Blog: Crossroads Style

August 5, 2025 Crisp Style: Tailored Shirts

As we move into fall, our wardrobes begin to shift from breezy summer staples to pieces with more structure and polish. One option that works beautifully for this is a crisp tailored shirt.

Versatility Defined

For workdays, pair one with high-waisted trousers and loafers for a smart, professional look. On weekends, leave it untucked over straight-leg denim and add sneakers for a relaxed yet elevated vibe. Tailored shirts strike that perfect balance between casual and formal, making them an ideal foundation for countless fall outfits.

woman wearing a white tailored shirt with black tie and black trousers

man wearing a white tailored shirt with khakis and trainers

One of the best things about tailored shirts is their adaptability across styles and settings. Layer one under a cozy crewneck sweater with just the collar peeking out, or wear it open over a fitted turtleneck for a more fashion-forward take. They also transition seamlessly from day to night when you swap your flats for ankle boots or heels and add a statement accessory.

woman wearing a tailored shirt under a long black vest with mini skirt

Comfort + Polish

A tailored shirt in soft flannel or brushed cotton brings both comfort and polish to everyday wear.  A slightly oversized cut worn with a belt at the waist creates a modern silhouette while maintaining that classic structure. Whether you prefer a crisp white version, a subtle stripe, or a rich seasonal tone like burgundy or olive, there’s a style to match your fall mood.

man wearing a blue button-down shirt with brown trousers and loafers

This season, think of tailored shirts as your go-to layering hero. They provide a clean, sharp base that lets you mix textures like leather jackets, chunky knits, and tailored wool coats, without the look feeling cluttered. And because they’re timeless, they’ll remain a wardrobe favorite well beyond this fall.

person wearing a button-down shirt under a jacket with scarf tie

As you update your closet for the cooler months, consider investing in a few tailored shirts. They’re a smart choice that will keep you stylish, no matter where the season takes you.

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