windy City?). Well gentlemen, lucky for you I am here to give you 5 different options that will help you keep up with the trends and/or keep you warm this winter. We’ll start with the boot.


1) Red Wings


Here we have a classic Red Wing work boot. This photo was taken at Vivid Braille (2064 n damen ave Chicago, il) a boutique in Wicker Park owned by Prosper Bambo. Not only are these boots made to last but their traditional look will remain popular as long as the boot is around. Don’t be afraid to put some ware and tear into the leather, vintage is in! In fact, if you wanted a unique pair you can shop on Ebay for the original Irish Setters, a boot made by red Wing that you can no longer buy in stores.


2) Amongst Friends


Amongst Friends is a brilliant NYC based company that took the original army jump boot and added some style and comfort. These shoes are similar to the Red Wings in many way with a cost that is half the price. You can also purchase these boots in karmaloop and by using the Promo7 code ‘chip7’ and you will receive a discount.

3) RF x Sebago

This is a collaboration between my favorite shoe designer, Ronnie Fieg, and my favorite shoe, Sebago. I love the traditional Sebago shoe, made with quality leather and meant to last. Ronnie Fieg ahs been designing shoes for them with years and they get better each year. Here are the Dark Brown Senecas. I know most people are probably thinking that this is a fall boot, but with the crazy weather we’ve had this winter I always keep a pair of boots like this out of the box and ready to go. By far my favorite boot to wear year round.


4) All Saints

I don’t think Chicago was ready with this Gothic store was dropped right in the middle of Michigan Avenue. There are three things that every consumer should know before stepping inside:

1) they are trendy, what you see inside are fads currently trending in the UK

2) they are over priced, if that’s something you care about. If you don’t shop away!

3) they make great boots, regardless of whether or not you like the clothes their boots are magnificent.

This is their demise boot, it’s a military type boot not made for any other reason than to look good. If this boot isn’t for you they have plenty of other styles for you to choose from.


5) Sorel Caribou

I talked some friends into buying these last year before Winter hit and they’ve been thanking me ever since. This is an amazing looking boot that will keep for feet warm and dry all winter long. You can find Sorel boots all over the internet:




are a few sites that will definitely have them. Don’t forget to use the Promo7 code ‘chip7’ at Karmaloop for a discounted price!


These are 5 boots that should get any man through a winter in Chicago. Don’t be mistaken, no man can survive with just Sebagos or AllSaints boots alone, but you’d look good trying it. There are many different styles that I haven’t shown you with these brands. If you have any questions or comments please email me at moderngentlemanchicago@gmail.com and please check out our Facebook page Modern Gentlemen