wearing coat over blazer

7 ESSENTIAL STYLE TIPS FOR MEN OVER 50 BEFORE YOU SHOP

Navigating the world of fashion in your 50s (and beyond!) may seem daunting, but trust me, it’s entirely achievable. While I can’t personally guide every man receiving an AARP membership in the mail, I can offer you this comprehensive guide to dressing for mature men.

If you’re new to my writing, you might be asking yourself: Caroline, as a 29-year-old woman who spends her free time watching Nordic crime dramas and perfecting my homemade macaroni and cheese, what do I know about the style dilemmas faced by men approaching early retirement?

Well, for one, I have a soft spot for well-dressed older gentlemen.

Every man over 50 has unique wardrobe needs that reflect his personal style and lifestyle. Whether you’re searching for casual attire, looking for shopping recommendations, or simply wanting to elevate your fashion game, dressing well at this age can be just as exciting and diverse as it is for younger men.

Not sure where to begin? No need to fret! Below, 7 tips on nailing mature style for men:

Get a tailor

Everyone I’ve spoken with in the realm of men’s style, especially for those over 50, agrees on one crucial point: the difference between “a guy wearing clothes” and “a well-dressed man” often comes down to good tailoring.

Building a relationship with a tailor is essential for any mature man looking to elevate his style.

Consider your tailor your clothing’s doctor. Just as you have a dentist for your teeth, an internist for your health, and a dermatologist for those pesky moles, it’s time to have a tailor on speed dial to ensure your wardrobe is in top shape.

Now, I can already hear you thinking: “The clothes I own fit me just fine!”

But let’s be real—no man, and I mean none of you, can wear off-the-rack clothing perfectly.

Sure, you don’t need to have every t-shirt tailored or sweatpants hemmed, but those button-down shirts you wear daily with jeans or chinos? Get the sleeves adjusted to the right length.

And don’t forget about those jeans and chinos! 

What about the blazer you wear for dinner with your spouse each week? Could it use a little adjustment to fit you better?

Think of this process like visiting a doctor. You don’t go in every day for every little issue, but for the significant matters, you want to consult a professional. 

Focus on the finishing touches 

When it comes to presentation, the key differentiator between well-dressed men and those who simply wear clothes is the extra attention to detail. These subtle touches may not be immediately noticeable, but once you see them, they make a significant difference.

This attention to detail extends beyond your clothing to grooming, including a well-maintained beard (and nose hairs!), clean nails and cuticles, and a pleasant scent. Just look at the smart tie and coordinating socks worn by Stanley Tucci—voted the most stylish man of 2023 by Style Girlfriend followers!

Accessories are an excellent way to elevate your style as a man over 50. A beautiful scarf can enhance a simple blue overcoat, while the right shoes can complete your outfit—just as easily as the wrong ones can ruin it.

Investing in accessories is a smart choice for your wardrobe. Timeless pieces, like a classic pair of glasses, will never go out of style, and if you choose quality items built to last, you’ll enjoy them for years to come.

I’d like to highlight timepieces: they’re one of the first things I notice on a man. If you wear a watch, I can’t help but notice which one it is.

Let me be clear: you don’t need to spend a fortune on a watch. However, if you can invest in a quality timepiece, it’s often worth it. Even an affordable tank-style Seiko can make you look polished and distinguished.

Invest in forever pieces

By avoiding fleeting trends, you can invest more wisely in your wardrobe. Why? Because when you focus on timeless pieces, you know you’ll wear them for more than just one season.

Instead of purchasing multiple inexpensive shirts and trousers, consider buying one or two high-quality staple items. Then, invest in having those pieces tailored to fit you perfectly. The final step? Embrace the ease and simplicity of cultivating a signature personal style!

Look for brands that prioritize craftsmanship and quality. 

While you may not have the budget to splurge on every item in your closet, you can be strategic about your spending.

Identify the pieces you wear most frequently. If you rarely wear sweaters but often don blazers—think of a post-presidential Barack Obama—prioritize your budget accordingly to reflect your lifestyle.

