Hello beautiful! I totally understand what you’re experiencing at the moment. You’ve got that wonderful first date ahead of you, and you’re standing in front of your closet looking absolutely bewildered. Trust me, I’ve been there far too many times to recount.

After all those years of fashion blogging and having heard from so many women about their dating experiences, I’ve figured out what actually works when it comes to first date dressing that turns guys on. Today, I’m spilling all my secrets.

First Date Outfit Guys Love Strategy

Preparing for a first date doesn’t have to make you anxious. The trick is finding that perfect balance between dressing incredibly well and also being yourself.

How to Dress with Confidence

Confidence is your ultimate accessory, ladies. I always tell my Style Up Ladies readers that if you feel confident in what you’re wearing, then you’ll exude confidence. Your confidence will dazzle brighter than any designer gown.

Choose clothes that make YOU feel fabulous first. If you’re always adjusting your outfit or dreading wardrobe malfunctions, your date will catch your angst.

Pick outfits you’ve worn previously and understand how to perform well on your physique. A first date isn’t the place to try out that new top you’re uncertain about.

Balancing Comfort and Attraction

The thing about first date clothes guys adore is that they’re not all about being beautiful. You must be comfortable enough to relax.

I learned the hard way when I wore killer heels to a walking date. Twenty minutes in, I was limping and wasn’t able to concentrate on the conversation.

Your dress should be suitable for whatever you’re doing. If you’re going out for coffee and a walk, don’t wear stilettos. If it’s a nice night out for dinner, don’t go in flip-flops.

What Color to Wear on a First Date Outfit Guys Love

Colors can either make or mar your first date appearance. From my experience, there are some colors that always attract great responses from men.

Red is a timeless favorite that shouts confidence and womanhood. It is bold without being overpowering. A red dress or a splash of red lipstick can be your magic trick.

Black is elegant and classic. It is particularly wonderful for night dates and makes you appear put-together without putting in too much effort.

Softer pastels such as blush pink or light blue emit sweet, friendly energy. These shades are perfect for daytime dates and brunch get-togethers.

Navy blue is business-like but feminine. It’s a conservative option that will fit nearly any date situation.

Stay away from neon shades or extremely flashy patterns on first dates. You need him to be concentrating on finding out about you – not distracted by your clothing.

Casual vs. Less-Casual First Date Outfit Guys Love

The secret to acing your first date wardrobe is matching the energy of your activities. Let me explain this for you.

Always check on the location of the date if you’re unsure. There is absolutely nothing wrong with asking “I want to dress for this – is it casual or dressy?”

If you’re unsure, you should dress up a little more than you believe is necessary. You’re better off being the best-dressed girl than risking being underdressed.

Casual First Date Outfit Guys Love

Casual does not equate to sloppy, ladies. Some of the most stunning first date styles are elegantly casual.

A playful sundress and sneakers or sandals are ideal for coffee dates or a lunch meetup. It’s comfortable, feminine, and demonstrates your thoughts about what you’re wearing.

Dark wash jeans with a good blouse provide a chic casual look. Top it with some adorable flats or low heels, and you’re all set.

A flowy midi skirt and a fitted top is the best balance. You’ll look perfectly put-together without going overboard.

For super relaxed dates such as hikes or park days, go with adorable athleisure. Consider matching gym sets in light-hued colors.

More-Dressed-Up First Date Outfit Guys Love

For dates that require dressing up, this is your moment to shine.

The little black dress is a classic for a reason. It is suitable for dinner dates, nights at the theater, or any formal dining establishment. Add heels and minimalist jewelry, and you’re golden.

A solid-colored midi dress with heels is an upscale look but not too formal. This is perfect for wine bars or nice restaurants.

Dress pants or a pencil skirt and a blouse project professional but feminine. This is great for workday dates.

Do not do full formal unless stated. Leave the floor-length gowns for real formal occasions, not for first dates.

