I’ll admit that most days I take Lucy for a walk in an outfit more suited to function over form (thank you to whoever invented flannel lined jeans!). But, every once in a while I like to dress up for a little doggy date. Who better to hit the town with than my favorite girl? With the right destination in mind, yes, you can dress up to walk the dog!

Last month I got to take Lucy over to a dog friendly hotel that allows well behaved pups to hang out in the lobby, bar area and event space (they’re allowed to stay in the rooms too, but we live 5 minutes away!). Ace Hotels all over the country are pet friendly and I’ve heard from friends that they have taken their dogs to the Ace in their town. So, I was really excited to get a chance to dress up and take Lucy down to this hipster-chic hotel. If you want to check out the official pet policy it interestingly invites “stranger friends” if you want to think beyond dog!

The key to dressing up and taking your dog out on a date is where you go. Location, location, location! Obviously, don’t wear suede over the knee boots to the park. That’s not going to end well for anyone. And no matter what your destination is like, I recommend wearing a low or flat heel. Walking the dog in high heels, even if it’s just from the car to the bar, is dangerous for you and your dog.

My party and shopping tips apply to dog dates, too. Make sure your dog has already gotten a little exercise and allow them a potty break before you head inside. I always try to set Lucy up for success, and I hope you’ll take the same considerations with your dog.

For this date I put together a really fun outfit that’s still pretty practical because of the low heel on my boots. Speaking of these boots, they are one of my favorite pairs! Early 90s vintage Ombeline courtesy of my aunt. I slipped them over a pair of dark denim jeans and continued the 90’s vibe with a black cropped tank over a white blouse. I owe the white shirt to my fellow Style Social Pittsburgh bloggers Niki Whittle and Terra McBride, if you haven’t seen Niki’s 3 Ways to Wear series, check it out!

All photos by David Kindervater, taken on an iPhone.