Gorgeous Looks for Romantic Milestones: A What to Wear SPECIAL!

As we embrace the month of February, we’re inspired by all of the love that’s in the air. Whether you’re single, dating or you’ve been married for 25 years, finding something in your closet for special occasions can be challenging. In this edition of What to Wear, we’re showing you beautiful styles to wear through every phase of a relationship from the first date, to meeting the parents to walking down the aisle. Even if you’re already married — who knows? Maybe your hubby will ask you to marry him all over again this Valentine’s Day!

Our models for this shoot are Thomas Walsh & Oksana Kusyo, who are engaged, and Kurt & Anissa Neubaur from The Olive Branch Foundation — all modeling at the breathtaking Hermitage Farm. The looks from Rodes For Him | For Her, Something Blue, Couture Closet and Clater Jewelers were created by our amazing stylist Shannon Kessler, with hair and makeup provided by her salon, Primp Style Lounge. (Plus we’ve got some fun stationery from Something Blue and a lovely wedding invitation suite from Etcetera.) Let’s start with the first date!

A Fun First Date Look

First dates are all about having fun! We recommend being comfortable yet polished. If you feel good in what you’re wearing, you’ll exude confidence, and your personality will shine through. Our stylist chose a cute, cozy top and jeans, then accessorized with a pop of color from the red sweater, a long necklace and fashion-forward snow boots.

Shannon’s style tip: First date jitters? Keep the worry at bay with this gray knit peplum top — a soft, romantic touch with a cute ruffle detail. We love this cranberry sweater that can be worn long or unzipped to make it hit at the hip.

From left to right: Thomas is wearing a Peter Millar shirt, $145; cream sweater, $650; and Joe’s Jeans, $168, from Rodes For Him | For Her. Oksana is wearing a grey ruffled top, $39; pink tassel necklace, $22; and red sweater with zipper detail, $66, from Something Blue, as well as Hudson jeans, $235, from Rodes.

These two are ready for a classic dinner-and-a-movie date or a night out on the town.

The first date is all about having fun!

A Sophisticated Look for a Special Night

For those who have been married for a few years — or maybe a lot of years — date night is especially cherished. Spice things up by getting extra fancy! These are chic looks — especially for an anniversary.

Shannon’s style tip: A leather pencil skirt looks great at any age and is perfect for just about any occasion. This beautiful winter-white silk blouse has a flirty lace trim that makes it ideal for date night. For the fellas, a pocket square with a sport coat is a chic way to keep it casual without overthinking it.

Anissa is wearing a white blouse, $305, and a leather skirt, $595, from Rodes For Him | For Her.

Kurt is wearing a blue Eton shirt, $265; Joe’s Jeans, $198; and olive plaid Byron coat, $795, from Rodes For Him | For Her, as well as a Seiko men’s solar watch, $235, and ArtCarved men’s 14K white gold wedding band, $1,099, from Clater Jewelers.

These two are ready for a fancy night out or an elegant anniversary dinner.

A Modest Look to Meet the Parents

When it comes to meeting his parents, a little black dress is always a classic choice. The first impression matters, so we recommend playing it safe but stylish. We love the floral pattern on this flattering knee-length dress — there are no worries of too much cleavage or not being able to bend over. This dress is, in a word, perfect!

Shannon’s style tip: Meeting the parents can be stressful. Being confident in how you look will help translate into a radiant first impression. This black sweater dress with floral side-panel detail creates a sophisticated yet relaxed ensemble. For the guys, dressing in business-casual is a great rule of thumb. Tuck in your shirt, opt for a dark denim and add a sport coat.

From left to right: Kurt is wearing a cream sweater, $650; Eton blue button-down, $265; and Joe’s Jeans, $198, from Rodes. Anissa is wearing Vince black pants, $995; a Vince top, $320; and an Eleventy blazer, $695, from Rodes. Thomas is wearing Joe’s Jeans, $168; a purple Eton button-down, $275; and navy Byron jacket, $595, from Rodes. Oksana is wearing a black sweater dress, $385; and carved bone and pearl bracelets, ranging from $90 to $115, from Rodes.

