Reader Questions: Boat Shoes + Socks?

Reader:

I was wondering how you felt about wearing some sort of graphic socks with boat shoes. I know it's a stretch, but I do wear straight slim or skinny jeans (that aren't too tight) so a little bit of my foot shows.

SB:

You know how some car commercials have a caption that says something like "Proffessional driver on a closed course. Do not attempt". Well, this is kinda like that.

Normally, socks with boat shoes - hell no. But, like I always say, rules are meant to be broken, and the most stylish people break them regularly. I do have a couple guidelines that could help you succeed:

- Never with shorts
- Not in the middle of winter (even with socks, boat shoes are three-season)

- Keep your pant leg opening slim. Like 7.5" across slim.

- Keep your inseam short. Like hardly touching the back of your shoe, hemmed at an angle so the front hits even higher, short. (or roll your pants/jeans)

- Wear striped socks, not argyle, check, or polka dot

- Wear the thicker, ribbed socks 

- Keep the majority of the stripes muted, and consistent with the tone of your pants. Maybe one thin colorful stripe, but you don't want them to be too loud.

 For Example, look for something like this:

Socks by Smart Turnout

Here is a rare picture of this look very well executed:

Photo by GQ

Thanks for reading,

SB