3.7 min readBy Published On: November 15th, 2011Categories: Lifestyle, Style and Shopping0 Comments on Date Night Fashion

shopping & style

Written by Cintli Sanchez


Whether you made eyes across the bar at the Beer Garden, “winked” at one another on OkCupid, or were set up by your friend who works in accounting, it’s time for the first date. First question on every girls’ mind –  what should I wear?

Don’t worry ladies, I’ve got you covered. Here is a quick guide that will ensure your look will get you a second date.

Plan the outfit in advance: Procrastination hardly ever pans out, especially when it comes to outfit selection. Pick your outfit out the night (or two) before so you don’t have the inevitable, “I have nothing to wear” whining session ten minutes before he is due at your door. No one likes that girl.

Check the weather: A girl should always be prepared for anything that might come her way. Don’t wear your best suede heels when there is rain in the forecast. It’s just not worth it. Be sensible, gals. If you aren’t sure about the weather, dress in layers so you aren’t sweating through the second course at dinner or shivering from the cold as he walks you home in the snow in your sweater set. I’m kidding…please don’t wear a sweater set.

Dress for the activity: If you’re going to be mostly outside, focus on a cute (and warm) jacket. Try to avoid those abominable snowman get-ups and go for a tailored jacket that defines your waist. Think about how much walking you might be doing and plan your shoe choices accordingly. You want to look great, but if you are limping from blisters or skating around in those heels, it could ruin your night. Be comfortable overall and pack a pair of flats in your bag just in case.

Add something that makes you feel special: It may be that you never feel fully polished without a mani or those new earrings you have been dying to wear. Do something for you that is extra special.

Here are a few easy, go-to outfit ideas to get you started:

  • Embrace the sweater weather. Try a chunky sweater with dark skinny jeans and boots (I’m a big fan of riding boots and they are great for walking). Remember when wearing skinny jeans that the top should be on the longer side. If the sweater you’re dying to wear is shorter, layer a longer tank under. The skinny jeans and boots are emphasizing your lower half, so go for a looser top. Accessorize, but don’t go wild. My rule of thumb is three pieces or less – and not all next to each other! Don’t wear the cocktail ring that could rival Princess Kate’s next to a chunky bracelet.
  • Dresses almost always look great. Try a slightly heavier fabric or a sweater dress. Don’t forget the tights! You could pair it with flats, but I think it looks great with boots! If it is a looser dress, try a belt to give yourself a waist. Consider wearing a vest over a dress to freshen up your look.
  • From the desk to dinner. Going straight from work? This can be tricky one especially if your office has a more formal dress code. Try a subtly patterned top (think small polka dots or lace) with a fitted skirt. Layer a fitted blazer over that you can take off later that night. You can never go wrong with a black and white ensemble, but remember to make it more interesting with a pattern and accessories.
  • And finally…don’t try too hard: I know this seems counter-intuitive considering you’re reading about how to be prepared for every possible outcome so this goes off without a hitch. But be yourself. Guys can tell if your hair took three hours – high maintenance alert.   Plus, you have better things to do. You should look like yourself, but with a little extra glow.

Alright, so I can’t guarantee that you’ll make a love connection or that he will look like his profile picture, but I can only do so much! Go get ’em ladies!



Cintli Sanchez is a Southie resident with a passion for fashion. By day, she works as a Project Manager in post-approval research.  By night, she enjoys organizing her friends’ closets, personal shopping, and spending time with her favorite accessory, Ruby the Cavapoo.