I recently took a weekend getaway trip to Boston with my bestie! I wanted to wear clothes that were cute but practical for the 20k+ steps we were going to be taking. I also needed to pack versatile clothes for a cold rainy day and a warm sunny day. I found the following inspirational pictures for cute and casual, yet stylish, outfits.
Day 1 - Light Layers
The first day of our trip was a rainy, active day on the Freedom Trail. I wanted to wear a pair of comfortable shoes and be able to layer. This is where I found a striped button-up shirt that was thin enough to layer with my rain jacket would be the center of my outfit.
The key elements I took from the outfit inspiration pics above are a button-up shirt, jeans, sneakers, and a fun pop of color. I also wanted to style the outfit with some chunky gold jewelry.
Here are the pieces I went with below:
- Blue and white striped button-down shirt – H&M Oversized Cotton Shirt
- Blue jeans – Abercrombie & Fitch Ultra High Rise 90s Straight Jean
- White sneakers – Cole Haan Grand Crosscourt Sneaker
- Green sweater – Hanes Men’s Ecosmart Fleece Sweatshirt, Cotton-blend Pullover, Crewneck Sweatshirt
- White bag/purse – (similar option to what I had) Reformation Mini Chiara Convertible Bag
The saving grace of this outfit was the Cole Haan sneakers. This is my second pair of these. My first ever trip to Boston, my first pair of these shoes got me through the trip plus many months afterward. The second pair of these are just as great!
Also wearing a lightweight button-down was the move as it got warmer after the rain let up and I could go without my rain jacket. In the evening, I added a green crewneck sweater for dinner and for the bars afterward. I didn’t need a sweater for the most part, but it served as a pop of color which made the overall outfit more interesting.
Day 2 - Colorful and Breezy
The second day of our weekend getaway was warm and sunny! I again looked for clothing to layer but had a bit more freedom that day. I was also looking to wear my new green sneakers and found the following outfit pictures as inspiration.
The key elements I was looking for this day and wanted to take from the photos were the casual wear of the colorful sneakers. The middle inspiration picture especially caught my interest as I had just made my linen tie top and thought that would fit the overall look and vibe.
Here’s a list of what I packed:
- Linen tie top – see my Linen Tie Top sewing post on how I made this top
- Blue jeans – Abercrombie & Fitch Ultra High Rise 90s Straight Jean
- Colorful sneaker – Gola Elan Sneakers
- Cotton sweater – (similar to what I have) L.L. Bean Women’s Cotton Ragg Sweater, Crewneck
This was the first day I wore the Gola Elan sneakers and they were comfortable, even after a whole day of walking the night before. Many reviews of these sneakers recommend sizing up, but I got my regular shoe size and they fit perfectly!
I was glad I packed a linen tank as it became warm as our day continued. Bringing a cotton sweater along was a smart move as well because the sweater added some more texture to the outfit and saved me when the wind picked up. I was also excited to find a silk bandana in a vintage shop that matched the pink on my shoes! I loved that this was a great functional, yet fashionable outfit.
Final Thoughts
Absolute staples for city exploring are sneakers and light layers that are easy to put on and take off. Comfort is key! I was also happy to spice up my capsule wardrobe with a new pair of sneakers and a sweater. I think these elements elevated these looks into something different and noticeable.
