Jack Sivan started his namesake tailoring and men’s wear business after freelancing for luxury labels like the Row.

How does one define men’s contemporary Minnesota fashion? You may not notice a distinctive regional style here until you take a trip out of state and return home to a sea of hoodies and Carhartt tan.

The last year has been tough on us — and our watches. With nowhere to go, we’ve had less need for our trusty timepieces, and have buckled them onto our wrists far less as a result. Instead, we’ve left ...