Going on a first date can be nerve-wracking for anyone. As a guy, you want to make a good first impression and look your best when meeting someone new. However, knowing what to wear on a date can be tricky. Should you wear a suit and tie or is that too formal? Would jeans send the wrong message? Ultimately, your date outfit should align with the plans for the evening and showcase your style and personality.
Consider the date details
The first step to determining your date night outfit is considering the details of the date itself. Where are you going? What time of day is it? Is it a casual coffee date or a dinner at an upscale restaurant? The venue and timing will dictate how formal you should dress for the occasion.
For daytime dates like meeting at a café or visiting a museum, casual attire like nice jeans or chinos paired with a button-down shirt or sweater is appropriate. Save the suit jackets and ties for evenings. For dinner dates, especially at nicer restaurants, pull out the sports coat and dress shoes. Select an outfit that is dressy but not over the top formal.
Think about what activities you may do and dress accordingly. If your date involves walking through a park or other active pursuits, go for stylish but comfortable shoes and clothing that allows movement. Make sure to check the weather forecast and bring layers if needed.
Dress appropriately for the location
In addition to the timing, the specific place you are going on a date matters for your outfit choice. A trendy café and upscale steakhouse have very different dress codes. You want to match the overall vibe of the venue.
Casual dates like coffee shops, diners, or low-key bars call for dark, neat jeans, casual button-downs or sweaters, and fashionable sneakers or boots. T-shirts and shorts are probably too laidback for a date, even during the day. Bring a blazer or sport coat if you want an extra layer for a polished touch.
For dinner dates at nice restaurants, step up into chinos or dress pants, a button-down shirt, sports coat or suit jacket, dress shoes, and potentially a tie. Make sure your clothes are neatly pressed – wrinkled dress clothes undermine the sharp look you are going for. Stick to darker neutrals like black, navy, or charcoal rather than bold patterns or colors.
Outdoor dates like concerts in the park or hiking offer flexibility. Go for stylish and functional outdoor wear like jeans, layered tee shirts, casual button-downs or sweaters, and weather-appropriate sneakers or boots.
Dress for your date plans
Consider the specific activities you have planned for your date when selecting an outfit. Your clothes should allow you to comfortably participate. For example, a suit or dress pants would be inappropriate for mini golf or an afternoon visiting an art museum and walking around town. Similarly, an elegant restaurant calls for more formal attire than grabbing a casual lunch.
Make sure your clothes fit your plans:
- Active dates like hiking, bowling, skating, etc. – wear athletic shoes, jeans or casual pants, tee shirt and/or casual button-down or sweater
- Casual lunch or coffee date – dark jeans or chinos, casual button-down, sweater or nice polo shirt, casual lace-up shoes or boots
- Museum, art gallery or downtown – dark fitted jeans, button-down shirt, casual sport coat or sweater, dress boots
- Upscale dinner – dress pants, collared dress shirt, tie, sports jacket or suit, dress shoes
- Concert or outdoor event – jeans, tee shirt, casual button-down, sweater, jacket if needed, sneakers or boots
Avoid overdressing for the occasion as that can come across as trying too hard. You want to look stylish but also relaxed and confident on your date.
Reflect your personal style
While you want to look polished and put-together for a date, your outfit should still reflect your personal taste and style. The right first date clothes allow you to feel like the best version of yourself, not like you are dressed up in someone else’s clothes.
Think about the colors, patterns, textures, and silhouettes you prefer when building your date night look. Work with pieces already in your closet that fit your style so you feel comfortable and confident.
Some style tips:
- Minimalists – stick to solid neutral colors like black, gray, navy or white and avoid bold prints or patterns
- Business casual – opt for dark wash jeans, pastel button-downs, sweater vests, and suede shoes
- Urban edge – try a bomber jacket, straight leg jeans, graphic tee and combat boots
- Preppy – wear chinos, an Oxford shirt, fun socks and loafers
- Rugged outdoorsy – layer a plaid flannel over a Henley tee, dark jeans and boots
The most important thing is that your clothes represent your vibe. You want your date to get to know the real you.
Pay attention to grooming and fit
To look your best for a date, all the details matter. From your haircut to your shoes, grooming and fit make a big impact.
Grooming
- Get a fresh haircut so your hairstyle looks neat and tidy
- Make sure facial hair like beards are trimmed and well-groomed
- Shower before the date and use deodorant and a subtle cologne if desired
- Brush your teeth and check for food in your teeth before leaving
- Clean and file nails if needed
Fit
- Select clothes that fit well through the shoulders, arms, chest, and legs
- Bring items to a tailor for slight adjustments if needed
- Avoid clothes that are too baggy, tight or short
- Make sure pants are the right length or hem them
- Wear clothes that are neat, not wrinkled, stained, or frayed
- Clean and polish shoes
Well-fitting, wrinkle-free clothes make you look polished. Pay attention to the little details that pull your date outfit together.
Layer for versatility
The weather, venue temperature, and activity can impact what you need to wear on a date. Dressing in layers allows you to adapt your look as required.
Some layering options:
- Button-down shirt under a sweater, cardigan or casual sport coat
- Tee or tank under an unbuttoned collared casual shirt or flannel
- Blazer on top of a sweater and collared shirt
- Bomber or Harrington jacket layered over a button-down or polo
- Vest paired with a dress shirt and suit jacket
Plan your layers so you can remove pieces if you get warm but have enough coverage for a chilly restaurant. Carry a compact foldable jacket that can fit in a bag or car.
Sample first date outfits
Not sure where to start? Here are some stylish date night outfit examples to inspire your look:
Casual coffee date
- Dark wash slim fit jeans
- Plain white tee or casual button-down shirt
- Bomber or Harrington jacket
- Fashionable lace-up boots or leather sneakers
Lunch date
- Khaki chinos
- Light blue Oxford shirt
- Navy cotton crewneck sweater
- Brown leather boots
Dinner at an upscale restaurant
- Navy suit and pants
- White dress shirt
- Slim dark tie
- Black leather dress shoes
Outdoor concert date
- Slim dark rinse jeans
- White or black tee shirt
- Neutral colored sneakers
- Black leather jacket
Use these looks as inspiration to create date outfits that align with the occasion and your personal style.
Essential items for your date wardrobe
Build up your date night wardrobe over time by acquiring versatile staples you can mix and match. Focus on purchasing quality pieces in materials like wool, cashmere, leather, and cotton that will last. Here are some essential items to have on hand:
| Date Wardrobe Essentials |
|---|
| Well-fitting jeans in dark rinse |
| Chinos in tan, navy or olive |
| Dress pants in black, gray, or navy |
| Button-down shirts in solids and subtle patterns |
| T-shirts and polo shirts in neutral colors |
| Crewneck sweaters in wool or cashmere |
| Sport coat or blazer in charcoal, navy or olive |
| Suit jacket/pants in navy or charcoal |
| Leather boots for casual dates |
| Leather dress shoes |
| Fashionable leather sneakers |
Build a collection of these wardrobe staples over time to create endless date outfits.
Conclusion
Figuring out what to wear on a date comes down to the details of your plans, dressing appropriately for the occasion, showcasing your style, and pulling the entire look together through fit and grooming. Be strategic about choosing items from your closet that are stylish but still comfortable so you feel confident on your date. The most attractive thing you can wear is your self-assurance as you focus on connecting with your date instead of your outfit.
