Stylish Outfits for Men

December 18, 2019 8 min read

Stylish Outfits for Men

From your day-to-day life to special occasions, it's essential that you have an outfit that's just right. If you often find yourself standing in front of your closet, not sure what to wear, having a few outfit templates in mind can help you out. 

Take a look at a few men's wardrobe builder outfits that can make you look good and feel confident in the clothing you're wearing. Once you have the basic outfit formulas down, you can find ways to modify them to match your personal style.

1. Sports Coat, T-Shirt and Jeans

If you're looking to look put together, but not too formal, the combination of a sports coat, tee and jeans give you a smart-casual look. Jeans, sports jacket and a tee is a pretty versatile, good guy outfit idea, as you can wear to the office, on a date or out on the town.


  • Sports Coat. The best sports coat will be unstructured and single-breasted. A custom tailor can help you select the perfect color to complement the rest of the outfit and make sure it fits just right.
  • TeeFit-wise, look for a t-shirt that isn't too tight, but that also doesn't have a loose-fitting, sloppy look either. The Robert Barakett T - V Neck is a great option, as it fits great and comes in multiple colors, including black, white, navy and charcoal.
  • JeansTo look like you know what you're doing, you'll want to get a pair of dark jeans to tie the whole outfit together. To keep it more casual, you can go with the Wrangler Stretch Jean - Dark Denim. For a more formal look, the Wrangler Dress Jeans - Black should be your go-to pick.
  • AccessoriesA basic leather belt works well with this outfit. For footwear, a Johnston and Murphy - Copeland Chukka is a stylish option.


2. Deck Shirt And Khakis

When to Wear Deck Shirt and Khakis

If you're looking to go boating or are spending the day out at the golf course, a deck shirt and khakis create an outfit that is both classic and modern.


  • Deck Shirt. A deck shirt is the most important part of this outfit, as its the most eye-catching part of it. The Nautica Deck Shirt comes in a variety of colors that look great. If you're out boating or attending a garden party, the deck shirt's breathability, moisture wearing technology and SPF protection will be a welcome addition.
  • KhakisThe Docker Signature Khaki D2 - Straight Fit - Khaki complements the deck shirt. The right fit will make sure that the khakis aren't too loose or slim. The No Wrinkle® finish will keep you looking composed throughout the day.
  • ShoesA pair of Dockers - Montclair Loafers are an excellent fit for khakis. Though they are easy to slip on, they still have a stylish, high-class look to them.


3. Linen Pants, Hawaiian Shirt and Sandals

If you're heading down to the beach for a vacation and want to look your best, linen pants, a Hawaiian shirt and sandals are the way to go.


  • Linen PantsMerc 100% Pure Linen Pants are designed to be worn in the tropics and on a beach. Their breathability and soft, linen material give them superior comfortability over other pants. Along with the comfort they provide, linen pants can give you a classy appearance even when you're lounging in a beachside hammock.
  • Hawaiian Shirt. Unlike Hawaiian shirts of the past, a Tori Richard's Hawaiian shirt is a luxurious option that is eye-catching and attractive. If you're searching for a shirt to wear, the Tori Richard - Good Reef shirt is incredibly comfortable and made out of only the most high-quality cotton lawn material.
  • Footwear. The Stacy Adams - Argosy sandals pair well with linen pants thanks to their relaxed look. Though casual, the sandals are more formal than flip-flops.


4. Overshirt, Jeans and a T-Shirt

Casual Overshirt, Jeans, and T-Shirt

If you're trying to keep things casual while still going for a more dressed up look than just wearing a t-shirt, an overshirt is a perfect fit for you. Combining it with your favorite pair of jeans and a T-shirt will keep you warm on a chilly night and let you send the message that you care about looking good, even when dressed more casually.


  • OvershirtAn F/X fusion plaid shirt pairs well with a plain colored T-shirt. The plaid design can come in navy, green or burgundy colors. The shirts are made out of 60% cotton and 40% polyester, making them easy to care for and warm to wear. The shirts look good buttoned up or left unbuttoned, with the sleeves rolled up to the elbow.
  • T-ShirtJockey Crew Neck t-shirts are often used as undershirts beneath dress shirts, but they also look great with overshirts. The reinforced collars retain their shape, meaning that they will hold up over time. Along with Jockey Crew Neck shirts, you can also use a Robert Barakett T - V Neck if you're looking for a shirt with a wider variety of colors.
  • Jeans. Darker jeans are a solid choice to pair with an overshirt and T-shirt. The Levi 505 - Black is one of the best options available today. It comes in a classic straight leg style that fits all body types. If you want a navy color, you can use Levi 505 - Rinsed jeans. They look stylish on all body types and are made out of high-quality 100% cotton.


5. Guayaberas, Jeans and Western Boots

Guayaberas have a long history, as the first version of the shirt comes from 18th century Cuba. Over the years, the shirt has evolved and gained popularity. It looks great when worn with western-style boots and jeans.


  • Guayaberas. The Presidente Guayabera Long Sleeve will turn heads thanks to its intricate embroidery and stylish pleats. It's incredibly versatile as well, as it can be worn to weddings, to church or out with friends.
  • Pants. For a more casual look, you can go with a light or dark pair of jeans. If you're going to a more formal occasion and want to wear your guayabera, the shirt pairs beautifully with slacks. The Slacks - Plain Front will be an excellent choice.
  • Boots. When you wear a guayaberas shirt, the most natural piece of footwear is a western-style boot. The Dan Post Milwaukee Leather Western Boots have a cowboy heel, iconic western stitching and a pointed toe. The boots are the finishing touch to your outfit, making you feel and look the best. If you're wearing slacks instead of jeans and looking for a more formal appearance, a variety of Stacy Adams - Datyons can look great.


