Emily V.
Yelp
I'm really not sure why I haven't reviewed The Outsider before now, seeing as I have been here dozens of times. But saying that should give you some idea of how much I enjoy this place.
The Outsider is a really solid spot for an evening out. It is located on the rooftop (9 floors) of the Kimpton Journeyman Hotel. You will have to enter the hotel to get here, but hotel staff are very used to directing people towards the elevators that lead to The Outsider. The space itself is wonderful - great views of the city, a variety of seating options, lots of comfy couches, and a large bar area. The Outsider is open year round. Even in the dead of winter, they manage to keep the majority of the bar open with the help of heating lamps.
The Outsider has an extensive drinks list. You will find your typical fare here - beers, wines, typical rail drinks, etc. But there is also a list of house-designed cocktails. These drinks are seasonal and are inventive and enjoyable, although quite pricey. In fact, I would say that The Outsider is generally one of the more expensive bars in the Milwaukee area. You are certainly paying for that rooftop view. For the cocktails, the price point feels fair, as these drinks are very nicely presented. But the price point is certainly quite high for the beers and wine.
A couple things to make note of:
-The Outsider on a weekend in the summer is going to be insanely busy. Come prepared
-People usually come dressed in nicer clothes. There is no dress code officially, but you won't see many people in sweats here.
-Service is a bit varied. Sometimes the servers will come to your seat to take your drink orders. Other times, you have to go up to the bar yourself. I think this is largely dependent upon their staffing and how busy the bar is on that day.