Clothing Items That Are Actually Worth The Investment
How to build a wardrobe that lasts — and works hard for you.
By Brandi Hearn, Men’s Personal Stylist
Every man asks the same question at some point: What’s actually worth spending more on?
The truth is, not everything in your wardrobe needs to come with a high price tag — but a few well-chosen investments can completely change how you look, how you feel, and how others respond to you.
Here’s where to spend smart — and why.
1. Leather Dress Shoes
Recommended: Allen Edmonds – Carlyle
If you only invest in one thing, make it a quality pair of leather oxfords or derbies — in both black and brown.
They’re the most versatile shoes in your arsenal. They pair seamlessly with suiting, of course — but also elevate dark denim, chinos, and even casual blazers.
Why it’s worth it:
High-quality dress shoes mold to your feet, age beautifully, and can last decades with proper care. If you wear dress shoes more than a few times a month, this is a no-brainer.
2. Casual and/or Dress Boots
Recommended: Crockett & Jones – Coniston
Budget-Friendly Alternative: Calvin Klein – Darsey
A great pair of leather boots instantly adds structure and edge to your wardrobe.
Go with something clean and minimal — avoid overly rugged or chunky silhouettes.
Wear them with denim on weekends, or with a suit when the weather cools down.
They’re especially useful in colder climates where function still needs to look polished.
Pro tip: Look for weather-resistant options that hold up to rain or snow — without sacrificing style.
3. Charcoal Grey Suit
Recommended: Brooks Brothers – 1818 Suit
If you only own one suit, make it charcoal grey.
It’s the most adaptable shade in menswear: appropriate for weddings, funerals, job interviews, boardrooms, and dinner dates alike.
Details to look for:
Single-breasted
Notch lapel
Double vents in the back
Tailored fit (not too slim, not too boxy)
Even if you don’t wear suits often, having one ready and fitted is a power move. You never want to be scrambling when the occasion calls for it.
4. Peacoat or Overcoat
Recommended: Ralph Lauren – Melton Wool Overcoat
Outerwear should do more than keep you warm — it should finish your outfit. A sharp wool coat adds instant sophistication and makes your casual looks feel intentional.
Choose navy or charcoal, depending on your wardrobe. Go for a clean fit through the shoulders and sleeves — nothing oversized or sloppy.
Bonus: You’ll wear it everywhere. Over hoodies, suits, sweaters, even tees. And it’ll always look elevated.
Final Thoughts
Smart style is about strategic spending. Know where to invest — and where to save — and you’ll build a wardrobe that feels elevated, intentional, and uniquely yours.
If you’re not sure where to start, I help clients refine their style and make these kinds of investments with confidence.
Brandi is a personal stylist with over a decade of experience helping men show up with confidence and ease. She offers tailored style solutions that take the guesswork out of getting dressed—so you look sharp and feel great, no matter the occasion.