4 Dress to Impress Date Night Looks Sure to Get You Date No. 2

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First date: A nerve-wracking experience filled with awkward conversations and obsessing over the sounds you make when you chew. (Really, you don't do that, too? That's just us?) But beyond all those silent pauses, and the need to text all of your friends whenever he goes to the bathroom, is the first plight we are inevitably faced with: what to wear.

Now, your ideal date night outfit depends on where you two are going. Are you meeting at a park during the day, or is this a swanky restaurant-type of occasion? Is the first meeting going to be a fancy one, or are you keeping it casual? All of these things should factor in when choosing which pieces from your closet to put together. By the end of the night, even if the date didn't go well, at least you look amazing.

1. Cozy Casual
date night 6

If your date wants to enjoy the fall by going pumpkin picking or enjoying the changing leaves while walking through the park, then you're going to want to stay warm and keep your look casual. A dark sweater that shows a little shoulder ($29) placed over a maroon, suede skirt ($14) says you're both comfy and stylish. Peep toe booties ($51) are super in this season, and will look amazing with your laid back look, along with a cross body bag ($17) good for an on-the-go date. To accessorize, a simple, long necklace ($6) will compliment your understated, yet cute ensemble. And voila, you're looking fall fashionable!
2. All Dolled Up
Date night 3

If your new flame is truly a charmer, you may be going somewhere on the fancier side. For a first date to a sophisticated restaurant, or a play, it's time for some classic elegance. An off-the-shoulder crop top is always a sexy look ($8) but adding a pleated A-line skirt with a bow ($39) could make it more romantic. Bold red shoes with bows to match ($32) will give some color to your nighttime black and white. Finish it off with a long pearl necklace ($44) for a timeless piece, and a black buckle bag ($34) to hold your ticket, and you look like a stunner!

3. A Flirty Fling
date night 2
Maybe you're going out dancing, or your date is spontaneous and you don't know what the night holds for you! For a fun look that shows you're ready for anything there are only two options: Lace and leather. Try a lace crop top ($26) like this one with a burgandy leather pleated skirt ($21) for a new spin on a classic A-line. Pointed, strappy pumps in brown suede ($43) keep things funky, along with a statement, pendant necklace ($34). Show off your touches of style with a Bohemian purse ($29), and start your night off right.

4. Sassy Chic
Date night 5

If you're headed to that swanky new bar that just opened, or perusing an art gallery at night, you're going to want something structured but funky. A shoulderless dress in rose gray ($31), with a smooth leather jacket ($38) to go over it will have you looking ready for a night on the town. Adding bold berry booties with a chunky heel ($40) gives a potential daytime look even more nighttime appeal. Finish it with a fringe necklace ($35) and a black shoulder bag ($38), and you're equal parts sassy and chic.

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