Okay, here’s my take on dressing for 55-degree weather, based on my own trials and errors!

Alright, so 55 degrees, right? It’s that weird in-between weather where you’re not quite freezing, but definitely not rocking shorts and a tee. I always struggle with this! So, I decided to actually track what I wore and how comfortable (or uncomfortable) I was for a whole week when the temps were consistently around 55. Here’s what I learned:
Day 1: The T-shirt and Light Jacket Fail
- Started with a regular cotton t-shirt and a thin, unlined windbreaker.
- Mistake! Felt fine in the sun, but as soon as a cloud came over, I was chilly. And at night? Forget about it. Shivering city.
- Learned: A single layer ain’t gonna cut it.
Day 2: The Overdressed Disaster
- Went the opposite direction. Long-sleeved thermal shirt, a fleece, and a heavier jacket.
- Big mistake, HUGE! Overheated like crazy by midday, especially walking around. Ended up carrying the jacket and fleece.
- Learned: Need something I can easily take off and put back on.
Day 3: Layering is Key! (But Do It Right)
- Okay, I get it, layers. But this time, I tried a light, breathable base layer (a thin merino wool tee), a flannel shirt, and a light trench coat.
- Much better! The merino kept me from getting sweaty, the flannel added warmth, and the trench was perfect for blocking the wind. Could easily adjust by unbuttoning the flannel or taking off the trench.
- Learned: Breathable base layer + adaptable mid-layer + windproof outer layer = gold.
Day 4: The Denim Experiment

- Wore a long-sleeved cotton shirt, a denim jacket, and jeans.
- Pretty good! Denim blocks the wind nicely. Still a little cold when the sun dipped, but overall, not bad.
- Learned: Denim is a decent option if you don’t have a trench coat.
Day 5: Activewear Adventure
- Tried a long-sleeved athletic shirt, a lightweight packable down jacket, and leggings (I was going for a walk).
- Super comfortable for being active! The athletic shirt wicked away sweat, and the down jacket was surprisingly warm without being bulky.
- Learned: Activewear layers are great for 55 degrees, especially if you’re actually being active.
Day 6: The Sweater Success
- Wore a cotton sweater over a t-shirt with a light jacket.
- Okay, this was pretty comfy. The sweater provided a good amount of warmth, and the jacket was there if I needed it.
- Learned: Sometimes, a simple sweater is all you need.
Day 7: The Final Verdict (My Go-To Outfit)
- I settled on a thin merino wool base layer, a flannel shirt (buttoned or unbuttoned depending on how I felt), a light trench coat or denim jacket, and jeans or chinos.
- This combo was the most versatile and comfortable for me. I could easily adjust it to the changing weather conditions.
Key Takeaways for 55 Degree Weather:
- Layers, Layers, Layers: Seriously, that’s the key.
- Breathable Base Layer: Merino wool or synthetic fabrics that wick away sweat are your best friends.
- Adaptable Mid-Layer: Flannel shirts, sweaters, or light fleeces that you can easily take off or put on.
- Windproof Outer Layer: A trench coat, denim jacket, or windbreaker to block the wind.
- Consider Your Activity Level: If you’re going to be active, opt for athletic wear. If you’re just hanging out, a sweater and jacket might be enough.
Hope this helps! It’s all about experimenting and finding what works best for you. Good luck dressing for that in-between weather!