Picking an outfit for a first date can be tricky, especially if it’s a casual daytime date where you want to look nice but not overdressed. The key is finding the right balance that shows you put in some effort but are still relaxed and comfortable. For a casual first date, aim for casual-chic – think smart casual pieces that are stylish but not too dressy. Here are some tips on how to dress for a casual first date:
Consider the activity/location
The first thing to think about is where you’ll be going and what you’ll be doing. This will give you an idea of the appropriate attire. For example:
- Coffee date – Jeans or casual pants with a nice top and jacket/cardigan are perfect
- Lunch – Sundress or dark jeans with a blouse and wedges/booties
- Mini golf or arcade – Dark skinny jeans, t-shirt, and sneakers
- Museum – Slacks or a knee-length skirt with a blouse and loafers
Dress for mobility if there will be a lot of walking or activity. And consider layers in case the temperature changes.
Stay casual and comfortable
While you want to look nice and put-together, you also want to be comfortable on a first date so you can focus on your time together rather than your outfit. Stick to casual fabrics like denim, cotton, jersey knits in styles you feel good in.
Some go-to items for a casual date include:
- Dark, indigo wash jeans – jeans are a casual date staple, just opt for a dark pair without rips or distressing
- Leggings with a tunic or long sweater/cardigan
- Casual sundress or romper
- Skirt with a casual blouse or sweater
- Dark wash jean shorts in warm weather
- Cotton shorts and a relaxed button-down or peasant top
The key is looking put-together but not overdressed. Stay away from items like old sweatpants, revealing crops tops, and anything too dressy.
Pick flattering, figure-hugging pieces
While comfort is key, you also want to look and feel your best on a first date. Look for pieces that are flattering for your figure rather than boxy and shapeless. For example:
- Stretchy dark jeans that hug your curves
- A blouse that cinches at the waist
- A lightweight sweater dress that skims your body
- Leggings that accentuate your legs
Flattering details like v-necks, wrap styles, and belted waists can show off your shape in a subtle way.
Accessorize minimally
Accessories are great for personalizing an outfit, just keep them minimal for a daytime date. A few tasteful accents are perfect:
- Small delicate necklace or chain
- Simple bracelet or watch
- Small earrings or hoops
- Casual hat for outdoor dates
- Crossbody purse or tote bag
Limit loud statement pieces and costume jewelry. And only wear 1-2 statement accessories at a time so they don’t compete. For example, bold earrings and a necklace may be overkill.
Pick shoes you can walk in
Since many first dates involve walking, choosing comfortable versatile shoes is a must. Skip the sky-high stilettos and opt for:
- Flats, loafers, oxfords
- Low wedges or heels
- Booties with walkable heels
- Sandals
- Nice white sneakers
Bring a cute pair that transitions from day to night in case you continue the date. Breaking them in before the date helps.
Don’t overdo hair and makeup
You want your hair and makeup to look natural but enhanced for a day date. Go easy on the products, colors, and textures.
Some tips:
- Soft, touchable curls or a sleek blowout
- Neutral smokey eye and pink lip gloss
- Groomed brows and mascara
- Minimal foundation to even out skin tone
- Soft pink or peachy blush
- Beach waves with texture spray
The focus should be on looking polished but not overstyled. And of course, only wear as much as you feel comfortable in.
Check the weather
Since dates may involve walking between places, check the weather and prepare accordingly. Some tips:
- Bring layers like a denim or leather jacket to add or remove
- Carry a compact umbrella or rain jacket if rain is expected
- Wear sunscreen if it’ll be hot and sunny
- Bring a pashmina or scarf to wrap up if cold
- Check the forecast morning of to confirm your outfit
Being prepared for the weather will allow you to focus on enjoying the date.
Do a mirror check
Before heading out, do a quick mirror check to make sure you look neat, styled, and photo-ready. Look for:
- Flyaways, lint, strings? Smooth them down
- Smudged makeup? Clean it up
- Untucked tags or buttons? Tuck and button
- Crooked necklace? Straighten accessories
- Anything stuck in teeth? Check smile
It’s important to look polished from head to toe. Turn and check from all angles in the mirror. Taking an outfit photo can help spot issues too.
Sample Outfit Ideas
Here are some example first date outfit combinations for different date scenarios:
| Date Scenario | Outfit Idea |
|---|---|
| Lunch Date | Wrap dress with flats or wedges and light cardigan. Simple jewelry and bag. Natural makeup with tinted lip balm. |
| Casual Dinner | Dark skinny jeans, heeled booties, silk tank or blouse, leather jacket, necklace. Medium makeup with red lipstick. |
| Active Date (hiking, mini golf) | Leggings or athletic shorts, moisture-wicking top, crossbody bag, and sneakers. Ponytail and light makeup. |
| Museum Date | Slacks or knee-length skirt, blouse, flats, crossbody bag. Simple jewelry and makeup. |
These are just a few ideas to give you inspiration on styling casual date attire. The most important tip is to dress like an elevated version of your everyday self – stylish pieces you love but feel relaxed and confident in.
Additional Tips
Here are some final tips for dressing for a casual first date:
- Pick an outfit that flatters your body type.
- Make sure clothes are wrinkle-free and fresh.
- Have date-ready outfits planned out or laid out in advance.
- Bring breath mints, lip balm, and any other touch-up items.
- Spritz on perfume or body mist for a nice scent.
- Shower, shave, and groom yourself neat and tidy.
- Exude confidence in how you carry yourself.
At the end of the day, the right first date outfit is one you feel amazing wearing. So opt for pieces you love that express your personal style. Focus on fabric, fit, and flattering silhouettes. And consider the date activity when deciding what level of casual dress is appropriate. With the right casual-chic outfit, you’ll look stylish and feel comfortable to enjoy your time getting to know each other.
Conclusion
Dressing for a casual first date is about balancing looking stylish and put-together with remaining comfortable and relaxed. Consider the date details like activity, location, and weather to determine the appropriate level of casualness. Choose flattering, casual pieces in materials like denim, cotton, and jersey. Minimal accessories and natural makeup also keep the look day-appropriate. Stay true to your personal style and opt for outfits that make you feel confident, cute, and authentic to yourself. With the right casual date attire, you can focus on having fun and making a genuine connection.
