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What to Wear on a First Date: Five Tips for Dating Bliss

Your personal style speaks loudly—or softly, depending on who you are. The first thing you want to wear is confidence. Whether a date is a total bore or romantic revelry, being confident is attractive and helps you feel good. Start with being comfortable and finish with the right reflection of your personal quirks. Wear something you think is cute. 

That said, we can all polish our presentation with a little good advice. Here are 5 tips on what to wear on a first date. And, remember, have fun! You said yes for a reason. 

Tip 1: Dressed Up or Casual Dining, Be Comfortably Cute 

Let your date know who you are. We all strive for a relationship that is fun, comfortable, and every day. So, whether wearing a little black dress for a fancy evening out or going for coffee—be comfortable.

First Date Outfit No-No’s and Yes-yesses

    Breaking the ice is not the time to break in those new 4-inch heels. You do not want to be thinking about your painful feet instead of your charm. If you’re wearing jeans, consider the walk-anywhere comfort of a decorated boot or mule or more-casual heel. In the summer, sandals, flats and espadrilles signal sunshine and brunches.

    Are those new shoes a must-wear? Take some time to break them in a few days before.

    No too-tight skirts and shoes you can’t walk normally in. Clothing that inhibits spontaneity can limit where your date leads—or when it ends. Wear something—whether a skirt, dress, or pants—that can casually extend a date. Leave room for a romantic walk or bouncing between places.

    Prepare for the unexpected. The right layers allow for cold spells and overactive ACs. Have easy-to-carry layers for longer-than-expected outings.

    Bigger bags help hold light sweaters or cardigans. Think about including tights, a hat, or a pair of gloves. Accessorizing with scarves and shawls also helps extend an evening. Think about handbags with an accommodating central compartment, like bucket or hobo bags.

    Be an all-weather wonder. If it’s wet or hot out, choose sweat-proof makeup and pinned up hairstyles. Prepare for rain with a water-resistant handbag and super cute umbrella. Sunglasses for lunch dates make for great invitations to sit outside or wait for a sunset. 

Tip 2: Pack for Powerful Attention

    Pay attention to your date, not your wardrobe. Avoid looks that aren’t within your comfort zone or require a lot of upkeep. Unless your date is taking you to the Oscars, your red-carpet look may be a black mark.

    Be prepared without the baggage. Your bag should be consistent with your date. Keep your makeup routine easy to quickly perk up with a subtle (and quick) trip to the bathroom. Don’t take the biggest bag you have—unless you need it. Think about the outing. Botanical gardens, boardwalks, or day trips can be great for stylish backpacks. If you are heading to a show that may require standing or small, theater-like seats then take a clutch, wallet with strap, or small handbag.

    For smaller bags, consider stocking makeup samples rather than a full-scale makeup bag.

Bonus tip: Ask your date about them. And pay attention to what he asks about you. Getting to know each other means there should be room for both of you. 

Tip 3: Timing is Everything with Date Outfits 

What to wear on a first date really depends on timing—from dressy dinner dresses to cute lunch date outfits. 

First Date Dresses – Day or Night

The little black dress is a classic for a reason. Keep a few convertible first date dresses that can be accessorized to spruce up or dress down depending on those last-minute decisions—like what restaurant to meet at. 

Your day-to-night, casual-to-dressy date dress doesn’t have to actually be black. Consider any solid-color dress to accessorize. A red halter dress, for example, can work with natural makeup, sunglasses, scarves, and sandals to create a great daytime look. Try adding a bold custom Christo bracelet and necklace to make a statement. Trade bold bangles for more delicate or sparkly jewelry, high heels, and upswept hair for dinner dates. 

Dress Jeans is a Real Thing

Your mother’s ideas of cute first date outfits are as contemporary as corsages. By the time you say “yes”, you probably know something about your date. A casual person isn’t likely looking for a disco diva. Your urban-sleek is probably not down with a yoga pants and fro-yo date. Consider the date—and why you thought you’d have fun with them. Dress accordingly.

Denim can go everywhere. Women’s jeans are now designed for any kind of look. Darker, sleek jeans (usually a little form-fitting) and heels are sexy and chic. 

Express Yourself

Charm bracelets and personalized bags can say a lot about who you are. Maybe it’s your dog and not your diamond that is your best friend. Travel bug looking for a cuddle bug? Brighton charms are dazzling ways to start a conversation. Customize your look with colorful bracelets, necklaces, and earrings.

Tip 4: Is it the Right fit? Dress for Your Body Type

Everyone has a different body type. Embrace its beauty. Be your best apple-, pear-, hourglass-, or straight-shaped body. Generally, avoid unkempt looks. Your clothes should fit you—physically and otherwise. Avoid adopting looks that only look good on someone else. Don’t try and squeeze into unflattering fits. 

Below is a brief overview of dressing for you.

What is Your Body Shape? The four main body shapes—and what to wear! 

There are four main body types: apple, pear, hourglass, and straight. If you are unsure what you are, the best date dresses for all body types are A-lines. Pick a solid color for the most flattering look and personalize it with your statement pieces.


What is an Apple Body Shape? 

Apple body types carry most of their curves on the top without being curvy through the hips or backside. Your waistline is not, however, very well defined. And that’s totally okay!


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Dress for an Apple Shape

The comfiest tops also showcase your beautiful bests! A+ for A-lines. Summer peasant and Boho blouses, tunics, and button ups are brilliant on you. V-necks are virtually made for you. Scoops and v-necks draw attention to and elongate the neck. Sturdier fabrics for seeking out the flowy freedom of the traditional comfy cuts.

