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Dress Shirts Are Trending: What to Wear This Fall (2025)

September 19, 2025

Fall's biggest styling secret isn't another blazer or statement coat—it's the humble dress shirt having its main character moment. You've probably seen them everywhere: fashion editors pairing oversized button-downs with leather pants, influencers styling crisp white shirts with wide-leg trousers, TikTok creators making denim shirts look impossibly chic.

Samantha, our co-founder, used to make custom dress shirts for celebrity and pro-athlete clients, so seeing the dress shirt make this major comeback makes her so thrilled. There's something so satisfying about a well-cut shirt that just works—whether it's oversized and effortless or perfectly tailored to hug your curves.

The truth is, dress shirts are having a moment because they're incredibly versatile and comfy—but only when you choose the right cut, fabric, and styling for your unique proportions. That's where LookSky's virtual try-on becomes your styling advantage, showing you exactly how that oversized denim shirt or classic white button-down will look on your specific frame.

Quick Answers: Fall Dress Shirt Styling

How do I prevent dress shirt collars from splaying out? Look for shirts with properly fused collar bands and collars—this construction detail keeps collars crisp and structured instead of floppy. For collars that lay closer to your neck, try a cinch pin that adds both function and a polished accessory detail to your neckline.

How do you style dress shirts for fall 2025? Layer oversized dress shirts over fitted basics, tuck into high-waisted bottoms for waist definition, or wear open as a lightweight jacket over tank tops and jeans.

What fabric dress shirts are trending for fall? Crisp cotton for polished looks, relaxed linen for casual styling, and structured denim for that effortless cool-girl vibe.

How should dress shirts fit for optimal styling? Choose slightly oversized for layering, classic fit for tucking, or boyfriend-style for that borrowed-from-the-boys aesthetic.

Try LookSky's Virtual Try-On →

White Dress Shirt + Mini Skirt Formula

White dress shirt with mini skirt outfits

Dry Oversized Button Down in White

• Why it works: The oversized silhouette creates that effortless, borrowed-from-the-boys aesthetic while the crisp white cotton adds instant polish. The longer length is perfect for tucking, tying, or wearing open as a lightweight layer over fitted pieces.

Revolve Mara Shirt in White

• Why it works: The classic fit strikes the perfect balance between structured and relaxed, making it versatile for both professional and casual styling. The clean lines and quality cotton construction ensure it looks expensive and intentional rather than basic.

Alex Mill Jo Shirt in Cotton Poplin White

• Why it works: The poplin fabric provides just the right amount of structure while the tailored cut creates a polished silhouette. This is the kind of foundational white shirt that elevates every outfit while remaining comfortable for all-day wear.

Endless Rose Pu Slit Detail Skort in Taupe

• Why it works: It's still warm enough to warm skirts and dresses in Boston (but probably not for long). We love that the faux leather fabric adds edge and sophistication while the mini length shows off your legs. The subtle slit detail creates visual interest and the neutral taupe shade pairs beautifully with crisp white shirts for that high-low contrast.

Expert Style Tip: We love the way influencer, Jamie Loves, has a brilliant technique for wrapping shirts using a safety pin or brooch that creates instant waist definition—it's pure styling genius.

Ready to see how these pieces look on your frame? Try them on virtually in LookSky to find your perfect white shirt and skirt combination before you buy.

Striped Button-Down + Midi Satin Skirt

Striped shirts styled with wide leg trousers

Revolve Boyfriend Button Down in Bahia Breeze Stripe

• Why it works: The relaxed boyfriend fit and soft blue stripes create that effortless preppy aesthetic when worn open as a lightweight layer. The vertical stripes elongate your torso while the loose silhouette gives you that borrowed-from-the-boys charm that's both comfortable and chic.

Revolve Button Up Shirt in Stripe

• Why it works: The classic navy and white stripes are timeless and versatile, while the structured fit allows it to work both buttoned up or open as a cardigan. This is the kind of foundational striped shirt that anchors any preppy wardrobe and transitions seamlessly from casual to polished.

Bloomingdales Roux Balloon Shirt in Selene Stripe

• Why it works: The balloon sleeves add a modern twist to classic pinstripes while the oversized fit makes it perfect for layering over tanks. The subtle gray stripes feel sophisticated and work beautifully as an open jacket alternative to traditional blazers.

Reformation Cory Low Rise Slouchy Wide Leg Jeans in Sand Dollar

• Why it works: The neutral khaki tone is the perfect preppy complement to striped shirts, while the wide-leg silhouette creates that relaxed, lived-in elegance. The low-rise cut pairs beautifully with longer shirt layers without creating bulk at the waist.

Expert Style Tip: Mix it up with a pair of track pants, cropped tee and baseball cap for an updated take on the look. Perfect for grabbing coffee on those lazy Sunday mornings.

