65 Fashionable Untucked Shirts – Casual and Semi Formal Looks for Men

Okay so you want to wear an untucked shirt, but you’re unsure of how to style it? Don’t worry, we’re here to help. Firstly, when can a shirt be worn untucked? Well, that part is easy – just look at the hemline of the shirt. If it has a short, even hem, like a polo shirt, then it is designed to be worn loose and not tucked in. But if your shirt has an uneven hem with “tails” at the back or sides then it should be tucked in.

Button up shirts, t-shirts, and polo shirts are often worn untucked for a relaxed, laidback feel. They are really comfortable while at the same time, very stylish. So if you’ve been wondering what type of outfits you can fashion with trendy untucked shirts just check out these 65 examples:

# 1 Keeping it Casual

This dark indigo shirt and light colored chinos is an easy outfit to put together. Keep the shirt untucked for a low key look and add some on trend white sneakers.

# 2 Downtime Duo

This model is wearing a modern paisley button down shirt with mother of pearl buttons over gray turned up trousers and brown laced loafers.

# 3 Office Wear

Dark pants with a crisp, light colored shirt is always a good look for the office. Instead of boring black why not try a royal blue shade like this? He’s wearing it with an untucked finely detailed duck egg blue shirt.

# 4 Casual Dapper

When you want a casual style that’s still tidy think dapper for a little inspiration. Try simply styled looks like this one; a red patterned shirt, olive brown trousers, and two-tone shoes. To top it off why not get a dapper hairstyle too?

# 5 Everyday Dandy

This model is wearing a studious type outfit with an untucked plain white top. He’s got on dark colored pants and a buttoned maroon knit blazer.

# 6 Checked and Tidy

Untucked doesn’t need to mean untidy – just make sure you’re doing it with the right type of shirt. This black and blue checked number is a fine example, worn here with a fresh white t-shirt underneath.

# 7 Skinnies Style

This handsome gentleman is wearing black loafers with ankle length skinnies and a button down white shirt. The man bag and hipster shades complete the look perfectly.

# 8 Fresh Outlook

For a cool and casual look create outfits with whites and muted shades. This model is wearing a long sleeve fitted white number with pale blue skinny jeans and white shoes.

# 9 Always in Style

Check shirts are always in style and look good untucked over jeans like we see here. This model completed his look with aviator shades and a streetwise black cap.

# 10 Classy Casual

Every man should have a crisp white cotton shirt in his wardrobe together with a well fitting pair of blue jeans. It’s an easy outfit to put together and it always looks classy.

# 11 Monochrome Magic

No need to tuck your top in for this outfit. It consists of ripped black jeans and black shoes, a long sleeve white striped shirt and a puffy black gilet on top.

# 12 Urban Check

Relax in this sexy outfit – a red and blue lumberjack checked shirt, blue jeans, turned up at the ankles, and brown slip-on shoes. Add sunnies like his for a relaxed urban style.

# 13 Black and Blue

This model is wearing a light blue long sleeve shirt, folded up to the elbows with the middle buttons done up. He’s wearing it untucked over a pair of sleek black pants. Blue and black is always a winner!

# 14 Stylish Neutrals

Open collars like this will help keep you cool and looking cool. In this picture, the model is wearing a lightweight outfit with a subtly patterned white shirt over ankle-length cream skinny jeans.

# 15 Refined Street Style

Steal this model’s look and get your business done in style. Just add a modern blue pinstripe shirt over a navy pair of trousers. No need to tuck in your top or add a tie to this one.

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# 16 Slimming Sky Blue

If you want a slimming look, try dark colors on top with lighter shades below. This summer sky blue fitted shirt is a perfect example – it smoothes over imperfections effortlessly and creates a sleek shape.

# 17 Cotton Crazy

Cotton shirts are breathable and eco-friendly, making them perfect for everyday smart casual looks. This model is wearing a slim fit long sleeve dark indigo shirt with pants in a slightly darker shade.

# 18 Long and Layered

This classy long sleeve layered shirt is too handsome to wear tucked in. We love the ultra-flattering cut of this shirt, combined with a simple pair of dark charcoal trousers.

# 19 Stripy Swag

Stripes are always on trend so don’t be afraid to have loads of striped shirts in your wardrobe. Add this long sleeve gray stripe shirt to your collection and wear it loosely over plain gray pants.

# 20 Check My Shirt

This model looks relaxed and ready for the weekend in a short sleeve purple checked shirt and dark gray linen trousers. Keeping the shirt untucked adds to the laid back feel of this outfit.

# 21 Roll Up and Untuck

This model is wearing a relaxed long sleeve dark blue shirt with the sleeves rolled up to the elbows. It’s untucked, worn over a crisp pair of white trousers. He’s added a fun bowtie as well.

# 22 Button Down Chic

Combine casuals and formals for a hip look for the office. Try a look like this model – a blue pinstripe button down shirt, with a bold white collar and a pair of smart ankle length olive chinos.

# 23 Basic Black

This trendsetting black outfit is sure to get you noticed. It consists of a sporty black cap, plain black button up shirt and jet black pants. Always make sure to check that your blacks all match when wearing an outfit like this.

# 24 Vibrant Salmon Shirt

Light up your look with this vibrant delicately patterned salmon colored shirt. Its tailored hemline allows it to be worn over your pants instead of tucked in. This model paired his shirt with dark colored jeans.

