THE FIRST DATE? MAKE IMPRESSION WITH THESE MUST-HAVES

First date and first date look? First impression…  There is only one – make it amazing! It can be tough to know how much is too much when it comes to dressing up.  Our tips on a first date: the first thing to do is figure out where you’re going, because you really want to dress for the occasion. Say you’re going to the park: that sounds like jeans and sneakers, as opposed to if he was taking you to a really beautiful restaurant, that would be a silk blouse and heels. So that’s the first thing you want to determine. Then, the most important part is you want to wear something that makes you feel confident and beautiful, whether it’s your favourite pair of jeans and sneakers at the park, or a silk blouse, a pencil skirt, and heels at a beautiful restaurant. You really want to represent yourself in a true, real way. Don’t show up in a t-shirt and ripped jeans if you’re usually in feminine dresses and vice versa. First dates outfit is to be something that truly makes you feel like the best version of yourself. Because when you do that, you will have more confidence. And the more confidence you have, the more you will smile, the more you will engage and chances are, the more dates you’ll have!

 

 

*Click on the links under the images to buy online NOW!

 

 

1. Day Date

Balance gorgeous with casual to make both of you comfortable and smitten. A great rule of thumb for the first date: choose a colour or outfit that you are often complimented on. Comfort should be your first priority! The last thing you want to do is be fidgeting with your outfit – there are more important things to be thinking about!

Casual staples: jeans, converse or flats, t-shirts, and sunnies are great options for a casual daytime setting.

First Date2

1. Derek Lam 10 Crosby Long-Sleeve Striped Cotton Tie-Waist Shirtdress, Midnight/Soft White, $395.00. FREE SHIPPING + FREE RETURNS every day!

2. MICHAEL Michael Kors Fulton Tumbled Leather Moccasin, Light Sky, Original: $99.00, NOW: $69.00. FREE SHIPPING + FREE RETURNS every day!

3. Dior So Real Leather-Trim Metal Sunglasses, $825.00. FREE SHIPPING + FREE RETURNS every day!

4. Alexander Wang Lia Mini Soft Draped Shoulder Bag, Milk, $650.00. FREE SHIPPING + FREE RETURNS every day!

 

 

Let location be your guide – your look should reflect your environment! Also, pick one best asset to show off and that’s it. For example: do you have great arms? Wear a strapless maxi dress. Great legs? Wear shorts or a skirt. The bottom line – too much skin can actually be a turn off and look like you’re trying too hard.

Try just a simple white blouse and jeans for your next first date! Guys love a simple look, and it’s a lot less work for you!

First Date16

1. Lafayette 148 New York Leanne Pinstriped Blouse, $398.00. FREE SHIPPING + FREE RETURNS every day!

2. rag & bone/JEAN Dre Rolled-Cuff Skinny Jeans, The Pike, $225.00. FREE SHIPPING + FREE RETURNS every day!

3. kate spade new york metal-trim cat-eye sunglasses, $170.00. FREE SHIPPING + FREE RETURNS every day!

4. Gucci Carolina Suede Wedge Espadrille Sandal, Taupe, $595.00. FREE SHIPPING + FREE RETURNS every day!

5. Vince Signature V Croc-Embossed Baby Crossbody Bag, New Stone, $265.00. FREE SHIPPING + FREE RETURNS every day!

 

Don’t show too much skin! Avoid extremes like overly trendy outfits or heavy makeup. Natural and minimal is always best for the first date.

First Date4

1. Dior Chromic Square Acetate Sunglasses, $515.00FREE SHIPPING + FREE RETURNS every day!

2. Diane von Furstenberg Ivanka Embroidered Poplin Shirtdress, Deep Lichen, $368.00. FREE SHIPPING + FREE RETURNS every day!

3. Vix Woven Striped Beach Tote Bag, Black, $196.00. FREE SHIPPING + FREE RETURNS every day!

4. Gucci Carolina Suede Wedge Espadrille Sandal, Taupe, $595.00. FREE SHIPPING + FREE RETURNS every day!

 

 

An easy dress with some sort of jacket (depending on your style – a leather cropped bomber, a cardigan, a denim jacket, etc.) is always a great outfit combination. You can do flats or wedges depending on the setting and what you’re most comfortable in. The ultimate goal is to achieve the effortless “I just threw this on” vibe.

