Hey Sid!
Age-appropriate blue jeans?
"A friend of mine who is a sharp dresser recently told me he disposed of his blue jeans as they were no longer 'age...
Liner Notes | Hey Sid!
You ask, Sid answers.
Hey Sid!
Winter Olympics in Milano/Cortina
“Hey Sid! I’ll be attending the Winter Olympics in Milan in February to cheer on team USA. I want to make sure I’m dressed...
Hey Sid!
Sid's Christmas List
"Hey Sid! What's on your Christmas list for 2025?" - Taylor
Hey Sid!
Rome in the rain
“I'm travelling to Rome this December on a church history study trip. The days are going to involve a looot of walking and I...
Hey Sid!
High School Reunion
“I have my 20-year high school reunion in November. What should I wear that gives off a sprezzatura vibe?” - David S.
Hey Sid!
"Fall Festive" & the emergency tie
“I have a wedding in Portland, ME at the end of the month with a 'Fall Festive' dress code, described as 'cocktail – jacket,...
Hey Sid!
Dueling Polos
“I wear a polo almost every day (I live in the Southeast and work from home) and have recently gotten into your Court style,...
Hey Sid!
The Carry-on Only (Italy Edition)
“Can I really do a week-plus business trip with only a carry-on suitcase (without resorting to hotel laundry or buying a new wardrobe)?” -...
Hey Sid!
The Do-It-All Dress Trousers
“I love suits almost as much as you, but lately I’ve been more interested in sport coats and blazers. My question is about the...