Hi, moving to Chicago this fall to start at a T2 Consulting Firm. I was wondering what essential business attire I need to buy and any recommendations on where I should start looking. Also - where and what kind of pieces should I be looking at for winter business attire? Thanks!

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Really depends on your firm’s dress code/culture. Can you share more? Typically, Chicago is pretty relaxed when you go to an office.

Personally, big fan of Charles Tyrwhitt. Lots of choices, good prices, good quality. I’d start off there. They used to have a store in the loop, but not sure if it’s still around (but online works well).

And congrats on this new adventure, Chicago is beautiful during the winter time!!


Ditto Charles Tyrwhitt ^^

Get yourself a heavy winter coat - Patagonia, LL Bean, North Face, [Canada Goose if you have $$$ to drop] - warmer than you think you need, 🤣 [many people have 2 - the “it’s cold” and it’s “OMG how do people live like this cold” ]

Building off above - depends on attire in office, how often you’re at client, etc.


Are you male or female? That can help with brand recommendations.

As for attire I recommend:
Layers. Lots of layers all year. It may be 90 outside but you step inside at any business and its 55 w/ heavy AC.

Learn the pedway!! I avoid needing my mega winter boots to get to the office because I know the pedway and I can get from the train to my desk without going outside. I have to get TO the train but still.

Recommend some waterproof/resistant winter dress shoes, recommend plenty of nice sweaters and linen shirts for hot summers.

I love Uniqlo, Banana Republic, J. Crew and Anne Taylor/Loft as general work attire wear. If I go fancy, I go to Macy’s for PCAOB/Client attire.

Dress shoes, dress shirts, dress pants and/or nice chinos. Throw in some sweaters for winter and you are good.

You don’t really need anything past that in most offices anymore.

As mentioned above, Charles tyrwhitt is a great option for shirts. Pants will depend more on body type, but bonobos is a good option. For dress shoes, I would go with 2-3 pairs of Allen Edmonds - check their factory seconds to see if you can swing a deal.

You need good commuting boots. LL bean or sorrel. Not the biggest ones they make and not the shorties but the middle grade - above the ankle and warm and waterproof. A lot of people also have dress shoe covers. They are like rubber shows that slip over your dress shoes to protect from rain and the CTA.

Winter. As others have said, good warm, non-slip boots are essential. So is a really good warm coat. (Not a fan of Canadian goose as they’re a target for thieves and the logo is weirdly the same as bus and el drivers.Also overpriced.) Don’t worry what it looks like, by February no one cares. There’s winter and then there’s ugly winter as far as coats and footwear. Layers. Cashmere sweaters over shirts under coats. Extra socks and boots. Can’t stress the nonslip enough, it’s not the snow it’s the ice that will get you. As for the rest of the year, 85% of the time, bring a jacket. Cooler by the lake.

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