What to Wear on a Coffee Date - Milena Joy

What to Wear on a Coffee Date

  • 1
  • January 15, 2014

Coffee dates are an easy, low-pressure way to see if there is chemistry between the two of you without committing an entire evening or breaking your wallet. No one ever has more than one latte so if the date is a bust, you can get out after the last drop. Cocktails can blur your mind and your vision, but coffee has you alert and thinking clear. In fact, coffee dates are so straightforward that the biggest stress you will have is what to wear on your coffee date?

Coffee Date Couple

MEN: Dress for the date you want, not the date you’re having.

While your instinct might be to throw on your favorite t-shirt and jeans which is also what you might wear to meet your buddy, you may want to consider that showing up like that might just land you another buddy. Instead, step it up from the bromance coffee date and wear something that could transition to a dinner date if everything goes well. You don’t want your clothes to hold you back from taking that next step.

A bad first impression can also keep her from saying “yes” to a second date. If it looks like she’s just another stop on your Saturday check list, she may write you off before you get the opportunity to take her on a real date. Women pay attention to details so she will recognize your effort and will be flattered to know that you took the time to impress her.

Here a few things items in your closet that may work:

  • Casual button ups (think plaid, military, etc.), quarter zip sweaters, polo, or lux cotton fitted t-shirt
  • Dark jeans, chinos (no pleats), narrow whale corduroy, knee length shorts
  • Motorcycle style leather jackets, wool pea coats, or casual cotton blazer
  • Comfortable shoes like loafers, boots, boat shoes and spectator sneakers

Here’s what never works:

  • Anything with the name of a college or sport team
  • Anything you actually wore in college
  • Anything with a company logo or a brand name emblazoned across it
  • Anything that you can also wear to the gym or hiking
  • Anything that doesn’t fit you properly

WOMEN:  Say “yes” to the dress and keep it effortless.

This might seem contradictory, you may think of a dress as something worn on a special occasion, requiring extra effort and primping.  Well, it is a special occasion and you should put some time and thought into it, but the result should look natural and approachable or rather effortless. A day dress (think sundress for summer, sweater dress for winter) can be feminine and flirty and what guy doesn’t like that?

While your typical skinny jeans and a cute top are certainly appropriate, a dress will make you stand out from the rest of the women he’s met for coffee that week. It’s a good way to show a little skin without looking desperate or overly sexy. The key is to be memorable without looking like you are trying too hard.

Here a few things items in your closet that may work:

  • Sweater dress, wrap dress, shirt dress, t-shirt dress, or skirt
  • Perfectly fit jeans and an edgy top or a simple top accessorized well
  • Accessorize with a scarf, belt, statement earrings or necklace
  • Layering with a leather jacket, fitted cardigan or casual blazer
  • Knee-high boots, booties, wedges, ballet flats, or stylish sandals

Here’s what never works:

  • Anything that shows more skin than it covers
  • Anything you would wear to a club
  • Anything that resembles something your mom owns
  • Anything that resembles something your date might own
  • Anything that doesn’t fit you properly



Leave a Reply