Lean into a Monochromatic Color Palette

Monochromatic dressing involves combining pieces from the same color family to create a cohesive and polished look. This style not only elongates your body but also gives you a sleek, modern appearance with minimal effort.

Take, for example, the character Steve Martin, 79, plays on Only Murders in the Building. He often sports monochromatic ensembles, like blue jeans paired with a white shirt and a blue knit sweater or overcoat.

For men over 50, these outfits are not only simple to assemble but also effortlessly elevate your style.

You can approach monochromatic dressing in a few different ways. Our favorite at Team SG is the black and blue route—opting for rich, deep blues like navy—or embracing earth tones, such as pairing tan chinos with a chunky oatmeal rollneck sweater.

Aim for leveling up your personal style instead of chasing trends

Here’s a little secret: I often share this advice with my younger clients, but it’s especially true for older gentlemen—dressing for who you are, rather than trying to keep up with the latest trends, makes all the difference.

By midlife, you’ve witnessed countless trends come and go, which makes it easier to identify which cuts and styles flatter you and which colors and textures enhance your personal aesthetic.

Consider what clothing aligns with your lifestyle and which pieces don’t quite fit who you are. 

Think of this guideline not as a limitation, but as a permission slip to bypass fleeting trends. That’s a true luxury! As men age, they naturally become more distinguished—there’s a reason the term “silver fox” is a compliment.

Allyson B. Fanger, the costume designer for Netflix’s (criminally underrated, in my opinion) *Grace and Frankie*, shared that one of the joys of dressing older characters like Robert and Sol—played by Martin Sheen and Sam Waterston, both in their eighties—is that these men have lived rich lives.

The show features two lawyers who leave their wives for each other after their kids have grown up, and their style is spot on.

Robert and Sol don’t need to evolve further in their fashion choices, which makes dressing them all the more enjoyable for Fanger.

They each have favorite brands, signature color palettes, and distinct approaches to style.

Robert is traditional, favoring button-down shirts and chinos—he’s a Brooks Brothers man through and through.

Sol, on the other hand, embodies the spirit of a hippie, opting for Cubavera camp shirts and comfortable Tommy Bahama linen pants.

These characters exemplify how, regardless of personal taste or style, it’s entirely possible to achieve top-notch personal fashion at any age.

Ultimately, knowing who you are and being confident in that is the cornerstone of any man’s style, and that understanding becomes more profound as you accumulate life experience.

Adopt a wardrobe uniform

Larry David, at 76, is a big advocate for uniform dressing. While many people think of a daily uniform as a traditional suit and tie, David exemplifies how versatile and liberating this approach can be.

He’s a king of casual style—if you’re searching for casual clothing ideas for men over 50, the *Curb Your Enthusiasm* star offers an excellent blueprint.

His go-to wardrobe staples include crewneck sweaters, zip-ups, AG 5-pocket chinos, and soft shoulder blazers. 

If the thought of choosing an outfit every day feels overwhelming, this dressing strategy might be perfect for you. 

Consider building a capsule wardrobe filled with a few pieces you love: your favorite pants, a handful of shirts that make you feel your best, and some knitwear or jackets.

And don’t hesitate to buy items you adore in multiple colors! (This is another trick David uses.)

This way, each morning, you can reach into your closet and confidently know that whatever you pick will likely coordinate beautifully.

Be yourself 

It might sound a bit silly to wrap up a list of style tips with a reminder to just accept yourself, but hear me out. You might think, “My style is just a ripped sports jersey and Crocs,” and to that, I say: maybe it’s time for a change! (Just kidding… or am I?)

What I really mean is don’t overthink dressing for a particular age. These style tips are helpful if you’re unsure where to start or want to elevate your look. But if you already have a signature style or enjoy dressing outside the norm, don’t let the number in front of your age hold you back. Embrace what makes you unique and wear it with confidence!

CONCLUSION

In conclusion, navigating style in your 50s and beyond doesn’t have to be a daunting task. Embrace the principles of good tailoring, invest in timeless pieces, and build a wardrobe that reflects who you are. Remember, personal style is all about confidence and authenticity—wear what makes you feel good, whether it’s a classic blazer or a funky shirt.

