How to Wear a Dress Shirt

Co-authored by Paul Julch, MA and Janice Tieperman

Dress shirts aren’t just for fancy events—they can also be the bread and butter of your everyday looks. With all the different options and dress shirt combinations, it can be a tall order to nail down the perfect outfit. No need to worry! Take a peek at this list for some tips and suggestions to help you navigate the world of dress shirts.

1

Dress professionally with a dress shirt and suit jacket.

Pick out a polished dress shirt and a nice pair of dress pants. Then, add a dash of color to your ensemble with a necktie. As an extra formal touch, slip a vest over your tie and dress shirt—or, you can skip the vest and finish off your outfit with a suit jacket.^{[1]
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- Solid dress shirts provide a nice background for patterned suits, while patterned dress shirts add an extra dimension to solid-colored suits.

2

Add a tie for professional engagements.

Always wear a tie with dress shirts that have point collars. Other styles, like the spread collar, offer a bit more wiggle room. Keep your tie centered with your dress shirt for a polished, professional look.^{[2]
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- In some outfit combinations, you may tuck your tie into a suit jacket or vest.

3

Pair a dress shirt with trousers for a polished but casual look.

Dress shirts and trousers fit into the “smart casual” and “dressy casual” categories. Dress for a smart casual event with a pair of nice trousers, a dress shirt, and loafers. For dressy casual events, wear your dress and trousers with a sport coat, along with loafers or slip-ons.
- You don’t need to wear a tie with these outfits.

4

Slip on an unbuttoned blazer to give off a casual vibe.

Leave your dress shirt untucked with the top 2 buttons undone. Layer your shirt over a pair of jeans or slim-cut pants, and slip on a blazer or suit jacket overtop. Leave the jacket unbuttoned to finish off your loose, relaxed outfit.^{[3]
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5

Dress down with a pair of jeans.

Jeans provide a relaxed, casual contrast to your dress shirt. Slip into your favorite pair, layering an untucked dress shirt over top. As a finishing touch, put on your favorite pair of tennis shoes.^{[4]
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- You could wear a dark dress shirt with a light pair of jeans, along with some white sneakers.

6

Stay cool in shorts and a short-sleeved dress shirt.

Pick out a sleek, knee-length pair of shorts. Tuck your shirt into your shorts for a more polished, professional look. If you’d prefer a more relaxed outfit, leave your shirt untucked over your waistband.^{[5]
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7

Layer your shirt under a sweater for a comfy outfit.

Slip on your dress shirt, which will act as the base of your outfit. Then, add a sweater over top. Make sure the ends of your shirt cuffs, as well as your shirt collar, are visible beneath the sweater.^{[6]
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- You might pair your dress shirt and sweater with some nice jeans and a set of sneakers.

8

Stay relaxed with rolled-up sleeves.

Keep the lower cuff button secure, but undo the topmost button. Roll your sleeve up to the middle of your forearm, creating a sleek look. For a more relaxed look, undo both cuff buttons before rolling up your sleeve.^{[7]
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9

Secure your cuff buttons for a sleek look.

Check if your cuffs have 1 or 2 buttons. If you find 2 buttons, use the loosest option on your bare arm. If you’re wearing a watch, pick the tighter button option, which puts your timepiece on full display.^{[8]
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10

Leave your shirt untucked for a laid-back look.

Let your shirttails dangle over the top of your pants. Don’t worry! An untucked shirt can still add a chic touch to your outfit.^{[9]
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- For example, you might layer an untucked dress shirt over a nice pair of pants, with an unbuttoned jacket layered over top.

11

Tuck in your dress shirt for a polished feel.

The military tuck is a simple, effective way to tuck in your shirt. Unbutton and unzip your pants, so you have a little wiggle room to work with. Tuck your shirt into your waistband and zip up your pants, leaving the button undone. Then, pinch any extra material along the sides of your dress shirt and fold it toward your hip into a pleat. At this point, re-button your pants and adjust the belt as needed.^{[10]
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- Try the underwear tuck if you’re wearing layers. With this style, tuck your undershirt into your underwear, and layer your dress shirt over top. Then, pull your pants on and tuck in your shirt.
- You can also use shirt stays, or shirt garters, to hold your dress shirt in place.

12

Undo several buttons for a casual vibe.

Leave the top 3 buttons undone on your shirt. Then, let your undershirt peek out over your unbuttoned top—this gives off a light, relaxed look.^{[11]
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13

Pick a solid shirt color for a traditional look.

White dress shirts are a safe option for most outfits. You can also change things up with a solid blue shirt, or by delving into pastel colors like pink and lavender.^{[12]
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14

Play around with patterns to add an extra dimension.

Recreate a classic look with a striped dress shirt. This garment works great when paired with solid suits. For a more casual look, venture into the realm of checked shirts.^{[13]
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- Never mix patterns within a single outfit. If your suit jacket is patterned, stick to a solid-colored dress shirt.

