What a fun and enjoyable Cocktail Bar spot in the Pearl District in downtown Portland! My girlfriend mentioned this place and wanted us to do a date night here - it was an amazing experience to say the least! The vibe in here is so dope, as well. It feels like an upscale bar with the dim lighting and ambiance. The menu items, and drink names are super clever, too! We ordered the Belgium Waffle Espresso Martini and the Pickle Rick Martini - both were so good! I like pickle juice, but not like the biggest fan, and this Pickle Rick Martini was no doubt a perfect balance of vodka and pickle juice. I've really been into Martini's the last few months, and this was exceptional. The espresso martini was good and fun since it has that maple syrup taste vibe to it. For food, we got the Focaccia Bread and the Mr. Deed's Grilled Chicken Sandwiches with their, "ugly sauce" - WOW. It was all PHENOMENAL. The grilled chicken on our sandwich's were super moist and the cheese and their "ugly sauce" was fantastic (gotta know what's in this sauce so I can replicate it at home). The Focaccia Bread was legit a 11/10 (I wish I had a picture of it fro you all). They even give us a side of melted margarine for it (either that or butter, I couldn't tell). The bread was so fluffy, seasoned perfectly, and didn't even need the margarine with it! I even went up to the bartender before we left and said the bread was amazing. Personally, it's a great date night spot, but can legit be an any occasion spot for people looking for good drinks, burgers, chicken sandwiches, salads, bread, and experience! The hostess who sat us at our table and bartender's were super friendly. I really liked the concept of a nice dining experience with also going up to the bar to order everything - makes it easy for sure! I'll be going back here soon. Great job! read more

A silly operation not unlike its cousin at Silk Road. Price: outrageous across the board. Fare: decent burger and fries, unfathomably mediocre steak frites. Stingy cocktail pours. Ops: Despite seemingly plenty staff, no one answers the phone and you have to order at the bar (a predictable logjam). Dropped order items, inconsistent kitchen output for identical dishes, and a cocktail menu that apparently isn't updated with 86'd items ahead of a Friday night rush. Vibes: Dark, loud, zero atmosphere. I suppose they're aiming for a touch of class, which the experience and the menu betray. Try harder to elevate or don't try at all, but first focus on being a bar that can do the basics right. read more

Just tried this for the first time on a Friday night and was able to get a table for 3. The cocktails and food were great! I loved the menu but I'm a big Adam Sandler fan. The steak frites were my favorite followed by the bacon ... I normally wouldn't order a side of bacon as part of a meal outside of breakfast but let me tell you, this one is great! It's dark and moody, a great girls night or date night. read more

This is a great cocktail bar! We came in right at opening at got a table immediately. It felt a little odd to have to order at the bar at a place with an upscale vibe. The drinks were great, but the pours are small. A couple sips and they are gone. The burgers were a highlight for me. The beef was great quality and the toppings were all fresh. The bun was light, and still held up well to the juice from the burger. Well worth checking out! Good service, good food. read more

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We went to their sister bar Silk Road, but it was standing room only so we headed up the street to Pretty Ugly. Dark, romantic, great service, excellent cocktails, good vibes, music on point, and a full list of hamburgers there (though we just came from dinner and didn't get to try them; the fries were good though!).. The Seasonal Clover Club was floral and delicate. The Fugly Little Daiquiri was citrus forward and well balanced. The Banana Republic comes with colored sprinkles on top! All the cocktails were complex except the Lawn and Order was perhaps my least favorite only because it oddly tasted like the way my Kopari sunscreen lotion smells. However, that was just me and I'm sure it could be your favorite so don't steer away from it on my account. read more

Pretty Ugly - cocktail list - Cocktail Bars Near Me - Portland, Oregon

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Romantic and cozy vibes, great for a hangout and date night. Space is slightly limited so do plan ahead. Their drinks were punchy and strong which we really liked but for pretty steep prices. Didn't get to try food this time but seems like they mainly do burgers, again at pretty high prices. Overall, a fancy nice spot for a splurgy nightout. read more

Pretty Ugly - Cocktail Bars Near Me - Portland, Oregon

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One of my go-to bars in the Pearl area. The drinks here are consistently good and I have never had any issues. The people working here are friendly and quick to make our cocktails. I like their Ugly Old Fashioned and the Pretty Popcorn. They also can make any other drinks that you want, if the items on the menu isn't something you are feeling. read more

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Walked in said hello to the hostesses with a smile and was immediately asked "do you have a reservation?" What happened to greeting customers and faking a smile? That question with the nasty tone it was said in ruined everything for me. I was exhausted or else I'd definitely have put her in her place lol. To the owner, learn good customer service and teach it to your weird mean girl hostesses. read more

First time stopping in. We just got drinks before our dinner rsvp across the street. We were told they just opened Jan 2026! The bartenders were engaging and impressive, the cocktail selections were great and the menu of food looked amazing (locally sourced ingredients, elevated burgers, salads, sides). The dim lit lighting is warm and a great cozy vibe for date night. Can't wait to return! Sister bar to Silk Road right across the street! read more

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This speakeasy style cocktail bar has the cutest atmosphere, and their cocktail menu is inspired by movies, which makes ordering drinks extra fun! We actually went here after a long day at work - there were eight of us and they were able to accommodate us last minute! The drinks are not only creative but also absolutely beautiful. And don't sleep on the food - the burgers and fries are seriously some of the best bar bites in Portland. Great cocktail bar for a date night spot! read more

