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The Over-50 Guide to Styling a T-Shirt Like a Pro


Wondering how to dress up a t-shirt? It might seem like a basic piece, but when styled with intention, it’s anything but boring. Over the years, I’ve learned you don’t have to sacrifice comfort for polish. The secret lies in smart pairings, elevated accessories, and balancing casual with refined. In today’s post, I’m sharing six looks that prove a simple tee can take you everywhere—from errands to elegant brunches—with confidence and style.

Here’s What You’ll Find in This Post:

  • 6 polished t-shirt outfit formulas
  • How to mix basics with elevated pieces
  • Beth’s ✨Style Wisdom✨ for making tees feel timeless, not tired
  • Shopping links for each outfit
  • Answers to your t-shirt styling FAQs
  • Plus, see how T-Shirts play a big part in my Summer Outfit Formulas Video

Outfit 1: Patterned Tee + White Denim

A printed t-shirt adds just the right pop when paired with crisp white denim. I added a Raffia Belt for a summer touch and finished it off with neutral Suede Sandals and a coordinating hobo bag. It’s a laid-back look that still feels pulled together.

Outfit 2: Striped Tee + Linen Pants

There’s nothing more timeless than a striped bateau neck tee. Pair it with tapered linen trousers and sleek two-tone stud earrings for a breezy weekday lunch or afternoon outing. French-inspired but summer-ready.

✨Beth’s Style Wisdom✨

Outfit 3: Matching Short Suit + Tank

Matching separates are a chic way to wear a tee-like tank without looking too casual. This herringbone set from Banana Republic Factory adds subtle texture, and metallic fisherman sandals bring in just enough edge. I’d wear this for a dinner al fresco or a summer city stroll.

Frequently Asked Questions

Q: Can you wear a tee to dinner or an event?

A. Yes! Pair it with the right skirt, pants, and accessories, and it can easily go from day to night.

Q: What t-shirt styles are most flattering over 50?

A. Look for crewnecks or v-necks with a tailored fit—not too loose, not too clingy.

Q: How do you make sure a t-shirt doesn’t look too casual?

A. Elevate with texture, accessories, and polished pieces like trousers or structured skirts.

Outfit 4: White Tee + Tiered Maxi Skirt

This cotton poplin maxi skirt balances the ease of a vintage jersey tee. A slim black belt defines the waist while suede sandals and statement jewelry polish the look. It’s feminine and comfortable—perfect for museum days or garden parties.

✨Beth’s Style Wisdom✨

Love that beautiful Dôen Tiered Cotton Poplin Maxi Skirt, but don’t like the price tag? The Quince Organic Cotton Pintuck Maxi Skirt is a high-quality dupe that brings the same amount of chic, feminine charm.

Outfit 5: Ribbed Tee + Silky Wide-Leg Pants

For casual weekends, try this relaxed pairing of a striped long-sleeve tee and black gauze shorts. Simple black sandals and two-tone hoop earrings make it more intentional than your average t-shirt outfit.

Bonus Outfit: Long-Sleeved Tee + Wide-Leg Denim

I have been calling this outfit the Effortless Parisian. A striped boatneck tee is a timeless classic, and pairing it with wide-leg denim gives it a fresh, modern twist. I reached for comfortable ballet flats and added a raffia belt to define the waist and echo the natural textures of the season. A raffia tote or clutch pulls everything together for an effortless, casual-chic look—perfect for travel days, weekend markets, or just running errands with style.

YouTube

If you’ve ever struggled with what to wear during the summer, I’ve got you covered! In today’s video, I’m sharing 5 go-to outfit formulas I wear on repeat every season—these are the tried-and-true combinations that never let me down. From classic blazers and white button-down shirts to breezy linen pants and effortless dresses, these are the staples that define my signature style for Summer 2025.

YouTube video

More Summer Style Inspiration

Closing Thoughts

How to Dress Up a T-Shirt

T-shirts aren’t just for lounging anymore—they’re a wardrobe staple that can be styled for every occasion. From brunch to date night, the humble tee can keep pace with your summer plans. Which look was your favorite? Let me know in the comments, and I’ll see you tomorrow with more summer inspiration.

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  1. Sherry Ulrich

    I like your ideas on how to style a T shirt like a pro. Your outfits look so polished and put together. Not just a t shirt thrown over a pair of jeans or shorts and out the door. They usually end up looking sloppy and like something to clean the house in. These looks are so much more than that. Would not hesitate to wear them to the grocery store or to lunch with the girls.

Navy Coat winter outfit

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for women

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