Please leave your questions for Dear Cougar in the comment section below, or feel free to email me at cougar@leftcoastfashion.com

DEAR COUGAR: I’m heading to a wedding in Chicago this October. Can I wear a seersucker suit to the rehearsal dinner? – SEER-SUCKER IN NORTH CAROLINA

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Dear Seer-sucker,

Alas my friend I’m sorry, but no. I often joke that Chicago gets about 9 months of winter, which may not really be a joke at all. While us Californians can arguably stretch the usability of a summer seersucker suit (SSS) well into October with our lingering summer days, Chicago…not so much. The average temperature high in October for Windy City residents is, gasp, 60 degrees!

Now, the fact that you asked me if you could wear seersucker in the first place leads me to believe you want to make a statement. Two wintery wovens are perfect for making a statement and will keep you insulated as those temps drop to the 40s at night, Tweed and Houndstooth. eBay is the place to find jackets in either pattern that will be affordable, the rest of your ensemble might as well jump out of a J.Crew catalog.

This is how I would do it:

Paired to day with a great purple gingham J.Crew shirt, J.Crew slacks, a preppy as hell tie from Express and a purple paisley pocket square from around the LA Fashion District.

I hope that helps!

- Cougar