Dating After Divorce: Finding Your First Date Fit

A dating stylist expert shares her tips and tricks to building a confident dating wardrobe.
Six to Sunday

When Alyssa Dineen found herself back in the dating pool at the age of 41 after her divorce, she admits she was a bit naïve.

“I thought it was going to be awesome,” she says now, laughing. Fix-ups from friends never materialized, the phone didn’t magically ring, she didn’t just bump into Mr. Right while casually in line at Starbucks.

“Oh, the learning curve was steep,” she says. “I really started to think about how I was showing up in the world. I thought, maybe I’m sending out the wrong message?”

As a former fashion stylist who was pretty nimble when it came to clothes and photography, Dineen says she was able to “crack the code” in terms of what works when creating an online dating profile, meeting men, and dressing for a date.

Flash forward three years and Dineen has built an entire business on helping other women in the same situation. She offers tips, tricks, and private consultations, and last year she published a book that covers everything from developing the right frame of mind to building a dating wardrobe.

With Valentine’s Day upon us, we thought there was no better time to tap into Dineen’s expertise, just in time for a bit of romance.

Here's her advice.

Update Key Pieces

Updating four key pieces will make everything else you wear seem current. It’s important to wear what fits your body NOW, not what it WAS.

  1. Jeans: Find a jean style that works for you, and no more rules! If you like skinny jeans, wear them. If you prefer a wide leg, choose that.
  2. Eyewear: An outdated pair of eyeglasses ages you.
  3. A small evening bag: Get yourself a fun, little bag for going out (and leave your tote at home)!
  4. A blazer. Find one that’s not overly professional, as it is an ideal finishing touch.

You can’t go wrong with a classic fit, sculpting, skinny jean.

Eloquii Classic Fit Sculpting Skinny Jean

One of our favorite styles from the iconic CADDIS brand. Who wouldn’t want to support their slogan: “Get older. Own it. See stuff.”

CADDIS D28 Reading Glasses

Madewell bag. Large enough for the essentials, small enough to stow easily. This shape and style is a modern take (bonus: it can be worn as a cross-body).

Madewell The Piazza Mini Crossbody Bag

DKNY Blazer. Classic shape and style hat doesn’t scream “work” (that’s a good thing).

DKNY Double Breasted Blazer

Joe’s Jeans. High rise to keep everything pulled in and a full leg that gives trouser vibes. The dark rinse is flattering and can be dressed up.

Joe’s Jeans The Mia High Rise Wide Leg Jeans in Cinema

Refresh Your Skivvies

Those old, stretched, worn-out bras and panties are doing you no favors. Annnd it’s likely your body has changed, which means your size has likely changed. Get. What. Fits. And while you are at it, get yourself a few sexy pieces—a black bra and panty set, for instance--and make yourself feel good from the base layer out! Don’t forget to get one or two pieces of shapewear—they create a smooth foundation and give you confidence.

Soma Intimates are as functional as they are pretty. The bra has plenty of support, the bottoms provide the coverage you crave.

Soma Cotton Blend w/ Lace Hipster
Soma Unlined Lace Trim Plunge

Simple black lace is one of the sexiest in our books.

Intimissimi Pretty Flowers Cheeky Panties
Intimissimi Pretty Flower Elena Balconette Bra

This bodysuit does it all–tummy control, butt firms, and accommodates any neckline with its plunging bra.

Spanx Suit Your Fancy Plunge Low-Back Mid-Thigh Bodysuit

Choose Shoes Wisely

You don’t necessarily want to wear sensible shoes on a date, but you also don’t want to go so sexy so that you’re wobbling around or getting blisters. There’s nothing hot about wincing your way through an evening. Somewhere in the middle is best for first-date shoes. Fortunately, today’s heels have gotten a lot more comfortable, and a block heel at a reasonable height (2”) is ideal.

Sam Edelman. Silver is a neutral, and the bit of shine adds sex appeal.

Sam Edelman Terra Slingback Pump

Margaux bow mule. A flat that’s feminine but not sickly sweet.

Margaux The Mule

Margaux. Super comfortable and has the perfect heel height.

Margaux The City Sandal

Loeffler Randall block heel. Pumps are too profesh looking—here’s a comfy heel that, should the date go well, will ensure you can comfortably take a walk after dinner.

