Like a Boss

Guest Post! Men’s Quick Tips on Dressing Like a Boss on a Date

There aren’t many things in life more exciting, nerve-wracking or downright calamitous than dating. Here at menswear retailer The Idle Man, we can ensure you master one aspect of dating—dressing right. With our previous dating mishaps still fresh in the memory, these are our dos and don’ts of dressing for a date.

Don’t: Wear a Suit

We understand the temptation to wear your tailored suit to a date (after all, it does look fantastic), but this isn’t a job interview. Stick with a smart-casual theme for dating and you’ll feel more comfortable.

Do: Wear A Collared Shirt

A collared shirt ensures you don’t seem overdressed and equally saves appearing lazy, what’s more having an attractive pattern on your shirt gives you an open and charming look.

Don’t: Wear a Tie

Wearing a tie gives you the impression of trying way too hard. Just button your shirt to the top and you’re ready to go.

Don’t: Wear Dress Shoes

Dress shoes in casual settings is never a good look. Instead, wear some suede on your feet to give a more sophisticated appearance.

Do: Wear a Nice Jacket or Blazer

A smart jacket can sharpen up the rest of your outfit, it’s also important to have something to wrap around her later! (Hunt’s Note: Totally agree with the ability to look like the gentleman you are by letting her wear the jacket. Even during the summer, the AC can be CRANKING in places!)

Don’t: Wear Jewelry

Jewelry can make you appear tacky and like a showoff, so keep all your necklaces and earrings in the drawer for now.

Do: Wear a Watch

Unlike jewelry, a smart watch can add character and personality to your image without looking too flashy.

Don’t: Wear Shorts
Shorts are never acceptable dating attire. Wear chinos or dark jeans and give your legs are break from the cold.

If you continue to struggle, be sure to check out The Idle Man’s personal stylist for inspiration. Have fun!

— George Cheley

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