Last weekend, we went to Chicago for a friend’s birthday and decided to make a weekend trip out of it. Weekend trips are always a good idea until it’s time to pack for them. I always end up bringing enough clothes to dress a village, and then quickly regret it when I get home and have to unpack everything. We didn’t have specific plans outside of visiting a friend for her birthday, so I decided to put together a few outfits for a nice dinner, a day of exploring (by exploring.. I mean shopping)!
The first look I packed is more on the casual side, so I decided to wear this while we walked around the city and did a bit of shopping. This cream paisley top is simple but has the cutest ruched detail around the waistline and a relaxed balloon sleeve. I love that it’s lightweight and is the perfect transition top to layer under a leather jacket or trench coat. I paired it with my favorite denim flare jeans that unfortunately just sold out. I linked a few others below that don’t have the button detail down the leg but are the same style, fit, and wash. I’m keeping my fingers crossed they restock the exact ones I wore soon! I paired my staple ankle boots with this look because they are the perfect height for my flare jeans and they’re a comfortable heel to walk around in. This simple outfit is one that is perfect for a casual fall brunch or dinner with the family.
My date night look is a combo of a few timeless pieces and trendy accessories that I think every woman needs in her closet. I had been on the hunt for the perfect nude blazer and found this cream blazer, which has been my most worn item in my closet the last few months. I love this blazer because it frames the body so nicely. It takes a bit of searching to find a blazer that is oversized but doesn’t take away from your shape, but this one checked all the boxes for me. Under the blazer, I had a little cutout moment with my black long sleeve cutout top. Again, this is another great basic that you can dress up or down. I love having an all black moment and pairing it with my Revolve malta leather pants. I had to have a moment of silence for these leather pants when they came in the mail, they are amazing!! They look great dressed down with a sweater and sneakers but for this look I paired them with my classic black pumps. As for the accessories, I wanted to go bold with my oversized hoop belt (which I also just ordered in black because I’m obsessed) and my chunky gold necklace. My favorite thing about this outfit is that its such a nice balance of staples and statement pieces.
The last look I packed was for my friend’s birthday party! With temperatures being a bit cooler in Chicago, I knew I wanted to wear something that would keep me cozy throughout the night. My cream sweater dress was the perfect look for the evening. This sweater dress is a nice neutral color and the style is flattering around the waist. I like that the material is thick enough to keep you warm but thin enough to layer under a blazer or winter coat. I completed the look with my white blazer (similar linked) and my Bared Footwear knee high suede boots. I’ve shared these boots on my social media and they seem to be everyone’s favorite! They really are the only brand I’ve found that makes high quality heels and boots you can comfortably walk around in throughout the day. These boots are currently sold out but I know they are planning on restocking soon, so I will be on the look out and let you know when they’re back in! I’m going to sound like a drama queen when I say this, but having my outfits planned out instead of overpacking was such a game changer and made the “get ready” process less stressful. I hope you love these looks and can use them as inpso for your next little weekend getaway!