Do you actually want to dress to impress? Are you in your mid-twenties or thirties and still dressing like you’re in High School? Welcome to adulthood where classic menswear isn’t just clothing; it’s armor. This advice isn’t for the faint-hearted who cling to their faded graphic tees and baggy jeans like safety blankets. It’s for the brave who dare to embrace elegance with a smirk and a wink.
Suits: The Antidote to Average
If your idea of ‘dressing up’ is throwing on a sports coat you last wore to a cousin’s wedding, it’s time for an intervention. We’re talking about suits that command respect, not snickers. Forget the ill-fitting, off-the-rack disasters. A true suit fits like it was born on you – sharp, sleek, and so stunning it’s borderline offensive to the underdressed.
Recommendation: Start with a statement suit that defies the norm. If you are not sure where to start. A charcoal or Navy suit usually works well in most occasions. If you already got those bases covered, consider going beyond. Look for suits in unconventional colors like plum or teal, or opt for bold patterns like windowpane checks. Remember, tailoring is often non-negotiable. Find a tailor who understands that you’re not trying to blend in – you’re aiming to stand out. We have a full guide on suit jacket style to check out: Men’s Suit Jacket Styles: The Craft of making Blazer, Sport Coat, and Suits look good.
Accessories: Your Secret Weapon
To those sporting a rubber wristband and calling it an ‘accessory’ – let’s chat. Accessories in the classic menswear world are your arsenal of style. We’re talking ties with more personality than your average sitcom character, pocket squares that scream sophistication, and watches that don’t just tell time; they tell the world you’ve arrived.
Recommendation: This is where you let your personality shine. Go for tie pins that are conversation starters or ties with unique textures and patterns. Remember, your accessories are the exclamation points to your outfit. Get a classic automatic watch that won’t break the budget check out our guide here for good watches: What Makes a Good Automatic Watch?: Top 5 Watches Under $500
Footwear: Step Up or Step Out
Gentlemen, your beat-up trainers just won’t cut it in the realm of refined style. Footwear in classic menswear isn’t an afterthought; it’s a declaration. Lace up some oxfords that shine with ambition, or slip into loafers that whisper suave secrets. If your shoes aren’t elevating your style, you’re just walking in circles.
Recommendation: Your shoe game needs to be as strong as your suit game. You don’t need to start with plain black Oxfords; think brogues in unexpected color combinations from Allen Edmonds or daring Chelsea boots. Your shoes should be the foundation of your outfit – solid, stylish, and never boring.
Allen Edmonds Siena Brogue Wingtip Oxford
Thursday Boot Company Chelsea Boot “Duke”
Layering: The Art of Subtlety
To those layering like they dressed in the dark – a word of advice. Layering in classic menswear is an art form. It’s the subtle interplay of textures and colors, a skillful combination that adds depth, not desperation, to your look. Think tailored vests, crisp button-downs, and sleek blazers that work together like a symphony, not a car crash.
Recommendation: Layering is your opportunity to play with textures and patterns. Mix a herringbone waistcoat from with a crisp shirt from and a sleek blazer. Add scarves with bold prints or unique knits for that extra edge. Layering is like a good cocktail – it’s all about mixing the right ingredients. For the cooler seasons this advice cannot be ignored. We have some considerations for layering in our comprehensive guide: Timeless Style 101: A Classic Menswear Guide
Tailoring: Fit or Fail
Listen up, if you think tailoring is optional, you’re playing the style game wrong. Tailoring is the difference between looking like you’re wearing dad’s hand-me-downs and owning every room you walk into. It’s not just about measurements; it’s about respect – for yourself and the art of classic dressing.
Recommendation: A well-fitted garment is the cornerstone of classic menswear. Invest in a tailor who doesn’t just alter clothes but sculpts them to your body. It’s not just about taking in a waist or shortening sleeves; it’s about crafting a silhouette that screams confidence. Not sure how to start with a tailor? We got you covered: 10 Pro Tips to Save on Tailoring
Our Advice is to Dress to Impress Regularly.
This isn’t just style advice; it’s a wakeup call. Classic menswear is a field for the bold, the brave, and the dapperly dressed. It’s time to ditch the mediocre and step into the world of timeless style. You don’t have to dress nice just for special occasions, you’re allowed to look good everywhere you go. Whether its work, the mall, the grocery store, that first date. You set your own dress code, you set your own impression. Take control of your look, you deserve it. Remember, time is fleeting, dress like you’re winning, not just participating.