Don’t shy away from experimenting with accessories and details that can elevate your look. And most importantly, don’t let age define your fashion choices. Celebrate your individuality and express yourself through your clothing. After all, style is a lifelong journey, and it’s never too late to redefine your aesthetic!

HOW TO WEAR ANKLE BOOTS WHEN YOU’RE OVER 40

Age is just a number, and that definitely applies to style! Ankle boots are a wardrobe staple, but you might wonder if there are tricks to rocking them over 40. The answer is a resounding no! In fact, ankle boots can be incredibly flattering and versatile for any woman. Whether you’re looking for edgy, polished, or comfy-casual looks, there’s a perfect pair (or two!) out there for you. Let’s dive into some tips and outfit ideas to show off your unique style with confidence.

TYPES OF ANKLE BOOTS

Ankle boots come in a wide variety of styles, so you’re sure to find a few (or more!) that suit your taste and wardrobe. Here’s a breakdown of some of the most popular types:

Chelsea Boots: These classic pull-on boots feature elasticated side panels for a snug fit. They come in various heel heights, from flat to platform, and can be dressed up or down.

Combat Boots: Channel your inner rockstar with a pair of combat boots. These boots typically have a lace-up closure, a thick sole, and a round toe. They add a touch of edge to any outfit. 

Ankle Booties: Ankle booties are a more delicate take on the ankle boot. They often have a shorter shaft, a pointed toe, and a stiletto or kitten heel. They’re perfect for dressing up a skirt or dress. 

Chunky Heel Boots: These boots offer both style and comfort with their thick, block heel. They’re perfect for all-day wear and can be dressed up or down.

Loafers Boots:  Loafers get a stylish upgrade in boot form. These boots typically have a lace-up closure and a moc-toe design. They add a touch of polish to any outfit. 

Sock Boots:  Sock boots hug your legs like a sock, creating a sleek and streamlined silhouette. They come in various heel heights and materials, making them a versatile option. 

Western Boots:  For a touch of country flair, consider a pair of western boots. These boots typically have a pointed toe, a slanted heel, and intricate stitching. 

STYLING TIPS FOR ANKLE BOOTS

TRY SOME CROPPED PANTS WITH A NICE BLOUSE

Cropped pants and a blouse are a match made in outfit heaven, and ankle boots are the perfect partner to complete this look. The cropped pants will showcase your boots, adding a touch of polish and elongating your legs.  For a more relaxed vibe, choose a flowy blouse that drapes over the waistband of your pants. If you’re aiming for a polished look, try a tucked-in blouse with a fitted silhouette. Don’t be afraid to experiment with textures and patterns! A silky blouse adds instant sophistication, while a patterned blouse can inject some personality into your outfit. No matter your style, this combination creates a flattering and versatile look that works for work, weekend errands, or a night out.

CUFF YOUR JEANS TO SHOW OFF YOUR BOOTS

Cuffing your jeans is a stylish technique to showcase your favorite ankle boots, adding a touch of effortless coolness to your outfit. To achieve the perfect cuff, consider your jean style – straight-leg and boyfriend jeans work well for cuffing, while skinny jeans can be cuffed with a smaller, single fold to avoid bulkiness. Aim to reveal a sliver of ankle, about an inch or two, for a balanced silhouette. Choose between a double cuff for a polished look or a single cuff for a more relaxed vibe, and experiment with different cuff widths and heights to find what suits you best. Ironing the bottom hem beforehand ensures a clean, crisp fold that stays put all day. Ultimately, cuffing is a personal style choice that allows you to play with proportions and highlight your footwear in a way that feels uniquely you.

PAIR A PATTERNED T-SHIRT DRESS WITH SOLID ANKLE BOOTS

Ankle boots can make a simple outfit look more interesting. A T-shirt dress is comfy and cute, and to make it even better, you can add some extra stuff. You can wear heeled ankle boots to make it more girly or flat ones like Doc Martens to make it cooler. Also, add some nice jewelry like a necklace and bracelet. If you wear a belt, it can make you look more stylish and show off your body shape. Plus, wearing ankle boots with heels can make your legs look longer!