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Definitely recommend booking a reservation for the weekends. We went on a Friday and only had to wait about 10 mins for a table but it was completely full. The hostess was kind & sat us quickly. We had to order at the busy bar (they'll bring the food to your table) We ordered the Focaccia 8/10. Maple waffle espresso martini & the Mexico mezcal drink 10/10. Very loud so if you're looking for a quiet place this is not it. The place is small like most bars in the area so gets filled quickly. Would return again. read more

Stopped in before an art show around 5:30 on a Thursday and it wasn't too busy but steadily got busier. We sat at the bar and got very attentive service. The cocktails were delicious and strong. The salad and fries were good for sharing and the fried chicken sandwich was flavorful without being too saucy. I would definitely return with friends or for a date night. Classy but foofy. Nice people! read more

Pretty Ugly - Cocktail Bars Near Me - Portland, Oregon

100/10! Service was great - we got seated quickly during the Friday dinner hour without a reservation. Gorgeous, moody atmosphere with a stunning bar setup. Bartender was super friendly. The cocktail menu is amazing and I could barely decide which - we got two and loved both. And the food was phenomenal, top quality meat and sauces are homemade and delicious. Already planning to bring everyone I know here so I can make my way down the menu. read more

Pretty Ugly - Silly Rabbit and popcorn old fashioned - Cocktail Bars Near Me - Portland, Oregon

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I think the ambiance is amazing however the special cocktails were as tasty as they seemed to made out to be. It's a good burger but def better bars in Portland. read more

Pretty Ugly - Cocktail Bars Near Me - Portland, Oregon

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This place is pretty darn great!!! Love sitting at the bar with other friendly patrons. The service is excellent with several bar tenders and support staff serving up some great signature cocktails. Some of the best burgers in town!!! The ambiance is like a speakeasy. read more

Really liked the atmosphere here - lots of creative cocktails, and the food is better than you'd expect. Drinks were spot on, and the place just feels good. An easy pick if you want a laid-back night. read more

Got the chicken sandwich which I expected to have chicken breast but instead it was a thigh which I don't eat. The breading was thin and the pickles very sparse. Wish the menu warned me so I didn't wast food, also no side included. They use huge ice cubes to make smaller drinks and charge $18 for them. The steak frites had a very small strip for how much they charge. They called the drinks fruit forward but no cherries or garnish in the drinks? Also there were too many bar stools at the bar making it too crowded. Needed one or two less so there was elbow room. The espresso martini was really good tho read more

This is a new sister bar to Silk Road. First of all, let's start with the positives: - the ambiance is really nice here. The bar is a beautiful marble with a nice display of all of their liquors. - the staff is very pleasant, although I wasn't thrilled about the ordering at the bar experience for how high end this bar is, they were pleasant about placing orders. - the cocktails were interesting and different than others I've seen around town. Now the cons.... - the prices of the drinks were high, which is acceptable for an upscale establishment, but for the amount of liquor you get, it's insane. I'm talking $20 a drink (minimum) and they use the long ice cubes in your drink to make it look more "full". On top of that, their pours of liquor are TINY. I mean it felt like I was drinking half of a shot for an old fashion. So the value really isn't there at all for this place. - the food is also insanely expensive. $20 for a mediocre burger that DOESNT include fries. You have to pay $6 more for fries. Now if the food was 5 stars, I wouldn't have a problem with this, but the burger was the same quality as Red Robin, so the prices were wild. - for how upscale the bar was, the food menu is VERY casual. A bunch of fried food, and a long list of burgers. Now if that is their "theme" then that's fine, but they need to adjust their prices to be adjusted for the quality they are putting out. Overall, I won't be returning, that being said, I really love Silk Road. I just have to say this "concept" is a miss for me. either lower prices, or up level the food you are serving and make your pours for liquor normal, or lower those prices as well. read more

It's a beautiful bar with lovely staff. We sat at the bar and the bartender was really friendly and helped us with menu suggestions. The drinks were great, we ordered the espresso martini and a negroni. Best negroni ever. The steak frites were very good, but came out much rarer than I had asked for. The burger with brisket was very good, dessert was the highlight! The soft serve was phenomenal. Can't wait to come back and try more items. read more

Would love to leave a better review for this place but vibe was off. The staff were very friendly and helpful but holy f*ck the bathrooms were disgusting. I understand certain things but after ordering my drink and trying to use the restroom I had to leave immediately after.... Truly was that bad. Seriously awful. Ruined the whole experience. read more

I'm visiting Portland for a few days and a friend recommended checking out this bar. I'm so glad I did everything was amazing. The staff was welcoming, friendly and incredibly knowledgeable about the fine art of craft cocktails. They made great suggestions after taking the time to ask what I prefer. I had a burger that was the best I have had in a long time, including the delicious gluten free bun. It is a beautifully constructed space with a moody vibe and comfortable seating. I will definitely be visiting again on my next trip to the area! read more

Great burgers and cocktails. Nice, quiet place to grab a drink before the working people get out. Good date night spot.

Pretty Ugly is unique in its ordering style, meaning that you place your order at the bar and your meal/drinks are brought to you. I met a friend there and we decided on burgers and fries. I picked the classic burger (requested well done) and it was delivered up in a timely fashion. Chef Jazz brought our food to the table herself. I'm writing this review because it was the best burger I've had in the Pearl district! The staff was friendly and accommodating and Chef Jazz truly delivered. Definitely on my "go back to" list! read more

got told our wait was 45 minutes, they texted us 4 minutes later and then didn't hold our table lol. so we never go to even go. shitty experience but it's probably overhyped anyway! these places always are read more