Okay, let me walk you through how I ended up trying out that whole ‘old preppy’ thing recently. It wasn’t some grand plan, really. Just kinda happened.
Getting the Idea
So, I was scrolling around, you know how it is, looking at different styles. Honestly, a lot of the new stuff just feels… loud? Or maybe I’m just getting older, who knows. Anyway, I stumbled across some pictures, classic stuff, guys in button-down shirts, chinos, maybe a knit sweater. It looked comfy, simple, put-together without trying too hard. Reminded me of old college movies or something. I thought, “Huh, maybe I could try that.” Seemed like a nice change of pace from my usual jeans and t-shirts.
Digging Through My Closet
First thing I did was raid my own wardrobe. Saves money, right? I pulled out anything that seemed to fit the vibe.
- Found a couple of decent Oxford cloth button-down shirts, one blue, one white. Bit wrinkled, but solid.
- Had some khaki chinos that were okay, maybe a bit baggy by today’s standards, but passable.
- An old navy V-neck sweater my aunt gave me ages ago. Actually pretty good quality.
- My trusty brown leather loafers. Perfect.
So, I wasn’t starting completely from scratch, which was nice. But I definitely needed a few more pieces to make it work consistently.
Hunting for Pieces
Next step, I needed to fill the gaps. Didn’t want to spend a fortune. I hit up a couple of thrift stores first. You can find some real gems sometimes. Found a nice cable-knit sweater, cream-colored, for next to nothing. Score! Also grabbed another pair of chinos, a slightly darker shade, better fit this time.
I did end up buying one new thing – a Harrington jacket. Saw one online, looked classic, versatile. Decided to splurge a little on that because I figured I’d wear it a lot, not just for this specific look. It felt like a good staple piece.
Putting It All Together
Alright, now the fun part: actually wearing it. The first few attempts felt a bit…costume-y? Like I was playing dress-up. I put on the white oxford, the khaki chinos, the V-neck sweater. Looked in the mirror. It felt weirdly formal at first, even though it’s technically casual wear. I guess I just wasn’t used to tucking in my shirt all the time or wearing loafers instead of sneakers.
I tried different combinations. The blue shirt with the darker chinos and the cable-knit sweater felt better, more relaxed. Wore the Harrington jacket over a simple t-shirt and the khakis – that worked really well, felt more ‘me’. It took some fiddling to get combinations that felt natural and not like I was trying too hard.
Wearing It Out
So, I started wearing these outfits out and about. Just regular days, going to the store, meeting a friend for coffee. Nobody really pointed it out or anything, which was fine by me. It wasn’t about getting attention. The main thing I noticed was how I felt. Surprisingly comfortable, actually. The clothes were simple, non-restrictive. And yeah, I did feel a bit more put-together, even on a normal Tuesday. It’s like the clothes did the work for me.
Final Thoughts
So, will I be going full ‘old preppy’ every day? Probably not. I still love my comfy jeans. But, I really enjoyed the process. It was fun digging through old styles and seeing how they could work today. I definitely found some new outfit combinations I like and added a few solid, classic pieces to my rotation. It’s less about adopting a whole label and more about picking elements that feel good and look sharp in a low-key way. Yeah, I’ll definitely keep some of this in the mix. It’s easy, it’s comfy, and honestly, it just works.