First Date3

1. A.L.C. Smith Long Wool Cardigan, White, $395.00FREE SHIPPING + FREE RETURNS every day!

2. A.L.C. Steele Passi Flora Silk Top, White/Multicolor, $295.00. FREE SHIPPING + FREE RETURNS every day!

3. A.L.C. Lucille High-Rise Grommet Shorts, Henna, $365.00. FREE SHIPPING + FREE RETURNS every day!

4. Rebecca Minkoff Isobel Leather Hobo Bag, Putty, $325.00. FREE SHIPPING + FREE RETURNS every day!

5. CoSTUME NATIONAL Pointed-Toe Wedge Mule, White, Original: $748.00, NOW: $561.00. FREE SHIPPING + FREE RETURNS every day!

 

If you wear something short, balance that out with long sleeves and a low heel. If you decide to wear something backless or low cut in the front, wear it with a maxi skirt or jeans.

First Date19

1. Helen Kaminski Kessy 10 Raffia Sun Hat, Natural/Black, $180.00. FREE SHIPPING + FREE RETURNS every day!

2. CoSTUME NATIONAL Platform Leather Sandal, Natural/Black, Original: $890.00, NOW: $667.00. FREE SHIPPING + FREE RETURNS every day!

3. T by Alexander Wang Long-Sleeve Knit Cutout Top, Black, $375.00. FREE SHIPPING + FREE RETURNS every day!

4. FRAME DENIM Le Skinny de Jeanne Ankle Jeans, Huntley, $219.00. FREE SHIPPING + FREE RETURNS every day!

5. Rag & Bone Enfield Mini Chain Shoulder Bag, Was $495.00, NOW $346.50

 

Wear something that fits you! It shouldn’t be too loose or oversized – something that shows off your figure but isn’t too tight.

First Date15

1. CoSTUME NATIONAL Lace-Up Striped-Flatform Oxford, Black, Original: $880.00, NOW: $589.00. FREE SHIPPING + FREE RETURNS every day!

2. Lafayette 148 New York 3/4-Sleeve Striped Jersey Tee, $248.00. FREE SHIPPING + FREE RETURNS every day!

3. Isabel Marant Etoile Flenn Tweed Double-Breasted Jacket, Midnight, $415.00. FREE SHIPPING + FREE RETURNS every day!

4. Marc by Marc Jacobs Leather Zip Satchel, $448.00.

5. Eileen Fisher Stretch Boyfriend Jeans, Faded Blue, $178.00. FREE SHIPPING + FREE RETURNS every day!

6. ABS by Allen Schwartz Jewelry Royal Flush Faceted Ear Jacket & Stud Earrings Set, $30.00

 

 

 

First Date13

1. MICHAEL Michael Kors Dottie Studded Leather Large Bucket Bag, Dove, $448.00. FREE SHIPPING + FREE RETURNS every day!

2. Nicholas Sleeveless Asymmetric-Hem Denim Dress, Blue, $375.00. FREE SHIPPING + FREE RETURNS every day!

3. Dior So Real Leather-Trim Metal Sunglasses, $825.00. FREE SHIPPING + FREE RETURNS every day!

4. Sophia Webster Lacey Lace-Up Gladiator Sandal, Blue, $695.00. FREE SHIPPING + FREE RETURNS every day!

 

 

First Date12

1. Tibi Chambray Off-the-Shoulder Mini Dress, Dark Denim, $345.00. FREE SHIPPING + FREE RETURNS every day!

2. CoSTUME NATIONAL Peep-Toe Flatform Slingback Leather Sandal, Black, Original: $950.00,   NOW: $475.00. FREE SHIPPING + FREE RETURNS every day!

