From layering rules to tucking etiquette, dress shirt vs button-down differences to when you can get away with a polo — this is the complete guide to wearing shirts the right way in every situation.
If minimalist basics are your foundation, our brands like Everlane guide maps that segment by price and ethics.
Polo instead of a dress shirt? We answer whether to button the top button.
Shirt Types Explained
| Shirt Type | Formality | Best With | Avoid With |
|---|---|---|---|
| Dress Shirt | Formal → Business | Suits, dress pants, ties | Casual shorts, sneakers |
| Button-Down (OCBD) | Smart Casual | Chinos, jeans, blazers | Very formal suits |
| Polo Shirt | Casual → Smart Casual | Chinos, shorts, jeans | Full suits |
| T-Shirt | Casual | Jeans, shorts, sneakers | Formal anything |
| Linen Shirt | Casual → Smart Casual | Shorts, chinos, sandals | Winter, formal events |
| Flannel | Casual | Jeans, boots, layers | Office, formal |
Layering Guides
- How To Wear A Cardigan Over A Collared Dress Shirt
- How To Wear Crew Neck Sweaters Over Dress Shirts (7 Tips)
- Do You Have To Wear A Shirt Under A Sweater?
- How To Wear A Flannel Shirt Over A T-Shirt (7 Tips)
- How To Wear A Hoodie Over A Collared Dress Shirt
- How To Wear A Polo Shirt With A Denim Jacket
- Can You Wear A Shirt Over A Sweatshirt? (Explained)
- How To Wear A Shirt Over A T-Shirt (7 Essential Tips)
- Do You Have To Wear A Shirt Under A Hoodie Or Not?
- Can You Wear A T-Shirt Over A Turtleneck?
- Can You Wear A T-Shirt Over A Button-Up Shirt?
- How To Wear A T-Shirt Over A Hoodie (6 Tips)
- How To Wear A T-Shirt Over A Long Sleeve (7 Tips)
- Do You Have To Wear A T-Shirt Under A Sweater?
- How To Wear A T-Shirt With A Denim Jacket
- Should You Wear An Undershirt With A Button-Down Shirt?
- Should You Wear An Undershirt With A Polo? (Solved)
- Do You Wear An Undershirt With A Tuxedo?
- How To Wear An Undershirt With A White Dress Shirt
Shirt Etiquette & Rules
- How To Wear A Black Shirt To A Funeral (The Right Way)
- Can You Wear A Black Shirt To An Interview?
- Can You Wear A Black Shirt To A Wedding? (Solved)
- Can Men Wear A White Shirt To A Wedding? (Solved)
- 8 Easy Fixes For Chest Hair Sticking Through Your Shirt
- 4 Ways To Wear Cufflinks With Any Buttoned Shirt
- Can You Put A Pocket Square In A Dress Shirt?
- Can You Wear A Polo Shirt To An Interview?
- How To Wear A Polo Shirt To A Wedding (Properly)
- Should You Tuck In A Polo Shirt? (Explained)
- Tucked Or Untucked Shirt For Business Casual?
- Should You Wear An Undershirt With A Button-Down Shirt?
- Should You Wear An Undershirt With A Polo? (Solved)
- Do You Wear An Undershirt With A Tuxedo?
- How To Wear An Undershirt With A White Dress Shirt
- How To Wear A White Shirt To A Funeral Respectfully
Shirt Types & Comparisons
- Aloha Shirt Vs Hawaiian Shirt Vs Cuban Shirt: Differences
- Can You Wear A Regular Dress Shirt With A Tuxedo?
- How To Wear A Cardigan Over A Collared Dress Shirt
- How To Wear Crew Neck Sweaters Over Dress Shirts (7 Tips)
- Crew Neck Vs Sweatshirt: What’s The Difference?
- Dress Shirt Vs Button-Down: Differences And How To Choose
- Golf Shirt Vs Polo Shirt: Differences And How To Choose
- How To Wear A Hoodie Over A Collared Dress Shirt
- How To Shrink A Dri-Fit Shirt In 4 Steps
- How To Shrink A Shirt In The Dryer (In 3 Steps)
- How To Shrink A Shirt Neck In 7 Steps
- Can You Put A Pocket Square In A Dress Shirt?
- Can You Wear A Polo Shirt To An Interview?
- How To Wear A Polo Shirt To A Wedding (Properly)
- How To Wear A Polo Shirt With A Denim Jacket
- Should You Tuck In A Polo Shirt? (Explained)
- Should You Wear An Undershirt With A Button-Down Shirt?
- Should You Wear An Undershirt With A Polo? (Solved)
- How To Wear An Undershirt With A White Dress Shirt
Frequently Asked Questions
Should you tuck in a shirt for business casual?
Yes, usually. If the shirt has a flat hem (straight across the bottom), it’s designed to be worn untucked. If it has a curved hem (longer in front and back), it’s designed to be tucked in. For business casual, err on the side of tucking — it looks cleaner and more professional.
Axel is the founder of ReadySleek and has spent over 5 years researching and testing men’s grooming products, skincare routines, and hair loss treatments. His work combines hands-on product testing with insights from dermatologists and trichologists to deliver evidence-based grooming advice.
He specializes in men’s skincare (including ingredient analysis of retinol, niacinamide, and SPF), hair loss science (minoxidil, finasteride, hair transplants), men’s fragrance (with 80+ colognes personally tested), and body grooming techniques.
When he’s not reviewing the latest grooming products, Axel focuses on making complex grooming topics accessible and actionable for everyday guys.
