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...
Liner Notes | Hey Sid!
You ask, Sid answers.
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...
Hey Sid!
Sneaker Remix
“Hey Sid, been shopping with you for over a decade now. You and your guys have dialed in the ‘basic but elegant’ thing and...