Whether to dress up or go casual for a first date is a common dilemma. You want to look and feel your best, but you also don’t want to come off as trying too hard. The key is striking the right balance between looking put-together yet relaxed. Ultimately, how casual you can dress depends on the type of date – an upscale restaurant calls for more formal attire than meeting at a cafe. However, some general guidelines apply.
Consider the date location
The location of your date provides clues about how casual or formal you should dress. An upscale restaurant, theater performance, or cocktail lounge call for dressier attire – think cocktail dresses, button-downs, blazers, trousers, and dress shoes. More casual venues like coffee shops, casual or ethnic restaurants, mini golf, or museums allow for more relaxed outfits. Think dark jeans, nice tops or sweaters, flats or boots. Outdoor dates tend to be more laid-back as well.
Know your date interest
Think about your date’s interests and personality type, which offer hints about their style. If they’re into hiking, volunteering, or the arts, they likely appreciate casual, comfortable style. A career-focused date who works in law, business, medicine, or academia may lean toward more formal looks. Check their social media for style clues too. Ultimately you want an outfit that reflects your personality while respecting their preferences.
Consider your personal style
Don’t compromise your own style too much. If you feel most confident in jeans and casual tops, stick to a polished version of that. If you love wearing dresses and heels, go for it. The key is looking like the best version of yourself. For women, dark skinny jeans, knee-high boots, and a silky cami can look just as chic as a dress while still being casual. For men, dark fitted jeans, dress shoes, and an ironed button-down is sharper than sloppy jeans and a tee.
Pick the right fabrics and fit
Fabric choice and fit make all the difference in looking polished yet casual. Stick to high-quality fabrics like denim, leather, and knit sweaters. Avoid overly revealing, sloppy, or wrinkled clothing. Make sure jeans and tops fit well – not too tight or baggy. These small details elevate casual pieces into first date worthy outfits.
Accessorize thoughtfully
Jewelry, bags, shoes, and other accessories complete your outfit. Bold jewelry and an elegant bag glam up casual basics. Mens accessories like watches, dress shoes, and belts add polish. Stay away from over accessorizing or pieces that are damaged, overly casual, or distracting. You want accessories that pull your look together.
Allow room for venue changes
Your date may start at one location and move to another with a different vibe. Coffee dates may transition to a walk in the park or drinks at a bar. Dinner reservations may lead to a chic lounge for cocktails. Allow room in your outfit for venue changes by keeping pieces versatile. Layers like blazers, cardigans, and scarves easily dress up casual basics for evening.
Dress for confidence
Most importantly, wear something you feel great in. Your confidence matters more than sticking to arbitrary fashion “rules.” Don’t wear anything too outside your comfort zone or requiring constant adjustment. Choose fabrics, silhouettes, and styles you know complement you. A confident, authentic look allows your personality to shine through.
Sample Outfits
| Date Type | Women’s Outfit | Men’s Outfit |
|---|---|---|
| Casual lunch or coffee date | Dark skinny jeans, oversized sweater, ankle boots, crossbody bag | Dark fitted jeans, casual button-down, loafers |
| Museum or park stroll | Printed skirt, tucked-in top, denim jacket, flats | Chinos, sweater over collared shirt, casual sneakers |
| Dinner at an ethnic restaurant | Faux leather leggings, drapey blouse, wedge booties, statement necklace | Dark jeans, knit sport coat, dress boots |
| Trendy cocktail lounge | Bodycon midi dress, moto jacket, strappy heels, clutch | Slim trousers, button-down, Chelsea boots |
Guidelines for Women
- Dark, fitted jeans or leather leggings are safe casual options.
- Elevate outfits with knit blazers, moto jackets, or draped cardigans.
- Slouchy sweaters and soft blouses balance fitted bottoms.
- Ankle boots, ballet flats, and chic sneakers are casual yet polished shoes.
- A crossbody bag adds practicality while keeping hands free.
- Simple gold or silver jewelry polishes the look.
- Stay away from cutoffs, shorts, sweatpants, hoodies, revealing tops, and flip flops.
- Stick to one focal statement piece like bold jewelry or an edgy jacket.
Guidelines for Men
- Dark denim and chinos are versatile bottoms.
- Button-downs, polos, and sweaters work for casual dates.
- Blazers, sports coats and fitted knits add polish.
- Loafers, boots, and sleek sneakers are good shoe options.
- A watch and simple leather belt make nice finishing touches.
- Avoid shorts, sleeveless shirts, sweatpants, athletic sneakers, and sandals.
- Stay away from more than one statement piece or anything loud.
Conclusion
Asking how casual you can dress for a first date is common. The location, your date’s style, your own comfort level, and plans for the date dictate the outfit formality. However, dark denim, knits, button-downs, blazers, and sleek shoes form safe options for both genders to strike that balance between polished and relaxed. Remember to dress in a way that makes you feel confident, stay true to your personal style, and keep pieces versatile for any venue changes. With thoughtfulness and care, you can craft first date outfits that show your date you respect their time while allowing your awesome personality to shine through.