3. ABS by Allen Schwartz Jewelry Royal Flush Starburst Faceted Drop Earrings, $45.00

4. MICHAEL Michael Kors Lena Large Leather Shoulder Bag, Black, $328.00. FREE SHIPPING + FREE RETURNS every day!

 

 

 

First Date11

1. Zadig & Voltaire Cotton Twill Snap-Front Jacket, Khaki, $495.00. FREE SHIPPING + FREE RETURNS every day!

2. Pedro Garcia Dorothy Platform Suede Sandal, Black, $475.00. FREE SHIPPING + FREE RETURNS every day!

3. Rebecca Taylor Cotton Lace-Trim Gauze Top, Snow, $250.00. FREE SHIPPING + FREE RETURNS every day!

4. MICHAEL Michael Kors Chelsey Convertible Leather Shoulder Bag, Black/White, $478.00. FREE SHIPPING + FREE RETURNS every day!

5. Current/Elliott The Cuffed Skinny Jeans, Armour, Original: $228.00, NOW: $159.00. FREE SHIPPING + FREE RETURNS every day!

 

 

First Date10

1. Alexis Hanne Off-the-Shoulder Poplin Top, White, $385.00. FREE SHIPPING + FREE RETURNS every day!

2. Melissa Odabash Straw Hat, $125.00

3. FRAME DENIM Le Bardot Striped Flare-Leg Jeans, Reeves, $239.00. FREE SHIPPING + FREE RETURNS every day!

4. kate spade new york fairmount square monday large striped crossbody bag, black/sandy beach, $178.00. FREE SHIPPING + FREE RETURNS every day!

5. CoSTUME NATIONAL Open-Toe T-Strap Leather Sandal, Black, Original: $830.00, NOW: $415.00. FREE SHIPPING + FREE RETURNS every day!

 

 

 

2. Evening Date

The reaction will tell you it was worth all prep.

Stand out on a more formal occasion by adding a statement piece of jewelry or a fun accessory as a conversation starter. Don’t be tempted to wear anything that you can’t walk in, eat in, or breathe in!

Don’t be afraid of prints when you’re going on a first date, especially if you love them. Don’t change what you love to wear because you think it will turn a guy off!

First Date7

1. Valentino Lacquered Rockstud Chunky-Heel Sandal, Coral/Army Avocado, $1,095.00. FREE SHIPPING + FREE RETURNS every day!

2. Rebecca Minkoff Suki Mini Leather Crossbody Saddle Bag, Poppy Red, $225.00. FREE SHIPPING + FREE RETURNS every day!

3. Alice + Olivia Tonya Silk-Blend Tie-Neck Blouse, White, $275.00. FREE SHIPPING + FREE RETURNS every day!

4. Alice + Olivia Sherri Floral Embroidered Shorts, Black/Multicolor, $348.00. FREE SHIPPING + FREE RETURNS every day!

5. Alice + Olivia Rory Floral Embroidered Jacket, Multicolor, $898.00. FREE SHIPPING + FREE RETURNS every day!

6. Marc by Marc Jacobs Magnetic Resin Cabochon Stud Earrings/Silvertone, Was $58.00, NOW $33.06

 

 

Comfort is key no matter what. If you feel good in what you’re wearing you’ll look good; confidence is everything. For a dressy dinner date, you’d go with a shift dress or skinny jeans, a silk camisole, blazer, and heels. For a casual dinner, boyfriend jeans and a cute blouse or tee are always a great bet.

First Date9

1. Theory Masibeth Continuous Wool-Blend Shorts, Gray Khaki, $265.00. FREE SHIPPING + FREE RETURNS every day!

2. Theory Sedeia Continuous Wool-Blend Vest, Gray Khaki, $485.00. FREE SHIPPING + FREE RETURNS every day!

3. Theory Jastrid Ruffled Silk Georgette Top, Dark Honey/Ivory, $255.00FREE SHIPPING + FREE RETURNS every day!

4. MICHAEL Michael Kors Pauline Patent Ballerina Flat, Light Blush, Original: $125.00, NOW: $87.00. FREE SHIPPING + FREE RETURNS every day!

5. 3.1 Phillip Lim Alix Flap Shoulder Bag, Fawn/Black, $1,095.00. FREE SHIPPING + FREE RETURNS every day!

 

 

Team your favourite shorts with a lace top. It’s romantic without being too formal.

First Date18

1.Majorica Callie 8MM White Pearl Threaded Drop Earrings, $65.00

2. Halston Heritage Marley Patent-Leather Sandal, Black Patent, Original: $395.00, NOW: $197.00. FREE SHIPPING + FREE RETURNS every day!

