By Dan Morgridge

Put the board shorts down, son. There’s nothing more we can do for them. Flip the collar back down, pull the deep V-neck back up, and bid Sunshine City goodbye for now. Of course, we’re not in Sweater Vest Village yet. There’s a brief detour in Playa del Plaid! But seriously, let’s get you some weather appropriate clothes before the neighbors start to stare.

(Credit: Isle of Man’s facebook)

Isle of Man

3856 N Lincoln Ave
Chicago, IL 60613
(773) 697-8035
www.iomamerica.com

One of the hardest parts of dude fashion is accessories. Bracelets, necklaces, rings? Your average fella just can’t swing that swag. Your everyday gent has to get pretty ninja with their accoutrements. Maybe a nice aftershave? A killer bag? A hat or tie that doesn’t scream “I spent more money on this than I spent time learning how to hold a conversation” (difficult to find)? Isle of Man is a decent bet to help you find a couple tasteful bits of man-flair.

(Credit: shopriley.com)

Riley

1659 N. Damen Ave
Chicago, IL 60622
(773) 489-0101
www.shopriley.com

I know guys, there’s ladies stuff in here too. But don’t run away! The staff should be able to help you find something, and to talk to you in a manner that doesn’t inspire confusion, disgust, or serious worries about the financial priorities of the country. Also, their clothes look pretty good!

(Credit: haberdashmen.com)

Haberdash

607 N State St
Chicago, IL 60654
(312) 440-1300
www.haberdashmen.com

So we’re venturing into some haute hombre couture here, but think of it this way – one really good piece – a set of Sperry Top-Siders, a bespoke suit from their sister location…maybe even a hot shave? Because yes, yes they do do that.

(Credit: http://www.penelopeschicago.com)

Penelope’s

1913 W Division St
Chicago, IL 60622
(773) 395-2351
www.penelopeschicago.com

We’re not going to claim to be immune to the incredibly cute staff that Penelope’s has on hand. But we’re not going to say that having an attractive gal tell you that the shirt looks good on you isn’t the best assurance one could ever hope for while shopping. The gentleman’s selections are curated into a very small but very tasteful single wall, and tend towards the casual side. But what a man, what a man, what a mighty good-looking casual man (you’ll be)!

(Credit: belmontarmy.com / Google)

Belmont Army

855 W Belmont Ave
Chicago, IL 60657
(773) 549-1038
www.BelmontArmy.com

You could actually come out of Belmont Army dressed in any number of motifs. Maybe you want to vintage shop? Or perhaps you’re looking for an old canvas messenger bag that grandpa would have taken to war. Perhaps you’re a style maven who can run with the big labels featured on the main floor. Or maybe you’re so hip you can put a skateboard under those Nunn Bush loafers and skate right through the board meeting. It’s like a Choose Your Own Adventure of style (with just as many horrific possible combinations – choose wisely)!

Dan Morgridge unfortunately dresses like a jerk.