September 24, 2026 Fresh Ways to Wear a Classic Polo
A striped polo can make even your worn-in jeans look like part of a plan. Maybe it’s the collar, maybe it’s the rhythm of the stripes, or maybe it’s that little nod to the tennis court. Either way, this shirt deserves to work its way into your fall wardrobe. Here are just a few ways.
1. Keep it Loose
Start with loose denim. A roomy polo tucked into baggy jeans creates a nice balance between neat and slouchy. Add a leather belt and ankle boots to lock in the look. Bonus points for layering in an oversized bomber jacket.
2. Highlight a Color
If your shirt has bold, colorful stripes, let one of those colors lead the rest of the outfit. A red stripe might call for red socks peeking above loafers. A butter-yellow stripe could pick up a cardigan draped over your shoulders. You do not need an exact match; a small echo is enough to make the color feel connected.
3. Mix with Flannels
Flannel and fall go hand in hand, so don’t be afraid to bring your striped polo into the look for a bit of mixed patterns. Layer it under an open flannel shirt or simply tie the flannel shirt at the waist.
4. Pair with a Skirt
Want to take the shirt somewhere less expected? Pair it with a slip skirt or a full cotton midi skirt. The sporty top keeps the skirt from feeling too precious, while adding a retro feel to the overall look.
When shopping secondhand, look beyond your usual section. A men’s polo might give you the relaxed shape you want, while a fitted knit version can tuck neatly into trousers. Make sure to try it on: the way the shoulders sit can change the look.
However you wear it, a striped polo brings character to fall pieces you already own. Find one that catches your eye at your local Crossroads, then see where the stripes take you.
