Before you buy another pair of boots or try to make heavy jeans work in July, ask yourself when you’ll actually wear them. A piece can look fine on its own and still be a bad buy for the way you dress.
For part four of my least stylish menswear series, here are ten things I’d skip, where I make exceptions, and what I’d wear instead.
1. Boots With Both Laces and a Side Zipper
If the zipper is just there for looks, it adds clutter to a boot that already has laces. I’d buy a clean lace-up boot. If you want something you can slip on quickly, try a Chelsea boot.
2. A Backwards Baseball Cap on Repeat
I wear mine backwards sometimes, especially when I’m working out. The problem is when it becomes your default. For a casual day out, try a plain cap with the brim forward.
3. Bright White Loafers and Dress Shoes
A bright white dress shoe tends to dominate the outfit. Brown suede loafers are easier to wear with chinos or tailored trousers. I make one exception for off-white suede bucks in spring or summer. They’re a classic prep look.
4. Seersucker in Winter and Flannel in Summer
Seersucker makes sense in the heat. A heavy flannel suit makes sense when it’s cold. If the temperature makes you want to take the jacket off as soon as you put it on, start with a fabric that suits the weather.
5. Heavy Jeans on Hot Summer Days
I like denim in fall and winter. On a hot, humid day, heavy jeans can feel like a mistake before you’ve even left the house. Try lightweight chinos or linen trousers for the same easygoing feel.
6. Two Watches at Once
One watch is plenty. Pick the one that suits what you’re wearing and give it a little room to stand on its own.
7. Rhinestone-Covered Clothes
If it’s for the stage, fair enough. For everyday wear, I’d get that visual interest from the cloth itself. A textured knit or a jacket with a subtle weave gives you something to look at without the sparkle.
8. The Stingy-Brim Fedora
A fedora with a tiny brim is a very specific look. If you like a felt hat, try on a few brim widths and look at your whole silhouette in the mirror. The right proportions matter more than the name on the label.
9. A Loud Hawaiian Shirt After Dark
I like a bright tropical print in the sunshine. For dinner or a night out, I’d reach for a dark knit polo or an open-collar shirt in a quieter print. You can keep the easy fit and still look dressed for the evening.
10. Hiking-Sneaker Hybrids for Business Casual
Save the trail shoes for the trail. If you’re wearing chinos or a sport coat to work, a suede derby or a loafer usually sits better with the rest of the outfit.
Build a Wardrobe You’ll Actually Wear
These are my opinions. If you’d defend one of these picks, or think I missed an obvious one, tell me in the comments.
If you’re unsure what’s worth buying next, bring a few outfits you already wear to a free wardrobe consultation. We’ll talk through what works, what’s missing, and which pieces would give you more ways to get dressed.
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