3.IRO Bridge Belted Leather Shorts, Black, $650.00. FREE SHIPPING + FREE RETURNS every day!

4. Rag & Bone Enfield Mini Crossbody Bag, $495.00

5. Self Portrait Sleeveless Textured Lace-Trim Top, White, $410.00. FREE SHIPPING + FREE RETURNS every day!

6. Bagatelle Pleated Front Leather Jacket, Original: $395.00, NOW: $197.00FREE SHIPPING + FREE RETURNS every day!

 

 

Maybe I’m just selfishly obsessed with this dress, but I think that the pinks and oranges are so fun and flirty, as is the style! It’d be perfect for a brunch date!

First Date20

1. Oscar de la Renta Short Beaded Silk Tassel Clip-On Earrings, $390.00

2. Pour la Victoire Camila Lace-Up Cage Sandal, Nude, Original: $265.00, NOW: $177.00. FREE SHIPPING + FREE RETURNS every day!

3. Alice + Olivia Electra Crepe One-Shoulder Shift Dress, Orange, $265.00. FREE SHIPPING + FREE RETURNS every day!

4. Yestadt Millinery Cheeky Straw Hat, Natural, $360.00. FREE SHIPPING + FREE RETURNS every day!

5. Rebecca Minkoff Suki Mini Leather Crossbody Saddle Bag, Poppy Red, $225.00. FREE SHIPPING + FREE RETURNS every day!

 

 

It’s hard to go wrong with a flirty dress on a first date. Too many to choose from? Decide what feature you want to highlight, and go from there! Try a sleeveless dress to show off toned arms or a mini if you love your legs. From there it’s all about accessories.

First Date21

1. Haute Hippie Sleeveless Floral-Embroidered Dress, Swan/Multi, Original: $495.00, NOW: $297.00. FREE SHIPPING + FREE RETURNS every day!

2. 3.1 Phillip Lim Martini Mid-Heel Leather Sandals, $450.00

3. 3.1 Phillip Lim Alix Flap Shoulder Bag, Fawn/Black, $1,095.00. FREE SHIPPING + FREE RETURNS every day!

4. Eddie Borgo 9MM Tan Mabé Pearl & Pavé Crystal Bracelet, Was $375.00, NOW $262.50

 

For a dinner date, go for a great pair of skinny pants that show off your figure (classic black leather or fitted jeans) with a nice silk tank or blouse and clutch. You can add a classic nude or black heel to dress up your look – a nice mix of dressy meets relaxed. For makeup, it’s all about the balance. Not too much, but not too little. You want to look like you put in the effort to look nice, but don’t want to over do it! You want to enhance your features, not overwhelm them.

First Date17

1. Elizabeth and James Cynnie Basket-Weave Mini Crossbody Bag, Dune, $495.00. FREE SHIPPING + FREE RETURNS every day!

2. MICHAEL Michael Kors Pierce Patent Cap-Toe Oxford, Black, Original: $150.00, NOW: $105.00. FREE SHIPPING + FREE RETURNS every day!

3. Neiman Marcus Perforated Suede Jacket, Original: $345.00, NOW: $120.00. FREE SHIPPING + FREE RETURNS every day!

4. Vince Layered Poplin Button-Down Shirt, $275.00. FREE SHIPPING + FREE RETURNS every day!

Vince Stretch-Suede Zipper Cuff Leggings, $945.00. FREE SHIPPING + FREE RETURNS every day!

5. MARC by Marc Jacobs Two-Tone Oversize Cat-Eye Sunglasses, Havana, Original: $130.00, NOW: $78.00. FREE SHIPPING + FREE RETURNS every day!

 

 

First Date23

1. MICHAEL Michael Kors Cynthia Large Evening Clutch Bag, Black, $198.00. FREE SHIPPING + FREE RETURNS every day!

2. Ralph Lauren  SWAROVSKI CRYSTAL EARRINGS, $600.00

3. Diane von Furstenberg Buckley Zip-Front Lamb Leather Jacket, Black, $998.00. FREE SHIPPING + FREE RETURNS every day!

4. Elizabeth and James Clarissa Sleeveless Party Dress, Black/Ivory, $365.00. FREE SHIPPING + FREE RETURNS every day!

5. CoSTUME NATIONAL Open-Toe Wedge Leather Sandal, Black, Original: $890.00, NOW: $445.00. FREE SHIPPING + FREE RETURNS every day!