6. White Dress Shirt, Black Jeans and Boots

A crisp white dress shirt combined with black jeans and boots is a classic style. Black and white is an iconic combination that's been long used to give the wearer a dapper appearance. Today, you can combine a casual, slim fit shirt with black jeans and modern boots for an attractive everyday outfit.


  • White Dress Shirt. A slim-fit white button-down shirt is a key part of the outfit.  The shirt shouldn't be overly tight, but it should give shape to your torso. Since the shirt is meant to be worn untucked with black jeans, its length is also key to looking your best. The David Donahue - Dress Shirt - White provides a tailored, crisp appearance to anyone wearing it and is even more attractive paired with black jeans.
  • Black Jeans. Black straight fit jeans make the white dress shirt pop. Levi 505 Black jeans are a popular pick.
  • Boots. A pair of boots complements the rest of the outfit nicely. Stacy Adams - Madison Cap Toe Boots are a masculine and stylish option. Another pick, for a sophisticated appearance, are the Florsheim Duke Zipper Boots. The boots offer extended heel and shaft heights, so you're sure to find the style and fit that works for you.


7. Long-Sleeved Shirts and Shorts

If the weather's warm, but you still want to look cool, a pair of shorts combined with a long-sleeved, button shirt can keep you looking sharp and distinguished.

  • Long-Sleeved Shirt. For your shirt, choose a button-down made out of linen, a lightweight cotton or a linen-cotton blend that will keep you cool on a hot summer day. The David Donahue - Sport Shirt - Merlot/Gold is made out of 100% cotton and designed to maximize your comfort with a spread collar and two back pleats. It's also a fun, multi-colored shirt perfect to wear on a sunny afternoon.
  • Shorts. A pair of Savane Flat Front Shorts work with both T-shirts and dress shirts, making them an excellent choice for a variety of occasions.
  • Accessories. For your footwear, boat shoes and loafers are likely to be your best options. A pair of Dockers - Lakeport Boat Shoe can look quite attractive with a pair of shorts. Whether or not you're planning on wearing your shirt tucked or untucked, you'll also need a belt to support the rest of the outfit. One of the best options you can choose will be the tan Brighton - Sedona Belt, as its leather and silver-plated buckle will accent the rest of your look.


8. Light Blue Jeans, White Crew Neck Tee and Sports Jacket

Jeans, White T-Shirt, and Sports Jacket

If you're looking for a semi-casual look that you can walk the city in, there's nothing better than a pair of light blue jeans with a white T-shirt and a sports jacket.


  • Light Blue Jeans. A pair of Levi 505 - Stonewashed jeans are an excellent choice. Their light-blue, stonewashed appearance complements the white T-shirt and makes a statement. Pair the jeans with white shoes, and you'll have a winning combination.
  • White Crew Neck TeeThe Jockey Crew Neck is a great shirt to pair with the jeans and the jacket. It looks good tucked and untucked, while also offering superior fit, comfort and quality.
  • Sports Jacket. There are several jacket options you can choose from that look great with this look. A tailor can help a stylish casual jacket fit you perfectly, complementing the rest of the outfit.


9. Black Dress Pants, Wine Colored Shirt and Oxfords

 For a dependable outfit that you can rely on for more dressed-up occassions, go with black dress pants, a wine-colored shirt and black oxfords.


  • Dress PantsBallin's 100% Italian Wool Plain Front Plants are sophisticated and lightweight, providing comfort while also impressing anyone who sees them. A pair of quality black dress pants are key to any man's wardrobe. You can be confident you're getting the best with what Ballin has to offer.
  • Wine-Colored Shirt. Bugatchi Wine is one of the most attractive dress shirts on the market today. Its wine color is unique and sure to stun anyone who sees you wearing it. With it, you can go to the office in style or head out on a first date feeling confident.
  • Oxford Shoes. To go with the attractive dress pants and shirts, you should add a pair of oxford shoes. A pair of black Florsheim - Postino Cap Toe Oxfords enhances the look of your entire outfit. Their classic cap toe finish and cool embossed accent add to their appeal and make them a stylish addition to your wardrobe.


10. A Custom-Tailored Suit

A custom-tailored suit is an important addition to any guy's closet. There's a pride that comes with wearing something that you had direct input in making and that has been created with your style in mind. Due to the confidence that a custom suit will give you, you'll want to invest in one to complete your wardrobe.


Interested in Building Your Wardrobe?

Good Outfits for Guys at Penner's

There are a variety of good outfits for guys at Penner's, both online and in-store. A store associate can help you add to your wardrobe and find styles that match the look you're hoping to cultivate. If you want a customized suit, Penner's is ready to be of assistance and will tailor a suit that meets your needs.

Please feel free to come into the store for free custom tailoring and to speak to one of our experts. Many of the custom tailors at Penner's have over 25 years of experience at the store and know fashion inside and out. If you have any questions, please give us a call at 210-226-2487 to speak to one of our knowledgeable representatives.