SPICE UP A SWEATER DRESS WITH COMBAT BOOTS

Adding combat boots to your cozy sweater dress can make your outfit look really cool! Here’s how to do it:

First, make sure your dress isn’t too loose. Wear a tight top underneath, like a turtleneck or a fitted T-shirt. This will balance out the baggy look of the dress. Next, add some edgy accessories. A leather jacket, chunky scarf, or a bold belt can give your outfit some attitude. A crossbody bag with a rock-and-roll style will complete the look. Don’t forget about tights! They can totally change the vibe of your outfit. Try opaque tights for a warmer feel, fishnet tights for a grungy look, or sheer tights if you want to show some skin while still keeping the edgy vibe. Lastly, have fun with your jewelry. Combat boots can handle bold pieces, so layer on some chunky necklaces or statement earrings to complete your cool look!

WEAR WIDE-LEGGED TROUSERS AND HEELED BOOTS

Wearing wide-legged pants with heeled boots is a great fashion choice that makes you look awesome without much effort. Here’s how to do it: First, pick boots with heels that make your legs look longer, like stilettos or block heels. It’s up to you if you want to get your pants tailored to fit neatly over your boots. For tops, you can try tucking in a tight shirt for a neat look, leaving a loose blouse out for a relaxed style, or wearing a short top with a jacket for a trendy vibe. Keep your accessories simple and stylish, like a nice belt to show off your waist and some pretty jewelry to finish off your outfit. Follow these tips, and you’ll rock this cool and flattering outfit!

STAY WARM IN A TRENCH COAT AND CHUNKY BOOTS

A trench coat and chunky boots are a powerful combo for conquering chilly weather in style. The trench coat, with its wind-resistant fabric and optional belt, acts as your first line of defense. Layer chunky knits or turtlenecks underneath for added warmth. Don’t be afraid to play with textures! A chunky cable-knit sweater adds a cozy element, while a sleek cashmere turtleneck provides a more polished look. Chunky boots provide both insulation and traction, keeping your feet toasty and secure on slippery surfaces. For extra warmth, consider adding thermal socks or layering thinner socks underneath. With this winning combination, you’ll be ready to embrace the crisp air while looking effortlessly stylish.

WEAR ANKLE BOOTS WITH A BLAZER AND MINI SKIRT

Ankle boots, a blazer, and a mini skirt are a fashion trifecta, creating a look that’s both effortlessly chic and undeniably cool. It’s all about balance! Pair a slightly shorter mini skirt with a blazer that hits at the mid-thigh or goes longer for a more polished feel. This creates a flattering silhouette that’s both playful and sophisticated. When it comes to footwear, ankle boots offer endless possibilities. Stilettos add instant leg-lengthening drama, while chunky heels provide comfort and a grounded vibe. Kitten heels strike a perfect balance between style and wearability. Complete the look with tights for cooler weather or bare legs with patterned or sheer tights when the temperature allows. Keep accessories minimal and elegant – a delicate necklace or statement earrings will add a touch of personality without overwhelming the outfit. A clutch or crossbody bag finishes the look for a night out, while a tote bag adds practicality for daytime adventures. This outfit formula is a timeless winner, ready to take you from work to weekend with just a few tweaks.

PAIR POINTED-TOE ANKLE BOOTS WITH WIDE-LEGGED JEANS

Wearing wide-legged jeans with pointed-toe ankle boots makes you look really good. The pointy toe of the boots makes your legs look longer and balances out the wide jeans. It keeps the focus on your ankles and gives you a modern style. You can wear this combo for different occasions, whether you want to dress up with a nice blouse and jacket or keep it casual with a t-shirt and leather jacket. Either way, the pointed-toe ankle boots add a fancy touch to your outfit.