 

 

 

First Date14

1. Vince Long-Sleeve Crossover Top, $225.00. FREE SHIPPING + FREE RETURNS every day!

2. MICHAEL Michael Kors Cynthia Saffiano Leather Shoulder Bag, Pale Gold, $248.00. FREE SHIPPING + FREE RETURNS every day!

3. kate spade new york becca jeweled t-strap ballerina flat, black/powder, $378.00. FREE SHIPPING + FREE RETURNS every day!

4. Current/Elliott The Stiletto Skinny Raw-Hem Jeans, Carlsbad Black, $228.00. FREE SHIPPING + FREE RETURNS every day!

5. Burberry Brit Ashurst Classic Modern Quilted Jacket, $595.00. FREE SHIPPING + FREE RETURNS every day!

6. Dior Chromic Square Acetate Sunglasses, $515.00FREE SHIPPING + FREE RETURNS every day!

 

For a mix of office appropriate meets date night, opt for a dress or skirt with a feminine top under a jacket. You can remove the jacket when you leave the office! Switch that big work bag to a clutch for an easy transition to evening.

First Date8

1. McQ Alexander McQueen V-Neck Combo Cardigan, Pale Gray, $425.00. FREE SHIPPING + FREE RETURNS every day!

2. Vince Vince Signature Collection Baby Crossbody Bag, $225.00

3. T by Alexander Wang Knit A-Line Skirt, Black, $235.00. FREE SHIPPING + FREE RETURNS every day!

4. Halston Heritage Marley Patent-Leather Sandal, Black Patent, Original: $395.00, NOW: $197.00. FREE SHIPPING + FREE RETURNS every day!

5. Kenneth Jay Lane Chunky Link Necklace/White, Was $90.00, NOW $63.00

 

 

Work attire is totally fine. A classic, fitted blazer is perfect for the occasion when worn the right way!

First Date1

1. Lauren Ralph Lauren FACETED TRIPLE-DROP EARRINGS, was $38.00 | NOW $14.99

2. The Row Smooth Leather Backpack 9, $2850.00

3. Veronica Beard Ruched Button-Front Shirtdress, Black, $495.00. FREE SHIPPING + FREE RETURNS every day!

4. CoSTUME NATIONAL Open-Toe Wedge Leather Sandal, Black, Original: $890.00, NOW: $445.00. FREE SHIPPING + FREE RETURNS every day!

 

 

First Date5

1. Diane von Furstenberg Blithe Silk Ruffle-Trim Tank, Black, $228.00. FREE SHIPPING + FREE RETURNS every day!

2. Diane von Furstenberg Nicola Wide-Leg Pants, Midnight, $368.00. FREE SHIPPING + FREE RETURNS every day!

3. Diane von Furstenberg 440 Gallery Leather Crossbody Bag, Was $298.00, NOW $208.60

4. Halston Heritage Anita Suede Strappy Sandal, Black, Original: $395.00, NOW: $201.00. FREE SHIPPING + FREE RETURNS every day!

5. ABS by Allen Schwartz Jewelry Royal Flush Starburst Faceted Drop Earrings, $45.00

 

 

 

First Date6

1. Kendall + Kylie Knot-Front Halter Top, Gingham, $98.00. FREE SHIPPING + FREE RETURNS every day!

2. Kendall + Kylie High-Waist Belted Cropped Trousers, Gingham, $148.00. FREE SHIPPING + FREE RETURNS every day!

3. Adriana Orsini Sterling Silver Round Framed Stud Earrings, $80.00

4. Pour la Victoire Shanna Crisscross Leather Sandal, Cream, Original: $195.00, NOW: $130.00. FREE SHIPPING + FREE RETURNS every day!

5. Rag & Bone Flap Crossbody Bag, Was $695.00, NOW $486.50

 

 

What are your tips for how to dress for the first date?

Thank you for reading my article! Please share it!

 

 

Leave a Reply

Your email address will not be published. Required fields are marked *

*