Summer Dates and How to Dress for Them

by Alison Jimenez, NYC Recessionista

It may be almost eight years since I went on my last first date, but the near-crippling indecision of what to wear on a date is still all too fresh in my mind. There are so many things going on in a woman’s mind when they’re trying to find that perfect date outfit, and so many variables to consider:

1. I want to look cute, but not like I’m trying to look cute.

2. What on earth do I wear to a baseball game?

3. How am I going to get on his motorcycle in a skirt?

4. If I wear this cocktail ring and he goes to hold my hand, will it be in the way?

5. I am always freezing at the movies, but I don’t want to wear too many layers.

If you’ve had thoughts like these before, then you know exactly what I am talking about. The problem is, we want our date night looks to be completely effortless. We don’t want to be seen tugging on our dress straps, fidgeting with our panty hose or pulling up our bras at any point during the evening; it ruins the illusion of perfection that we’re always trying to create (that is, until we’re on date four or five, and we can start to let little bits and pieces of our real selves show).

Well, now that summer is almost upon us, it’s time to start thinking about all of those great date nights that could be filling up your social calendars very soon. And in order to help put your date wardrobe fears to rest, I’ve put together some outfit ideas for several possible warm weather date scenarios.

For a Ballgame Date …

Just because you’re going on a sportier date doesn’t mean you can't wear a skirt or a dress. Just look for more athletic details and casual, laid-back pieces and you’ll definitely score big points.

1. TOMS classic canvas slip-ons from Nordstrom

2. Hive & Honey striped t-shirt dress from Piperlime

3. Indigo ink pocket tee from Madewell

4. Twill mini-skirt from Gap

5. Perth the Wait clutch from Modcloth

6. Nixon ‘Time Teller’ watch from Nordstrom

For a Beach Date …

If you’re headed for a date in the sand, I love the idea of a fun romper over your swimsuit. And going to the beach is the perfect excuse to break out a fabulous hat and cat eye sunglasses.

1. Long wrapped stone bauble necklace from LOFT

2. Lawn stripe sun hat from Ann Taylor

3. Twist bikini top and bottom from LOFT

4. Mint to Shine sandal from Modcloth

5. Woven web print drawstring romper from LOFT

6. A.J. Morgan Contessa cat eye sunglasses from Ruche

RELATED Sizzling Swimsuits Under $50 

For a Flea Market Date …

If you’re headed to a flea market on a date, then some whimsical pieces – think pastels, flowers, lace and polka dots – will be totally charming. Don’t forget a big enough handbag for your purchases.

1. Letting go crocheted top from Ruche

2. Sweetie polka dot chambray skirt from Ruche

3. Sketching Stories dress from Modcloth

4. Converse Chuck Taylor sneakers in paradise green from Nordstrom

5. Straw satchel from Gap

6.  The Pim + Larkin multi-colored drop earring from Piperlime

For an Outdoor Concert Date …

Outdoor concerts are a perfect chance to break out your more casual, bohemian pieces. I love the idea of a novelty print dress or an exotic print. And braided flat sandals are the perfect punctuation.

1. Seagull cove printed dress from Ruche

2. The Fossil vintage revival small flap purse from Piperlime

3. The Sabine cabochon chandelier earring from Piperlime

4. Weave Arrived sandal from Modcloth

5. Scenic view top in garden sketch from Madewell

6. 1969 legging skimmer jean from Gap

RELATED No Sweat! Bright Ideas for Melt-Proof Makeup

For a Dinner and a Movie date …

If I were headed to dinner and a movie, I’d want to make sure I wore pieces that were feminine, but simplistic. A hint of ruffle, or a tiny bit of sparkle, is just enough to make these pieces stand out.

1. The Anthropologie inked print top

2. Kaylan clutch from Banana Republic

3. Paloma & Ellie gold-tone hammered cuff from JCPenney

4. Eyelet cotton skirt from LOFT

5. Mm Couture visions of grandeur dress from Ruche

6. Step Into the Sunlight wedge from Modcloth

Above all else, make sure that 1) your outfit is appropriate for the activity, 2) that you’re comfortable in it, and 3) that it reflects who you are. Hopefully this post has given you some great ideas for what to wear on any date. And remember: the most important thing to wear on a date is a smile.

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About Alison, a.k.a. NYC Recessionista: Alison Jimenez is the sole creator and author of NYC Recessionista, a bargain shopping and fashion blog since 2008. Alison has an insatiable appetite for bargain shopping, mixing bargain basement and designer fashion in the same outfit, and getting more than one season's use out of her favorite pieces through the magic of mixing and matching. She also has a husband who would prefer it if she saved more than she shopped. In addition to her blog, Alison can be found on FacebookTwitterInstagram and Pinterest.

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