What to Wear When You Haven't Dated in Years | Three Date Night Outfits

What to Wear When You Haven’t Dated in Years

Dating Outfits For Women Over 40

I’ve gotten a lot of questions recently about what to wear if you’re a woman over 40 and getting back into the dating game (after a long hiatus). That is SO scary!! The dating rules have changed. You are much older. What the heck do you wear?? You want to be modest, but still, look and feel sexy!

I’ll walk you through three different dating scenarios below and explain why I chose and styled each date night outfit. You can easily recreate these looks. I promise!

And these outfits are perfect even if you’re not back on the singles dating scene. You can wear these date night outfits with your hubby, boyfriend or partner.

Date Night Outfits for when you havent been on a date in a long time, date night look for women over 40 jeans pumps blazer

Date Night Outfits for when you havent been on a date in a long time, date night look for women over 40 jeans pumps blazer

date night outfit for women over 40 years old that are new to the dating world, what to wear when you havent dated in years

date night outfit for women over 40 years old that are new to the dating world, what to wear when you havent dated in years

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classic heeled black pumps perfect for date night outfit for women over 40, what to wear when you havent dated in years

date night outfit blazer and leather pants for women over 40 years old that are new to the dating world, what to wear when you havent dated in years

date night outfit blazer and leather pants for women over 40 years old that are new to the dating world, what to wear when you havent dated in years

CAMI | PANTS | BLAZER | DICKEY | NECKLACE | HEELS | SUNGLASSES | BAG | BELT

Date #1 | Blazer & Coated Jeans for a Great First Impression Outfit

You are meeting for your very first date! It’s exciting and terrifying at the same time. You want to look sophisticated, but you also want to look sexy – striking a balance between the two can be tricky. On your first date, I think you should stay pretty comfortable and covered. I would suggest wearing your signature look with a few minor tweaks.

I am wearing my favorite Veronica Beard blazer with some edgy twists. In this look, I am comfortable, covered and warm. There isn’t a ton of skin showing. You won’t look desperate… and you don’t look like you are trying too hard. BUT… you don’t look frumpy either because of the sexy touches.  Let me walk you through those strategic add-ons!

First, the silky, lace cami definitely adds a touch of femininity and sexiness. Next, I added a super sexy choker necklace (sold out, but linked a similar option). Third, the pants are leather by Rag & Bone. They are luxe-looking and sophisticated, but again edgy and sexy. (For more affordable pants that also come in petite, make sure you check out this post.) And lastly, the heels! These are three-inchers by Ann Taylor. (Note that as the dates progress, my heels get higher! ;))

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado

TOP | SIMILAR JEANS | BOOTS | SUNGLASSES | BAG | BELT

Date #2 | All About the Curves For the Follow-Up Date

Okay, so you like each other! The first date was successful and you’re thinking… let’s give this another shot to see if it has legs. Whelp, for this special occasion, you are going to create some super sexy curves! The most feminine and coveted body shape is an hourglass. I for one do NOT have that shape. I’m a straight-up box! But, with some styling magic… I can create the illusion of curves for days.

Here is the secret formula:

First, you find a top or blouse with a shoulder building detail. This top by IRO is definitely one of my favorite finds of the season. It has a sexy, flattering, plunging neckline. It shows just the right amount of skin. I tucked the blouse into some super high rise, ripped skinny jeans by Rag & Bone. These are sold out but I linked similar ones! The jeans have to be high rise to make this work… again to highlight your waist and shape. The skinny jeans also hug and exaggerate curves. Then I threw on some sexy croc-embossed boots by Schutz. I mean…woah. These boots are everything! But the key to this curvy look is the waist-defining belt! Voila… you’ve got curves!

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado

TOP | SIMILAR JEANS | HEELS | BAG | SUNGLASSES

Date #3 | You’re Hitting it Off – Show Some Skin!

Alright, alright, alright… date #3! Now, we mean business! For this important evening, you want to show some strategic skin. Don’t overdo it. Just a little shoulder or some leg…whatever makes you feel the most comfortable and confident. A fail-safe option is a subtle shoulder-baring top like the one I’m wearing above. Isn’t this top SO good?? It’s by Nanushka and I am in love with it! It’s HOT… but still sophisticated.  I paired the top with some minimally distressed, dark gray skinny jeans and finished off the look with some slightly higher heels! These pumps by Jimmy Choo are around 4 inches high. 

Please let us know how your second foray into the dating world is going in the comments below. Did you try one of these looks?? Did you create your own super hot and sophisticated look?? Please share all the details so we can learn from your experiences.

Thank you so much and good luck!!

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