My Argyle Sweater Vest Experiment
Alright, so today I was staring at that argyle sweater vest hanging in my closet again. You know the one – the navy blue with those kinda fancy grey and white diamond patterns? It’s been sitting there for weeks, maybe months even. Felt kinda guilty. Bought it thinking it looked smart, then totally chickened out on wearing it. Looked too… I dunno, like I was trying too hard maybe? Kept thinking about those preppy guys and got cold feet.

But I decided, enough is enough. Paid good money for it! So, the mission was clear: figure out how to actually wear this thing without feeling like a complete plank. Needed something simple, classic. Obviously, khakis popped into my head first. Everyone always says “chinos” or “khakis” with these vests. I had a pair – light tan, basic relaxed fit. Pulled them out. Step one done.
The Shirt Struggle Was Real
Now came the tricky part: what shirt goes under this thing? My first stupid mistake: tried a busy patterned button-down. Holy mismatch! The argyle was fighting with the shirt like two kids arguing over the last cookie. Looked terrible. Instant regret.
So, I switched tactics. Plain shirt only. Had a few options:
- Light blue Oxford: Safe bet. Slightly textured, kinda casual but neat.
- Crisp white tee: Super casual. Wasn’t sure if it looked lazy or just relaxed.
- Grey fine-knit long sleeve: Felt like this might be too matchy-matchy with the vest’s grey diamonds.
Tried them all on. The Oxford definitely looked the most “dressed”, kinda like what you see in old pictures. White tee? Actually didn’t hate it for a super chill vibe. The grey knit… well, it wasn’t awful, but kinda blended too much. Decision: Went with the light blue Oxford for this first try. Felt like the right balance of smart-ish but not stuffy.
Shoved my arms into the vest over the shirt. Buttoned it up – kept only the top button open. Felt important? Read somewhere that helps it not look too uptight. Maybe nonsense, but did it anyway.

Finishing Touches and Doubts
Stood in front of the mirror. Not terrible. Vest fit okay over the shirt. Khakis sat right at the waist like they should. Needed something on my feet. Sneakers felt too young, dress shoes felt like overkill.
Dug around. Found my brown leather boots – decent shape, not too rugged, not too fancy. Tossed them on. Actually… okay! The brown tied in with the tan khakis and didn’t clash with the navy vest. That worked.
Fiddled around:
- Tried tucking the shirt in? Looked clean.
- Untucked it? More relaxed.
Decided tucked was smarter for the Oxford. Maybe untuck later with the tee.
Walked around the house a bit. Did it feel weird? A little, yeah. Like I was playing dress-up at first. But also kinda… put together? I mean, compared to my usual hoodie, it definitely looked like I made an effort.

Verdict
Okay, so it’s doable! The key seems super simple: plain shirt underneath (stick to solid colors!), classic tan khakis, and shoes that aren’t too sporty or too formal. Brown leather is your friend. Don’t make the vest fight with anything else – it wants to be the star. Felt less nervous after wearing it for an hour inside. Maybe I’ll brave stepping outside tomorrow? Baby steps. If I can pull this off, seriously, anyone can. Looks way more complicated than it actually is to wear the dang thing.