When meeting the parents, just relax and be yourself! We know they’ll love you.

We love this sweet card from Something Blue! It says, “Thank you for raising the man of my dreams.”

A small handbag is a great accessory for a dressy-casual outfit. Oksana is carrying a black Hammitt bag, $175, from Rodes.

And just when you thought you couldn’t love him any more, he pops the question! Oksana is wearing an ArtCarved diamond and rose gold semi-mount engagement ring, $2,195 + center diamond, from Clater Jewelers.

Fancy Looks for the Fellas

For the fellas, a classic button-down with a sport coat is always a great choice when you need to look sharp. For a particularly upscale event, we recommend slacks, but when it’s your family and friends, dark denim jeans will do just fine.

Left to right: Thomas is wearing Joe’s Jeans, $168; a purple Eton button-down, $275; and navy Byron jacket, $595, from Rodes. Kurt is wearing a blue Eton button-down, $265; Joe’s Jeans, $198; and olive plaid Byron coat, $795, from Rodes.

Kurt wears a dapper Seiko men’s solar watch, $235, and ArtCarved men’s 14K white gold wedding band, $1,099, from Clater Jewelers.

Up for a game of pool? Don’t mind if we do!

Goin’ to the Chapel …

When it comes to planning your wedding, keep in mind that your invitations communicate the expected dress code. Linda Humphrey, our etiquette expert from Etcetera, says, “Your invitations should drive what you want your guests to wear.” A fancy invitation will encourage your guests to dress elegantly, and a more casual invitation is perfect for relaxed, dressy-casual attire.

We love that this invitation from Etcetera looks like lace on a wedding dress!

These invitations are perfect for a formal, elegant wedding.

Wedding and Vow Renewal Gowns

Wedding dress shopping has to be, by far, the most exciting part of the wedding planning process. All four of these gowns are perfect for weddings and vow renewals. When it comes to choosing the perfect dress, it’s just like meeting your future husband: You’ll know when you find “the one” because it will make you feel like you’re the most beautiful woman in the world, and you’ll look back on your pictures with a radiant smile for years to come.

Look #1:

Oksana is wearing a stunning Ashley + Justin ivory lace gown, $1,650, from Couture Closet and a rose gold diamond drop necklace, $1,826, from Clater Jewelers.

A few last-minute touch-ups before the “I dos.”

Look #2:

Anissa is wearing a romantic off-the-shoulder Lillian West ivory lace gown, $1,530, from Couture Closet, and Galatea designer pearl, ruby and chrysoprase necklace, $1,065, from Clater Jewelers.

Pearl clutch, $85, from Something Blue | 14K yellow and white gold diamond bracelet, $3,749, and yellow and white diamond 18K white gold cluster ring, $1,920, from Clater Jewelers

The beautiful illusion back and scalloped, lace-trim train make this dress absolutely breathtaking.

Look #3:

Oksana is wearing a Blush by Hayley Paige ivory-and-cashmere sequin lace gown, $2,970, from Couture Closet.

The low back and dramatic train make this dress a showstopper!

Look #4:

Anissa is wearing a light gold-and-silver Lillian West flowy lace gown, $1,350, from Couture Closet.

This relaxed, flowy lace-top gown is so romantic and dreamy.

Happy Valentine’s Day! We hope you feel prepared for any romantic milestone that comes your way!

THANK YOU! THANK YOU! THANK YOU!

To our boutiques, Something Blue, Rodes For Him | For Her, Clater Jewelers, Couture Closet and Etcetera for providing the perfect looks and accessories.
To our photographer, Christine Mueller Photography, for shooting absolutely breathtaking photos.
To our stylist extraordinaire, Shannon Kessler, for making our models look incredible.
To Primp Style Lounge, for their impeccable hair and makeup services.
To Hermitage Farm for allowing us to use their stunning historic home and surrounding property.
And to Kurt & Anissa Neubaur of The Olive Branch Foundation, and Thomas Walsh & Oksana Kusyo for modeling for us.