# 25 Unbuttoned, Untucked

Your freshest look for a night out is a dazzling white t-shirt, an untucked and unbuttoned blue cotton shirt and a dark gray pair of semi-formal pants. Remember to roll the sleeves up slightly too.

# 26 Dress To Impress

Dress to impress with this silky traditional white button down shirt. It will look gorgeous out in the sun; just pair it with a dark pair of trousers for an outfit that will make you look and feel amazing.

# 27 Khaki Button Up

This model is wearing a fitted long sleeve khaki colored shirt, buttoned up to the neck. The neatly curved hem makes it perfect to wear untucked over a dark pair of pants.

# 28 Silky Metallics

A metallic finish is always attractive, and that’s certainly true for this handsome silky shirt. Pair it with a pair of pants for a smarter look, or with jeans like this model for a casual laid back feel.

# 29 Relax in Style

Heading out for the afternoon with friends? Relax in style with a dapper style button down white long sleeve shirt. Add a pair of dark blue pants or fitted jeans and leave the shirt untucked.

# 30 Embroidered Elegance

This model is wearing a Ukrainian design shirt with intricately patterned embroidery down the front and on the cuffs. Together with a pair of black pants, this is an untucked look well suited to a semi-formal occasion.

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# 31 Vintage Plaid

Rock a vintage look with old school plaid shirts, like this one in red, brown and white. The model is wearing his with the sleeves rolled up, over a pair of light blue jeans.

# 32 Drinks With The Boys

This model is wearing a tailored long sleeve black shirt with double pockets over a pair of dark wash jeans. With the top button undone and the shirt untucked this is a great laid back outfit for a drinks evening with your friends.

# 33 Flannel Fashion

What a look that works as hard as you do? You can’t go wrong with flannel. Try wearing a red and blue flannel long sleeve shirt over a pair of dark blue jeans and you’ll see what we mean.

# 34 Shirt Essentials

Everyman needs shirts suitable for everyday wear, like this sand colored long sleeve shirt with a medium collar and dark buttons. It will look great with dark colored jeans like the model is wearing, or semi-formal trousers.

# 35 Checkered with Accents

A pop of color is always welcome! In this picture, the model is wearing a blue and white checked fitted shirt, with long sleeves and a pop of red color along the inner button seam.

# 36 Minimalist Black Long Sleeve

Be a minimalist in this no-nonsense long sleeve black shirt with a neat curved hemline and a rounded collar. Choose it in black like this model and add dark trousers.

# 37 Jazz It Up

Tired of boring shirts? Break out and show everyone your stylish side while still looking professional in this light blue long sleeve. It’s got a flash of colorful embroidery across the chest and a snappy round hem that it allows it to be worn untucked.

# 38 Black and White Patterned Shirt

This black cotton shirt has black and white patterned embroidery over the shoulders and down the sides as well as alongside the button line. With a busy shirt like this remember to keep the rest of your outfit simple.

# 39 Blue Detailed Red Shirt

Show off your fun side in this smart red fitted smart. It has blue detail at the collar and cuff and white buttons. He’s wearing it with a dapper style haircut and dark blue jeans.

# 40 Go Green

Green is a very relaxing and invigorating color so why not add a little fresh flavor to your wardrobe with an emerald green button up down like this? Perfect for lifting your mood!

# 41 Shirt on Shorts

Denim shorts look excellent with long sleeve tops and work well with modern checked patterns like this too. This model is wearing his blue and off-white number with the sleeves rolled up.

# 42 Polo Print

This shirt is a dark navy blue with polo print and white collar and cuff detail. It’s made of breathable cotton, which will keep you cool and looking stylish.

# 43 Double Denim

This model is wearing a denim long sleeve top, with dark denim at the top and light colored denim at the bottom. It features a comfortable rounded collar and also has a cute red button on the collar.

# 44 Comfy Two Tone

Slip into something comfortable this coming spring and try this two tone blue and gray design over a pair of faded blue stovepipe jeans.

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# 45 Statement Shirt

Be the center of attention in this eye-catching black and white design. The modern criss-cross pattern and sleek fabric is perfectly suited to those who love the limelight.

# 46 Friday Night Flare

You’ve been wearing plain long sleeve shirts all week, but on Friday night you want something different. You can’t go wrong with this gray paisley number with a trendy dark blue “dipped” effect along the bottom. You definitely don’t want to tuck this one in!

# 47 Classic Print

This classic print cream and black long sleeve shirt was given a modern touch by the addition of mother of pearl buttons and a rounded hem, which looks stylish worn over pants rather than tucked in.

# 48 Black Stripes

This model is wearing a chic dark blue fitted shirt with a black striped pattern. He’s paired it with a smart pair of dark blue jeans – lovely match!

# 49 Fitted and Patterned

Here we see a fitted white design with intricate green pattern detail and mint colored buttons. Wear it over blue jeans like this model for a superb smart casual look.

# 50 Style Statement

Make a style statement with his fun patterned white shirt. It’s guaranteed to turn heads and keep you looking on trend this season.

Untucked shirts are generally intended for weekend and casual looks, and you should never wear a shirt loose over your pants to a formal occasion (unless the top is specifically designed to be worn like that). However, as you have seen you can create smarter looks, suitable for work and semi-formal affairs. Just have fun with your look, experiment and see what works for you.

3 Rules On Tucking In Your Shirt

65 Fashionable Untucked Shirts – Casual and Semi Formal Looks for Men

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