Ready to master this classic preppy layering look? Try these striped shirts and wide-leg pants combinations in LookSky to see which proportions work best for your frame.

Double-Denim

DL1961 Faye Oversized Denim Shirt in Del Ray

• Why it works: The oversized silhouette and medium wash create that effortless, lived-in aesthetic that's perfect for layering or wearing solo. The relaxed fit gives you that borrowed-from-the-boys charm while the classic blue denim serves as the perfect foundation for any double-denim styling.

Revolve 501 90s Jeans in Get On Board Selvedge

• Why it works: The straight-leg cut and vintage-inspired wash create clean lines that complement oversized denim tops beautifully. The high-rise fit defines your waist while the classic selvedge denim adds authentic texture and quality that elevates the entire look.

MaiTai Liada Oversized Denim Shirt in Washed Indigo Blue

• Why it works: The darker indigo wash adds depth and sophistication while the oversized fit creates dramatic proportions. This deeper denim tone works perfectly for creating contrast when styled with lighter wash bottoms or as a statement piece on its own.

Meshki Kirralee Straight Leg Cuffed Jeans in Indigo Blue

• Why it works: The straight-leg silhouette with cuffed hem creates a polished, tailored look while the rich indigo color adds sophistication to casual denim styling. The cuffed detail shows off your shoes and adds visual interest to the hemline.

Expert Style Tip: Contrast the top and bottom with denim washes for a 'just-threw-this-on' kind of vibe.

Ready to master the art of chic double-denim? Try these denim combinations in LookSky to see which washes and proportions create the most flattering contrast for your frame.

Why Personal AI Stylists Miss the Mark on Dress Shirts

Most AI stylist apps and personal styling services recommend dress shirts based on generic algorithms, not your specific body shape and lifestyle needs. Apps like Stitch Fix might send you trending pieces, but they can't show you how that oversized denim shirt will actually drape on your frame or whether that striped button-down will enhance or overwhelm your proportions before they ship.

LookSky shows you what works before you buy. No more guessing whether that "universally flattering" white shirt will actually flatter you.

Take the Style Quiz to find your perfect dress shirt →

Material Guide: Linen vs. Cotton vs. Denim

Linen Dress Shirts

• Why it works: Relaxed, lived-in texture adds casual sophistication to any outfit

• Expert styling tip: Embrace the wrinkles—linen is meant to look effortlessly rumpled, not perfectly pressed

• Best for: Weekend styling, vacation looks, and casual office environments

100% Cotton Dress Shirts

• Why it works: Crisp structure creates clean lines and polished silhouettes

• Expert styling tip: Look for poplin or broadcloth weaves for the sharpest finish, oxford for more casual styling

• Best for: Professional settings, layering, and when you want that "put-together" look

Denim Dress Shirts

• Why it works: Structured yet casual, bridges the gap between dressy and relaxed

• Expert styling tip: Mix denim weights and washes for sophisticated texture play

• Best for: Weekend styling, casual Fridays, and creating that effortless cool-girl aesthetic

A Note from Our Founder

"Before I started LookSky, I worked with celebrities, pro athletes, and shoppers to make them the best fitting custom dress shirts. This ethos, to deliver a deeply personalized experience extends to LookSky. LookSKy is your free personal AI stylist with a realistic virtual try-on that you can access 24/7 to find clothes that love your body without all the endless scrolling and outfit stress. We believe every body deserves to feel confident in their clothes." - Samantha Shih, Co-Founder of LookSky

Frequently Asked Questions

How do you style oversized dress shirts without looking overwhelmed? Balance oversized tops with fitted bottoms, tuck in the front for waist definition, or layer over fitted tanks. The key is creating contrast in proportions rather than wearing all oversized pieces.

What's the difference between AI stylist recommendations and virtual try-on? Other AI Stylists make recommendations based on general data or just your vibe, while LookSky extremely precise picks based upon your shape, style, color season, and more. Then, our realistic virtual try-on shows you exactly how specific cuts and fabrics will look on your unique body shape and skin tone.

Can dress shirts work for all body shapes? Absolutely, but the key is choosing the right cut and styling. Rectangle shapes benefit from tucked or tied styles that create waist definition, while pear shapes look great in structured cotton that balances their proportions.

How do you choose between linen, cotton, and denim dress shirts? Consider your lifestyle and styling goals: cotton for polished looks, linen for relaxed sophistication, and denim for that effortless cool factor. LookSky's virtual try-on can show you how each fabric drapes on your specific frame.

What's the best way to layer dress shirts for fall? Layer over fitted tank tops, under blazers, or open over loose pants. The key is mixing textures and proportions for visual interest while maintaining balance.