15

Complement your dress shirt with loafers, slip-ons, or dress shoes.

Loafers are a great option for a casual outfit.^{[14]
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16

Choose a collar style that flatters your facial features.

A point collar elongates your face, and a spread collar widens it. Point collars tend to guide the eye downward, which helps add some length to your facial features. On the other hand, spread collars point more to the sides, which helps spread out your features instead of lengthening them.^{[17]
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17

Stay comfortable with the classic fit.

The classic fit accommodates many different sizes and builds. If you’re looking for a safe, comfortably-fitting shirt, then a classic fit could be a great option for you.^{[18]
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18

Show off your physique with a slim fit shirt.

Unlike the classic fit, the slim fit offers much thinner sleeves. It also has a slimmer waist, chest, and seat. This type of dress shirt may not be comfortable for every body type—but if you really like this style, can you can always order a custom fit shirt.^{[19]
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- If the slim fit doesn’t fit comfortably at first, ask a tailor or specialty shop to extend the fabric around the back.

19

Choose the modern fit for a hybrid of slim and classic fits.

Modern fit shirts offer a nice compromise. You get larger armholes while also boasting a slim waist, chest, and seat section. If you find the classic fit too roomy and the slim fit too constrictive, a modern fit shirt might be the perfect match for you.^{[20]
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20

Wear long dress shirts for formal outfits.

Hold up the dress shirt to your chest and see how long it falls. Save the garment for fancier occasions if the hem falls below your hips.^{[21]
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21

Pick short dress shirts for casual outfits.

Measure how far the shirt goes down your chest. If the garment stops along your hips, save the shirt for more casual, relaxed looks.^{[22]
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22

Slip into an undershirt for extra security.

Undershirts are handy to wear in all seasons. In warmer weather, undershirts help protect your dress shirt from unwanted sweat splotches. In the winter, an undershirt keeps you extra toasty and insulated.^{[23]
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- Undershirts also give you a bit of freedom if you choose to leave your shirt unbuttoned.

Expert Q&A

Question

Are you supposed to wear a shirt under a dress shirt?

Paul Julch, MA
Personal Wardrobe Stylist & Speaker
Paul Julch is a Personal Wardrobe Stylist, Speaker, and the founder of Urbanite | Suburbanite, a wardrobe styling business in the San Francisco Bay Area. With over 25 years in the fashion industry, Paul works with clients to make getting dressed easier, less time consuming, and more enjoyable. Paul has years of experience in retail visual merchandising - styling windows, displays, and floor sets for Banana Republic, Gap, and Express. He also has experience styling fashion photo shoots and corporate videos. Paul holds a BS Degree in Management from State University of New York at Binghamton, an MA in Clinical Psychology from Long Island University. He also studied Interior Design at the University of California, Berkeley.

Paul Julch, MA

Personal Wardrobe Stylist & Speaker

Expert Answer

You can if you want! If you want to do a more casual look with an untucked dress shirt, wear a T-shirt underneath to make the dress shirt a little shirt jacket.
Question

Can you wear a dress shirt casually?

Paul Julch, MA
Personal Wardrobe Stylist & Speaker
Paul Julch is a Personal Wardrobe Stylist, Speaker, and the founder of Urbanite | Suburbanite, a wardrobe styling business in the San Francisco Bay Area. With over 25 years in the fashion industry, Paul works with clients to make getting dressed easier, less time consuming, and more enjoyable. Paul has years of experience in retail visual merchandising - styling windows, displays, and floor sets for Banana Republic, Gap, and Express. He also has experience styling fashion photo shoots and corporate videos. Paul holds a BS Degree in Management from State University of New York at Binghamton, an MA in Clinical Psychology from Long Island University. He also studied Interior Design at the University of California, Berkeley.

Paul Julch, MA

Personal Wardrobe Stylist & Speaker

Expert Answer

Absolutely. Untuck your dress shirt, have it unbuttoned, or wear a T-shirt underneath it to rock the casual look.
Question

Does tucking your shirt in make you look thinner?

Paul Julch, MA
Personal Wardrobe Stylist & Speaker
Paul Julch is a Personal Wardrobe Stylist, Speaker, and the founder of Urbanite | Suburbanite, a wardrobe styling business in the San Francisco Bay Area. With over 25 years in the fashion industry, Paul works with clients to make getting dressed easier, less time consuming, and more enjoyable. Paul has years of experience in retail visual merchandising - styling windows, displays, and floor sets for Banana Republic, Gap, and Express. He also has experience styling fashion photo shoots and corporate videos. Paul holds a BS Degree in Management from State University of New York at Binghamton, an MA in Clinical Psychology from Long Island University. He also studied Interior Design at the University of California, Berkeley.

Paul Julch, MA

Personal Wardrobe Stylist & Speaker

Expert Answer

In general, tucked-in dress shirts are more flattering because they show off your waist.