Loeffler Randall Dahlia Dark Gold Pleated Bow Heel

The “One Area” Rule

Show one area of skin— shoulders OR cleavage OR back. Not all of the above. Feeling good in what you’re wearing is sexy. For lots of women in our age group, our shoulders look great and an open neckline or off-the-shoulder top is great for evenings out. Just make sure you have the right undergarments so you don’t suffer the dreaded wardrobe malfunction.

1.State. It may still be sweater weather, but that doesn’t mean you have to bundle up.

1.State Cross Neck Cold Shoulder Cotton Blend Sweater

Free People. An off-the-shoulder style that can reveal one or both shoulders.

Free People We the Free Fuji Off the Shoulder Thermal Top

Zara blouse. Slightly sheer panels play the subtlest form of peek-a-boo.

Zara Mixed Vented Blouse

Astr the Label. Want something fitted and sexy? This is it.

Astr The Label One Shoulder Long Sleeve Rib Sweater

Favorite Daughter. Silky to the touch, plunging neckline, a bodysuit style that will stay put. Lots of colors to choose from.

Favorite Daughter Surplice Long Sleeve Satin Bodysuit

Limit Your Jewelry

Your accessories should not distract from your face or clothing. Dineen's advice? Pick one item as a stand-out—earrings OR necklace OR bracelets. Loading on the baubles is fun every once in a while, but for a first date, minimal is better. You want your date to be focused on you, not on the bling.

J.Crew Cocktail ring. When your approach to accessorizing is one-and-done.

J.Crew Square Crystal Cocktail Ring

Madewell necklace set. Necklace layering is very much on trend, this is how you do it.

Madewell Stone Collection Malachite and Freshwater Pearl Necklace Set

Alexis Bittar bracelet. A little bit edgy, a little bit sparkly, this strikes the perfect balance.

Alexis Bittar Crystal Studded Lucite Cuff Bracelet

Lizzie Fortunato earrings. Granny’s pearls? Frumpy. This is what’s current.

Lizzie Fortunato Stacked Pearl Earrings

Find Your First Date Uniform (FDU)

Finding your FDU will save you a lot of stress and running late for dates. Have your go-to dress or pants/top combo (including shoes and jewelry) that you know you feel great in. Our sniff test? You end the night feeling comfortable, confident, and having avoided any pulling or tugging!

Eloquii blouse. Sophisticated and feminine with just the right amount of skin.

Eloquii Satin Blouse with Ruffle

Wide-leg satin pants that are sexy enough for your First Fate Fit but also a perfect compliment to a well-rounded wardrobe.

Eloquii Wide Leg Satin Pant

Eloquii dress. Dressy enough for a date without screaming “trying too hard.”

Eloquii Satin Button Down Maxi Shirtdress

J. McLaughlin. One of the best-fitting, classic black pants we’ve come across.

J. McLaughlin Rylie Pants

Paige blouse. Designer-level details at a fraction of the price.

Paige Palma Pleated Ruffle Trim Silk Blouse

Reiss blouse. Just a pretty, cream top that you can pair with everything from jeans to trousers to joggers.

Reiss Brooklyn Sheer Sleeve Top

Michael Kors. Nothing beats a shirt dress in a print and color that can go with almost any accessory in your wardrobe.

MICHAEL Michael Kors Kate Micro Giraffe-Print Midi-Dress

Rails dress. Beautiful, feminine details in a neutral color.

Rails Cedra Dress

Brochu Walker dress. A splurge for quality and style - we especially like this hit of vegan leather and flattering (non-black, but still neutral) color.

Brochu Walker The Sky Belted Dress

About Alyssa Dineen:

Alyssa Dineen is a personal stylist and online dating coach based in New York City. Through her business, Style My Profile, she has successfully coached those looking to navigate online dating apps and put themselves out there with confidence. You can follow Dineen on Instagram, Facebook, Pinterest, and YouTube.


All products featured on Six to Sunday are independently selected by our editors and contributors. We may get paid commissions on products purchased through our links to retailer sites. However, we recommend products based on our independent research and point of view, and the decisions we make regarding the products we feature on our site are always driven by what we believe our community will love, first and foremost.

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