Daytime vs. Evening First Date Outfit Guys Love

The hour of your date makes everything different in your outfit plan.

Daytime First Date Outfit Guys Love

Daytime dates require bright, natural styles that look good in natural lighting.

A sweet romper and sandals are ideal for brunch dates or outdoor adventures. Opt for a flattering shade that suits your skin tone.

Jeans paired with a nice blouse and ballet flats form a relaxed but polished day look. This is suitable for museum tours, shopping dates, or lunch dates.

A flowery dress and good footwear cries out daytime romance. It is ladylike, clean, and photo-ready for all those possible good Instagram shots.

Keep the makeup light for day dates. Consider natural radiant skin, mascara, and a nice lip color.

Evening First Date Outfit Guys Love

Evening dates allow you to turn up the glamour a little.

A wrap dress in a deep color such as burgundy or emerald makes for an evening look.

A silk blouse and dark jeans with heels accomplishes the perfect balance between dressy and casual for dinner dates.

A midi or a mini dress and heels is perfect for dinner dates or cocktails in the evening. Opt for deep colors or go for timeless black.

At night, when you can play up the dramatic makeup and jewelry. Go for smoky eyes, bright lipstick, or statement earrings.

Cool Weather First Date Outfits (Fall & Winter)

You don’t need to trade off style for comfort with cold weather.

Add an adorable sweater over a midi skirt with tights and boots. This adds texture and visual appeal while keeping you warm.

A sweater dress and knee-high boots are sexy and convenient for autumn dates. Get a fitted one that outlines your body.

For cold weather, attempt dark jeans with a cashmere sweater and an adorable jacket. Add ankle boots and you’re prepared for any winter date.

Don’t leave out a fashionable coat. He’s going to see your outerwear first, so make it memorable. A wool coat or adorable leather jacket can finish you off.

Warm Weather First Date Outfits (Spring & Summer)

Warm weather presents you with so many adorable outfit choices.

A flowy maxi dress with sandals is ideal for summer night dates. Pick one with a lovely print or in a solid color that suits you.

High-waisted shorts and a blouse tucked in make for an adorable, put-together summer outfit. Top with wedges or adorable sneakers depending on the activity.

Sundress and espadrilles is code for summer romance. The outfit is comfortable, feminine, and ideal for outdoor dates.

Do not forget sun protection. A cute hat or fashionable sunglasses can both be functional and trendy accessories.

Accessories to Wear on a First Date

The accessories can either save or ruin your first date outfit guys love.

Keep jewelry minimal but visible. A dainty necklace, small studs, or an adorable bracelet gives finishing touches without distracting from anything else.

Select a bag that complements your attire and date activities. A crossbody bag is excellent for action-packed dates, while a clutch suits dinner dates.

Your shoes must be comfortable enough to hold you out for the entire date. If you opt for heels, ensure you can actually walk with them confidently.

A light scarf will inject color and interest into plain clothes, and it’s useful in case the restaurant is chilly.

Steer clear of too flashy or noisy jewelry. You don’t want him to notice you flashing signals of attention, but rather looking at you.

Clothes to Avoid on a First Date

I’m going to save you from some big fashion faux pas that I’ve witnessed over the years.

Steer clear of something too provocative on a first date. Reserve the super low-cut top or very short skirt for when you’re getting to know one another better.

Wear shoes that are comfortable and won’t cause you to hobble through dates. I’ve seen too many women suffering through dates in agony inducing heels.

Avoid the new outfit you’ve never worn before. Opt for items that you know fit well and are comfortable in.

Steer clear of super trendy items that could date your pictures later. Timeless, classic items are always photogenic.

Do not dress like you’re heading to a club if you’re not, unless you are heading to a club. Reserve sequins and tight, body-hugging dresses for the right occasions.

First Date Outfit Guys Love: Dos and Don’ts

After speaking with hundreds of men regarding what they pay attention to on first dates, here is what I’ve discovered.

