Men's Guide to Dressing in Your 40s

May 22, 2025 5 min read

As a man in your 40s, you're transitioning into a phase of life where you've established your career and care less about what other people think. Welcome to the age of authenticity and quality of life. The only thing missing is a wardrobe that matches this new era.

Men in their 40s are perfectly poised to create a closet that combines the best elements of every decade into one cohesive aesthetic. We're talking effortless fashion that is traditional yet modern. Pieces that are functional and relaxed but still polished.

It's time to reinvent yourself. Our men's guide to dressing in your 40s will help you take features of your style that appeal the most to you and refine them using standards that will never go out of style. 

1. Build a Strong Foundation

The key to a great wardrobe is versatility in basic pieces. You can achieve this by investing in staple pieces you can build on, starting with the foundation of a capsule collection.  

Mixing and matching is the name of the game, and basic, quality essentials are the best way to create smart fashion looks. For example, you can choose one quality shirt and purchase it in five colors. Add a pair of khakis and jeans, and you have 10 unique outfits to wear. Your options will increase when you add cardigans, pullover sweaters and jackets to the mix.   

When rebuilding your wardrobe for dressing in your 40s, these are the must-haves to set you up for style success:

  • Quality suits: Nothing makes a man look better than a quality, tailored suit. To maximize the number of outfits you can mix and match, you should have four suits in tan, blackgray and navy, each complete with a vest and jacket.
  • Shirts: Five well-fitted, high-quality dress shirts and five casual button-downs will cover most occasions. The classic colors are white, light blue, pink, white and blue stripes and a checked shirt of your choice. 
  • Pants: Start with two pairs of jeans, two khakis and two pairs of formal pants in a range of dark and neutral colors. Combined with your shirts, these allow you to create dozens of formal and casual outfits, as well as stylish combinations that are formal on top and casual below or vice versa.
  • Shoes: You should have shoes for every occasion. Consider staples such as loafers, white sneakers, boat shoes, oxfords and boots.
  • Outerwear: Cover formal events and cooler weather with a navy blazer, winter coat, leather jacket and sport coat.
  • Knitwear: Two sweaters or cardigans create possibilities for stylish layering and cozy comfort in winter.
  • Casual wear: You can look great while relaxing by purchasing five casual, short-sleeve shirts in different colors and styles. These could include short-sleeve button-downs, polo shirts and high-quality T-shirts. Compared to graphic tees, minimalistic designs are more versatile and suited to a mature gentleman. When it comes to casual wear, go for structured cuts in pristine condition. Avoid the "just rolled out of bed" look by keeping your shirts clean, ironed and folded.
  • Accessories: Intentional functional accessories show special attention to detail. An heirloom watch, fashionable black and brown leather belts, sunglasses that complement your face shape and a quality wallet are always worth investing in.

2. Stick to the Classics

A younger, less experienced man allows trends dictated by others to influence his fashion choices. But you know better. Fads fade away, but classic looks are the North Star of clothing styles for men over 40.

Ignoring popular fashion trends and sticking with timeless basics is a sign you've evolved past fast fashion and caring about what everyone else is wearing. You don't have to look at magazines to know how to dress well — you're already there. 

3. Streamlined Footwear

You could argue that men's fashion begins with fashionable footwear. You can tell a lot about a man by his shoes, and chunky sneakers are the furthest thing from stylish footwear.

Your shoes should be minimalistic with simple lines and formed to your foot. Clean white sneakers can be elevated by business casual outfits or dressed down for relaxed looks. They give you a cool, breezy demeanor with minimal effort. Neon colors, loud patterns and shoes with blue denim should all be avoided.

4. Skip the Cargo Shorts

As a mature man, it's time to throw away your cargo shorts and pants for good. They often look outdatedand the extra pockets are generally unnecessary. There are more stylish pants that offer equal comfort and convenience.

5. Dress for the Season

When it comes to fashion, the weather forecast is your best friend. Every season offers a range of wonderful options for tops, bottoms, shoes and accessories. A new season is another opportunity to show off your best features in a fresh way.

Dressing appropriately for the season shows you are mentally present, consciously aware of your presentation and prepared for any season or occasion.

6. Tip Your Hat to Your Most Stylish Decade 

A hat does more than shelter you from the elements. It's a stylish way to personalize any outfit for a distinctive yet elegant impression. 

Though snapback baseball caps are a fun casual option, embracing your 40s is an exciting opportunity to experiment with more sophisticated options. These include:

  • Straw or felt fedoras
  • Panama hats
  • Stetsons
  • Flat caps 

Try on several hat styles to find your favorites. As a guideline, if you have an oval-shaped face, you can pull off most hat styles. Men with rounder faces benefit from hats with taller crowns or those with angular shapes like fedoras. Men with angular or heart-shaped faces tend to look best in wider-brimmed hats, like Panama hats and stetsons. 

7. It's All in the Details

A little effort goes a long way when it comes to the small details. Belt buckles and pant lengths, along with your hair part and beard length, are just a few examples of where the smallest details make the biggest difference.

Take care in choosing your accessories, maintaining your hygiene and wearing appropriately sized clothing. Think about the overall presentation, from top to bottom. The acute awareness of these details will contribute to the lasting impression of your outfit in any given situation.

8. The Same Rules Apply to Athletic Wear

This rule needs no further explanation. Just because your gym gear is made of different fabrics and more relaxed cuts doesn't mean your outfits need to look sloppy. Neutral colors, simple cuts, functional footwear and polished clothing will keep you looking fresh even while working out.

9. Tailor Your Clothes

There is something special about clothing that is made to fit your body perfectly. Tailoring your clothing automatically makes it look more high-end with neat and crisp lines that flatter your shape and size. This doesn't mean your clothing needs to be skin-tight. Instead, your clothes should follow your natural lines and complement your proportions.

10. Be Yourself

Instead of dressing like the person you once were, own the elegant masculinity you've evolved to embody. Your 40s invite you to become the most mature, dignified and stylish version of yourself. But this version should still be you. By following our essential style guidelines and investing in some timeless pieces, you can create looks that make you feel comfortable and confident. As your most dapper decade begins, exploration will sharpen your sense of what it means to double down on being you.

Evolve Your Wardrobe at Penner's - San Antonio

After four decades of life, you deserve to look and feel your best by wearing quality clothing made with you in mind. With over 100 years of experience in the men's fashion worldPenner's has earned a reputation for attire that meets this high standard.  

Penner's is a 10,000-square-foot premier men's clothing store in San Antonio, Texas. Our century-long legacy of style and staff's decades of staff let us recommend timeless looks from our unrivaled selection of high-quality menswear. This selection includes the widest range of guayaberas, shirts, pants, suits, sport coats and accessories to ensure every man who walks through our doors can find wardrobe essentials to evolve his closet. And if you're looking for the perfect fit, we provide free expert tailoring when you purchase from the store, so you'll always leave feeling like the best version of yourself.

Call our friendly menswear professionals in San Antonio at 210-226-2478 to discuss your fashion needs or browse our full catalog of apparel today.