TRY SKINNY JEANS WITH FUN, PATTERNED ANKLE BOOTS

Breathe new life into your trusty skinny jeans with a dose of playful personality! Fun, patterned ankle boots are the perfect way to add a unique touch to your everyday outfit. Let these statement pieces be the stars of the show.  Pair them with a simple, solid-colored top in a neutral tone like black, white, or gray. This ensures the boots take center stage without any competition. When it comes to the patterns, the world is your oyster! From bold florals and geometric prints to playful animal textures, choose a design that reflects your personality and complements your existing wardrobe. Remember, with patterned boots as your statement piece, keep accessories minimal and elegant. 

WEAR ANKLE BOOTS WITH TAILORED TROUSERS AND A CABLE-KNIT SWEATER

Ankle boots, nice pants, and a warm sweater make a classic and stylish outfit that you can wear to work or on the weekend. The pants should fit well and make your legs look good with the boots. Choose boots that match the outfit, like cool Chelsea boots, fancy heeled boots, or chunky heels. For accessories, pick eye-catching pieces like a necklace or earrings, and keep your bag simple. You can change your accessories or add more clothes to stay warm when you switch from work to the weekend.

ROCK JEANS AND A T-SHIRT FOR A TIMELESS, CASUAL LOOK

The jeans and t-shirt combo is a fashion staple for a reason – it’s effortless, stylish, and endlessly adaptable. This timeless pairing is perfect for casual outings, errands, or just relaxing at home. The beauty lies in its versatility.  A crisp white tee and dark wash jeans create a clean and classic look, while a graphic tee and ripped jeans add a touch of personality. No matter your style, there’s a jeans and t-shirt combination that works for you.  With the right shoes, you can take it anywhere. Sneakers keep it casual, while boots or heels can add a touch of polish. So next time you’re reaching for something comfortable and stylish, remember the timeless appeal of jeans and a t-shirt.

PAIR FAUX LEATHER WITH ANKLE BOOTS FOR AN EDGY LOOK

There are endless ways to rock this edgy combination.  Think sleek faux leather leggings paired with chunky combat boots for a street-style vibe.  For a more polished look, try a faux leather skirt with pointed-toe ankle boots and a tucked-in blouse. Don’t be afraid to experiment with textures and colors.  A glossy black faux leather jacket adds instant cool to a simple tee and jeans, while a wine-colored faux leather skirt paired with neutral boots creates a rich and sophisticated edge. 

WEAR ANKLE BOOTS WITH A WRAP DRESS IN WARM WEATHER

You can wear ankle boots with a wrap dress even when it’s warm outside! It’s a stylish choice for sunny days. Just remember a few things: Choose a wrap dress made of light fabric like cotton or linen to stay cool. A shorter dress looks nice with ankle boots and gives a relaxed feel. Pick ankle boots that are light and summery, like ones with cutouts or sandals with ankle straps. If it gets chilly in the evening, you can add a light jacket over your dress for extra warmth and style. With these tips, you’ll look fashionable and feel comfortable in your ankle boots and wrap dress combo, even in warm weather!

SHOW OFF YOUR CONFIDENCE WITH A BODY-CON DRESS

Ankle boots complement this fitted style perfectly. Show off your figure by pairing a mid-length black body-con dress with a leather jacket and heeled ankle boots, guaranteeing attention-grabbing style. Complete the look with chic sunglasses for that ultimate fashionista vibe. According to fashion expert Joanne Gruber, confidence is key in your outfit. “Your style starts with how you feel inside,” she emphasizes. When you wear your outfit with confidence and feel fantastic in it, that’s when you truly shine.

ROCK A BOMBER JACKET AND GRAPHIC TEE FOR A YOUTHFUL LOOK

Show off your unique personality with graphic tees, a comfy choice to express your interests, such as your favorite band. Add a touch of edginess to your outfit with a bomber jacket. For a rocker vibe, pair it with ankle-length combat boots, or opt for ankle boots with a bit of a heel to add a feminine twist.

CONCLUSION

As you can see, age is just a number when it comes to rocking ankle boots! With a variety of styles to choose from and endless outfit combinations, there’s a perfect pair (or a few!) waiting to be incorporated into your wardrobe. So don’t be afraid to experiment, embrace your personal style, and strut your stuff with confidence. After all, fashion is all about having fun and feeling fabulous, and ankle boots can be a key player in achieving that for any woman over 40.