The Dos:

• Do dress in something that boosts your confidence. Your comfort level is apparent.
• Do wear clothes that are properly fitted. Well-fitted basics always appear more costly and polished.
• Do include one special detail in your outfit. Perhaps it’s a sweet necklace, nice shoes, or a bright lip color.
• Do take into account the date activity when dressing. Practicality is important.
• Do smell great. A light, pleasant scent is always welcome.

The Don’ts:

• Don’t try to be someone you’re not through your clothes. Authenticity is attractive.
• Don’t overdress or underdress for the occasion. When in doubt, ask about the dress code.
• Don’t wear anything that requires constant adjustment. You should be able to move naturally.
• Don’t choose an outfit that’s difficult to eat in if you’re going to dinner. Avoid white clothes for messy foods.
• Don’t forget to inspect yourself in varying light before you head out the door.

Final Thoughts: Selecting the First Date Outfit Guys Love

Here’s what I want you to remember above all: the ideal first date clothing is the type that makes YOU feel fantastic.

Sure, it’s good to know what men typically find beautiful. But ultimately, your personality and confidence are more important than any particular article of clothing.

Select clothing that is your style but suitable for the date. If you are more of a casual person, don’t try to put on an über formal outfit. If you enjoy dressing up, don’t have to dress down.

You want to look the best version of you. You want him to say “Wow, she looks amazing” but also “This is the real her.”

Remember, if he’s the right guy for you, he’ll appreciate your authentic style. And if he doesn’t? Well, then he’s not your person, and that’s okay too.

FAQs Regarding First Date Outfit Guys Love

What’s the biggest fashion error women make in picking first date outfit guys love? 

The biggest error is wearing something that’s totally out of their comfort zone. I see women attempting to be someone else through what they’re wearing, and it always fails because they’re not comfortable or confident.

Do I dress up more for an older man than a younger man? 

Not really age-wise, but think of his sense of style and the nature of the date. A man who is well-dressed himself will likely be glad when you dress up for him, whether he is older or younger.

Can I wear jeans on a first date? 

Yes! Dark, fitted jeans can look really sleek when worn with the proper top and accessories. It just depends on the location of the date and how you accessorize.

How much skin is too much on a first date? 

I abide by the “one area at a time” principle. If you’re revealing legs, top up. If you wish to reveal some décolletage, wear longer bottoms. It’s all about being tastefully attractive.

Do I get something new for a first date? 

Not a good idea. Wear something you already know will fit and that you feel good in. First dates are stressful enough without having to think about how your new clothes feel.

What if I’m not sure what the dress code is for the place of the date? 

Just ask! It’s completely okay to ask “I want to dress correctly – is it more dressy or casual?” Most of the guys will like it when you show respect for blending in.

Are sneakers okay to wear on a first date? 

Absolutely, as long as they’re suitable for the date activity and for your overall appearance. Clean and stylish sneakers may be fine for relaxed coffee dates or nature activities. Just ensure they’re well-conditioned.

What about dressing in all black – isn’t that boring? 

Black is never boring when it’s well-fitting! It’s classic and elegant. You can always introduce interest with texture, accessories, or a splash of color in your makeup or shoes.

Do I need to dress the same way for my first date that I do for my dating app photos? 

Your outfit should be consistent with your overall style from the photos. If all of your photos are of you wearing everyday clothes, don’t wear a cocktail dress unless the date is formal.

Conclusion

Finding the right first date outfit doesn’t have to be so difficult. The most beautiful thing you can wear is confidence in who you are.

Focus on clothes that fit well, match the date activity, and make you feel like the best version of yourself. Whether that’s a cute sundress, dark jeans with a pretty blouse, or a classic little black dress, the right choice is whatever makes YOU feel amazing.

At Style Up Ladies, we think that tremendous style begins with loving how you look in your own skin. So take these tips, make them your own personal style, and go crush that first date!

Your ideal first date attire is already hanging in your closet – you just need the courage to wear it. Now get out there and show him how great you are!