If you are looking for more formal, pick an empire waisted dress or wrap dress. And, the apple body is the best shape for popular strapless and maxi dresses. Apples often have legs they love, so don’t be shy about short hemlines.

Avoid belts, high-waisted pants, pleated fronts, and anything double breasted. Staying away from things that puff up around the mid-section (like puffy sweatshirts) or finish at the waist is probably not ideal. Also, chunky puffy boots and things that shorten those slimmer legs are total faux paus. 

Accessorize Apple!

While boasting your bustline, choose accessories like longer pendant necklaces paired with bolder bracelets that show off your length and frame your upper body. Especially if you have short hair, be bold with earrings. Avoid belts that draw the eye down. 

Handbags that hit just above-the-hip or long and subtle below keep their eyes upward. However, avoid bags that end just at the bust. If you have a little extra around the middle, avoid handbags that hang right at the middle and crossbody bags.


What is a Pear Body Shape? 

Call it pear, spoon, or whatever you like. The pear-shaped body tends to have hips and waists that are proportionately a little lusher than your shoulders, arms, and chest. Hippy can be just as sexy as anything!  

Dress that Perfect Pear Shape

The main fashion challenge for the pear-shaped woman is creating balance between your upper and lower body. Patterns, statement tops and accessories, and dramatizing your tops all help bring balance to your overall look. 

Big bonuses for great necklines. Go for plunging scoop or v-necks, cowls, or bold cut-outs. Sleeves are another sensational secret weapon. Look for bell sleeves, puff sleeves, serious shoulder embellishments, and blazers and jackets with structured shoulders. Stick with jackets that cut in at the waist. 

On the bottom, stick with darker, non-patterned pants. Boot-cuts and slight bells can bring balance. Avoid pegged pants and boxy cut bottoms. For skirt length, stick to skirts that hit just below the knee (or longer) to lengthen your look.

For date-time dresses, look for A-line cuts and empire waists. Show off those shoulders, back, and neck with plunging lines, backless dresses, cut-outs, and belted styles.

Accessories for Perfecting Pear Shapes

Pear with lots of accessories. Draw attention upward with earrings, bolder necklaces, bright scarves, and hats. Belts—especially on playful, flowy maxis or A-line dresses—are a great way to draw out curves and emphasize your smaller waistline.


What is an Hourglass Body Shape? 

Hourglass is the typical iconic bombshell—think Marilyn Monroe. Your dimensions are fairly even with a smaller, defined waist cinching under a larger chest and above curvy hips. Your hips and bust are fairly even. This doesn’t mean that you are built for just-any-dress success. A lot of clothing is designed for fashion models, who are more v-shaped.

Dress for an hourglass shape

Too often, clothing is not made for your bodacious beauty. The trick to showing off your proportions is to emphasize your waist and curves. Fitted and tailored looks are great for hourglasses. 

On top, don fabulously fitted jersey tees, wrap tops, and lower necklines. Avoid baggy tops like peasant blouses. Draw eyes to waistlines with jackets that have defined waistlines or end fitted at the waist—like bomber jackets. 

Date dresses do really well to play up your curves. Wrap dresses, fitted-then-flare cuts, side-cinched dresses, and fitted color-block dresses all give pop to proportions.

Pants will depend more on your height and weight for hourglass shapes. Whatever rise you like, emphasize curves fitted skinny jeans and downplay curves with bootcut legs. Avoid cropped lengths and boxy jeans that bag near the ankles. 

Empty your closet of all things boxy. That’s the major no-no.

Accessorize the Hourglass

You want to stay as balanced as your curves. Bring it all together with a thin belt—a shiny embellishment totally okay. And stay away from overly structured handbags. You have a curvy appeal. Keep it consistent with soft, low structured bags. Hobo bags and bucket handbags are often soft.


What is a Straight or Athletic Body Shape? 

You are straight as a ruler. Even if you aren’t athletic, people sometimes assume you are. This is called the rule-, banana-, athletic-, rectangle-, or straight- body shape. Hips and shoulders are about the same and your body’s weight distributes pretty evenly—whatever BMI you are. And no matter how thin you get, you aren’t going to have that hourglass waist. Inverted triangle body types are usually between this body type and an apple.

Dress for an Athletic Shape

You can create shape with your straight body type. If you are a little heavier, pick a favorite area to play up. Love your shoulders, go for halter tops or bare-shoulders. You can borrow from all the other shapes to emphasize what you like—creating a waist with structured tops and bigger belts, for example. To minimize size, pick A-lines. If you are athletic, play up your arms and back.

In dresses, slip dresses and streamlined looks play off the straight lines of the athletic build. Long lines aren’t broken by hips and other curves. If you like your bust, plunge necks or empire waists are jaw droppers. 

Athletic Body Accessories

You can play freely. If you love your arms, pair rings and bracelets with sleeveless or cap sleeved tops. Long pendants can play up the muscular chest and collar bones. If boasting a flat belly, a blingy belt on low-waisted jeans will showcase your fitness. Really, play with what you like. Satchels, crossbody handbags, and backpacks can play up that look of life on the go. But if the bag is too structureless, it may leave you looking a little flat. 

Tip 5: Accessories Speak Volumes

Handbags and jewelry say something about who you are and are great conversation starters. No, most people do not actually want to talk about fashion. But, that ring you bought on vacation can be a place to launch conversation into travel aspirations. Are you someone a little edgy? That rockstar bag (like one from our Pretty Tough Collection) may help bring attention to your boldness. Casual girl? How about that straw handbag or playful tote?

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