Dressing to (Not) Impress
There’s nothing wrong with extra thought put into an outfit, and it’s even less embarrassing when you’re hoping to catch someone’s eye. However, the more we try to impress, the harder we fall sometimes, and some choices advertise effort a little too loudly. These are 20 things men might want to reconsider before dressing for women.
1. Shirts Unbuttoned Almost to the Waist
Showing a little chest can make an otherwise ordinary button-down feel more relaxed, and there’s nothing inherently wrong with the look. But there’s a point where it stops looking accidental. Leaving four or five buttons undone on a dinner date makes it very clear that the chest hair is on display.
2. Oversized Designer Belt Buckles
Some men buy recognizable designer belts because they think luxury logos will get attention. Unfortunately, an enormous metallic buckle only garners the wrong kind of attention. If anything, they can make the price tag seem more important than the actual outfit.
3. Sunglasses Indoors
A pair of Ray-Bans can sharpen an outfit outside, but keeping them on inside a restaurant? That never blows over well. Shades also make eye contact unnecessarily difficult. Flirting relies pretty heavily on seeing someone’s face, so hiding yours isn’t the seductive move it seems.
Sebastian Coman Travel on Unsplash
4. Too Many Gold Chains
One chain peeking out can add some personality without dominating the look, and that’s what you’re going for. When necklaces of several lengths and pendants are stacked together, though, the jewelry becomes overwhelming. Wearing every ounce of gold doesn’t make anyone look wealthier or more attractive.
5. Extremely Deep V-Necks
The deep V-neck had a very enthusiastic moment in men’s fashion, but that’s dead and gone. Nowadays, guys still reach for one when they want to show off a gym-built chest—and women aren’t impressed. Once the neckline starts approaching the sternum, it can look more calculated than anything else.
6. Fake-Looking Watches
Don’t get us wrong, a flashy watch can signal success and good taste. Fake ones, on the other hand, try far harder to communicate wealth than the rest of the outfit. Women who care about watches will spot the fake immediately, while those who don’t probably weren’t waiting to inspect one anyway.
7. Shirts That Are Too Small
Some muscular men love squeezing themselves into tight polos and T-shirts. Sure, the abs are impressive, but fabric straining around the buttons and stomach rarely creates the effortless confidence you were hoping for. Clothes that properly skim the body show off a strong build without making breathing look like a chore.
8. Cowboy Hats
There are plenty of men who genuinely wear cowboy hats as part of their everyday style, and on them, the choice is completely natural. We’re not talking about them, though. We’re talking about the guys who buy one purely because they think women find the rugged cowboy image irresistible. If your wardrobe has never touched Western wear, that brand-new Stetson won’t do you any favors.
9. Multiple Rings
Men’s rings have become much more adventurous, with signet rings, silver bands, and gemstones showing up everywhere. That said, loading eight or nine of them onto both hands can distract from otherwise good styling. Accessories work better when someone can actually notice the pieces you chose.
10. Shirts With Inappropriate Slogans
A T-shirt with a suggestive joke might get laughs on a bachelor weekend, but women aren’t as eager to chuckle. Phrases bragging about bedroom skills or being a “ladies’ man” land even worse. Nobody needs your shirt to provide a preview of any so-called skill.
11. Tight Leather Pants
We all know that rock stars have given generations of men an idea about leather pants. They were supposed to be cool! They were supposed to entice women! Well, away from a stage, an ultra-snug pair can be difficult to style. Straight-leg leather trousers offer the same edge with considerably less effort.
12. A Blazer With Nothing Underneath
Celebrities love to walk red carpets with nothing but a suit jacket and a bare chest. That doesn’t mean the look should leave Hollywood. At somebody’s birthday dinner or a first date, an exposed torso lands very differently.
13. Excessive Cologne
Technically it isn’t clothing, but plenty of men treat fragrance as the finishing layer of an outfit. There’s nothing wrong with that in moderation! But even a popular scent can become unpleasant when six or seven fog up a room. Cologne is much more inviting when someone has to get close enough to notice it.
14. Designer Underwear Waistbands
Designer underwear is sort of like designer belts: they’re not as impressive as magazines make them out ot be. Some men arrange their jeans low enough to display several inches of branded elastic, but women don’t need confirmation of your undies to decide whether they find you hot.
15. Noticeable Shoe Lifts
Height-enhancing insoles are marketed to short kings everywhere, and while subtle versions are impossible to detect, extreme lifts aren’t. They change posture, gait, and the proportions of the shoe. Wearing them under the assumption that your date has strict requirements also creates more self-consciousness than confidence.
16. A Vest With No Shirt Underneath
The shirtless waistcoat has appeared on celebrities and runways—two spots where dramatic styling is part of the job. Translating that look to an ordinary night out isn’t the same. It often means committing very heavily to exposed chest, tailored fabric, and almost nothing in between.
17. An Ornate Pocket Square
We’re not talking about a thoughtful pocket square. No, we’re talking about men hoping to appear sophisticated with enormous puff folds, jeweled pins, or clashing patterns. You don’t need that stuff! Good tailoring does most of the work.
18. Driving Gloves
Leather driving gloves conjure images of vintage cars, old and a very specific kind of masculine elegance. Wearing them in a bar is where the fantasy ends, though. Unless you’ve just stepped out of your car, taking them off is usually the safer move.
19. A Silk Scarf
Men can absolutely wear silk scarves well! But purchasing a designer one solely because it seems like something a wealthy bachelor would wear comes across as studied. Personal style is more appealing once it feels like something you’d still wear without an audience.
20. “Alpha Male” Clothing
Few garments announce their intentions faster than words like “alpha,” “king,” or “high value man.” A guy may wear them hoping to project confidence, but spelling those qualities out doesn’t convince anyone they’re present. If you’re actually confident, your date will figure that out without reading it across your chest.
