Belle,

Getting dressed for Valentine’s Day last night left me with a horrible realization. I only have one date night dress. I have plenty of work dresses that I adore, cocktail dresses that are woefully underworn, teeny dresses for bars/going out, and sundresses that would do fine for a date in the summer. But a flattering dress less conservative than a work dress, more casual than a cocktail dress, and less i-can’t-breathe-or-eat than a going out dress?

I have one: a black 3/4 length sleeve, mini a-line skirt, jersey dress. And its boring. Help!

Kara

You would think that finding a date dress that allows you to breathe and eat comfortably wouldn’t be a difficult undertaking, but too often, you would be wrong.  I think easy dresses in simple shapes that can be accessorized with one or two items are probably what you’re looking to buy.  And when it comes to dates, there are several looks you can go for, but I think we’ll focus on three: relaxed chic, pretty/flirty and a bit sexy.

 Dress: Trina Turk Sculptor Dress ($288)

Top: Sam Edelman Abbott Sandal ($130) // Resin Statement Necklace ($36) // Nine West Club Clutch ($50)

Bottom: Rachel Zoe Gladys Sandal ($235) // Karen London Wave Bangle ($120) // Anya Hindmarch Newman Clutch ($325)

Shift dresses that hit mid-thigh are great for evenings out.  First off, they flatter a lot of body types and give you room to breathe and eat without feeling like a prisoner of your own clothing.  Secondly, you can dress them up or down depending on the occasion.

For the first outfit, I added a sexy high heel, a chunky necklace and simple gold clutch.  I’d wear the hair down and a slightly bronzy-beachy makeup.  You could also wear the hair up, lose the necklace and add some big earrings.  I also like the idea of wearing these chunky, horsebit-detail sandals with it and a more relaxed clutch like this one.

The second outfit strikes me as the perfect thing for dinner when you’re on vacation.  A cool flat sandal (similar for less), an awesome wood bangle (similar for less) and a crazy cool bag in another color.

Yes, the fringe on the bag is extreme, but sometimes it’s fun to do something less serious.  If you’re not down with it, try this green foldover clutch instead.

Dress: Eliza J Fit and Flare Dress ($138)

Accessories: Majorca Hammered Gold Earrings ($105) // Rebecca Minkoff Honey Clutch ($395) // Naturalizer Prissy Sandal ($50)

This look is going to be too conservative for some of you, but bear with me for a minute.  I love the way a pleated chiffon skirt floats and moves, I think it’s so feminine and pretty.  And I think this dress could be a very versatile addition to a woman’s wardrobe, so while it’s a more conservative choice, if you style it right, I think you get a really flirty/pretty look.

If that’s not what you’re going for, do as a friend of mine suggested and get a leather jacket and a studded black heel and go the other direction.

Dress:  Open Back Midi-Dress ($59)

Accessories: Cluster Earrings ($19) // Alexander McQueen Knuckle Clutch ($1,095) // Zara Strappy Heel ($90)

Over the last few years, all I’ve thought about is my career.  So all of thought about is clothes for my career.  As a result, it’s been difficult to remold my thinking to allow space for sexier date clothes.  I’ve always had a more demure sense of style, so I’ve been trying to find ways to be sexy without feeling uncomfortable.

I immediately latched onto this open back dress from ASOS because it has some drama, but I’d still feel like me in it.  I also like this embellished white one, this bright blue one and this snug-fitting lace mini.

For the accessories, I wanted to do something different so I selected a knuckle clutch and some high sandals.  For the money, I think Zara has the most stylish shoes I’ve seen.  They’re modern and unique and they usually cost under-$150.  And if you’re looking for a similar clutch at less-than-McQueen prices, I LOVE this BCBG one.

So how do you ladies like to dress for dates?  Especially dates that aren’t casual but aren’t cocktail either?