Lived in LA my entire life. Starting a project in Chicago through the winter.

Would love some recommendations for clothing or tips to navigate the winters there.

Congrats on the upgrade!! Chicago is such a great city. At least 8 times better than LA

1) You’re gonna be fine. I’ve lived in both and Chicago knows how to manage the cold.

2) Would suggest two coats - one for “cold”, like a wool topcoat (Uniqlo, BR, all the way up to the savile row tailors) and another less fashionable one for “waterproof apocalyptic cold” like a (Columbia with a reflective lining, north face heavy parka, Canada goose if that’s your thing)

3) For shoes, I tried rubber-sole dress shoes but didn’t like the way they compromised the sleekness of a formal outfit. I then tried SWIMs rubber shoe covers over my captoes before ultimately buying a pair of bean boots to wear until I got to the office, then changing upon arrival. Meermin, Allen Edmonds, and Alden all make shoes with a half-rubber sole that are office appropriate if you don’t want to schlep around two pair.

4) Don’t skimp on gloves, hat, scarf. You lose a lot of body heat through these areas and they’re a great way to show your style when coats can be so plain.

Me: USC grad, Manhattan beach native, Chicago resident for 7 years.

Swims overshoes, Sorel or LL Bean boots of you plan to leave at hotel (not needed youth), any thigh length (for a guy) or knee length (gal) down Columbia or North Face jacket (CGD is wayyy overkill), light gloves (HEAD runners for Costco), 180s for ears, and a scarf. It’s not THAT bad

For rubber soles, any shoe cobbler can add a thin rubber sole for like $10

Long underwear. You can save tons of $$$$ on all the other shit by buying a few sets of long underwear.

Not sure all the comments on long underwear. Have lived in Chi for 3+ years and I have one pair that I have worn maybe twice. Very rarely cold enough to need them. And I’m from Phx. Pants or jeans are generally sufficient unless it gets to like -10 or less.

Top of mind is I need a winter jacket - would like recs for professional looking ones - and rubber soles on my dress shoes to fight salt/snow.

I got a pair of Prada chukkas for my winter chi project. They were great!
Get a scarf, gloves, a wool pea coat, and some 180 ear muffs

LAYERS LAYERS LAYERS

Went to Chicago for MBA. You absolutely must wear long underwear—bottoms definitely, tops too unless your office is hot.
Sometimes I would even wear an underarmour compression layer, then a thermal layer, then real clothes

Banana republic has a great Black Friday sale going on right now (50% off) id start by browsing there!

Is your client in the city or burbs? Do you see yourself walking outside much? Depends a lot on that

Well. Good luck. Dress warm

Coat with a hood

If you are downtown, familiarize yourself with the pedway system - it’s great to be able to avoid being outside if you are anywhere near it. Boots worked out better for me but depending on how far you have to go outdoors, may be able to get away with rubber soles. I just kept my dress shoes in the office (client allowed us to store some things in a locked credenza when we weren’t there so i just let the shoes there all the time). Definitely love the head rubber gloves from Costco - if you go w a diff brand, just make sure they work with touch screen so you don’t have to take your gloves off.

Second the ped walkway system. If the client office is connect or close it’s great walking through there. Layers scarfs gloves and boots. Also shoe covers or wear tennis shoes even if boots aren’t needed. Once the snow starts they salt the sidewalks and the salt will eat away at your nice leather shoes

Thanks for the advice all. Client is not in the heart of the city, so won't be much walking around - I'm expecting door to door Uber or rental car. So with limited exposure it might not matter too much.

First thing I bought after moving to Chicago is a full length wind and water proof jacket. Theres a lands end outlet in Skokie if you want to save some money.

Just bought LL Bean 8" snow/rain boots and Sorel chukka boots. Will be targeting down jacket and gloves next