Confidence on a first date begins with feeling good about what you’re wearing. Learn how to dress for different occasions.
What to wear
Trying to figure out what to wear on a first date? Regardless of your age, wear timeless clothes that fit you well. If you do this, you’ll look incredible.
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First dates are important, and you want to portray the best of yourself. You want to make a great impression and show that you put effort into getting ready for the date.
The key to dressing for a first date is to look effortlessly cool. This means that you look nice but natural.
Casual
The following are examples of what to wear on the first date in a casual setting:
Dark blue jeans and suede jacket
The items in the outfit are as follows:
- Jeans: Everlane The Slim 4-Way Stretch Organic Jean (opens in a new tab).
- Suede jacket: Reiss Jagger Green Suede Trucker Jacket (no longer available).
- Chukka boots: Johnston & Murphy ‘Copeland’ Suede Chukka Boot (opens in a new tab).
Denim on denim
The items in the outfit are as follows:
- Jeans: PAIGE Transcend – Lennox Slim Fit Jeans (opens in a new tab).
- T-shirt: Everlane The Cotton Crew T-Shirt (opens in a new tab).
- Denim jacket: Levi’s Denim Trucker Jacket (opens in a new tab).
- Sneakers: Nike Air Force 1 ’07 Sneaker (opens in a new tab).
Jeans and a t-shirt
The items in the outfit are as follows:
- Jeans: Allsaints Raveline Cigarette Skinny Fit Jeans (opens in a new tab).
- T-shirt: Everlane The Cotton Crew T-Shirt (opens in a new tab).
- Sneakers: Cole Haan GrandPro Low Top Sneaker (opens in a new tab).
Smart and business casual
The following are examples of smart casual first date outfits.
Jeans and a button-up
The items in the outfit are as follows:
- Jeans: Everlane The Slim 4-Way Stretch Organic Jean (opens in a new tab).
- Dress shirt: Eton Dark Red Zigzag King Twill Shirt (opens in a new tab).
- Loafers: Trask Sadler Loafer (opens in a new tab).
Chinos and sweater
The items in the outfit are as follows:
- Chinos: Bonobos Stretch Washed Chino 2.0
- Sweater: Nordstrom Cotton & Cashmere Crewneck Sweater (opens in a new tab).
- Boots: Magnanni Malone Chukka Boot (opens in a new tab).
Chinos and sportcoat
The items in the outfit are as follows:
- Chinos: Bonobos Stretch Washed Chinos (opens in a new tab).
- Dress shirt: Nordstrom Trim Fit Non-Iron Dress Shirt (opens in a new tab).
- Sport coat: Hart Schaffner Marx Wool Sport Coat (opens in a new tab).
Formal
The following are examples of formal first date outfits.
Blue suit
The items in the outfit are as follows:
- Suit: Boss Huge/Genius Trim Fit Solid Wool Suit (opens in a new tab).
- Dress shirt: Nordstrom Trim Fit Non-Iron Dress Shirt (opens in a new tab).
- Tie: The Tie Bar Mini Dots Wine Tie (opens in a new tab).
- Dress shoes: To Boot New York Brandon II Cap Toe Oxford
Charcoal grey suit
The items in the outfit are as follows:
- Suit: Hart Schaffner Marx New York Classic-Fit Solid Stretch Wool Suit (opens in a new tab).
- Dress shirt: Nordstrom Trim Fit Non-Iron Dress Shirt (opens in a new tab).
- Tie: Ermenegildo Zegna Silk Tie (opens in a new tab).
- Johnston & Murphy McClain Chelsea Boot
Black suit
The items in the outfit are as follows:
- Suit: Boss Huge/Genius Trim Fit Solid Wool Suit (opens in a new tab).
- Dress shirt: Nordstrom Trim Fit Non-Iron Dress Shirt (opens in a new tab).
- Tie: The Tie Bar Herringbone Black Tie (opens in a new tab).
- Dress shoes: Allen Edmonds Park Avenue Oxford (opens in a new tab).
First date tips
Now that you know what to wear on a first date, the following are 5 tips to help your first date go smoothly.
1. Safety first
Safety is always important, but especially if it’s with someone you haven’t met in person before or have only met once.
A great way to ensure your first date runs well is to have your first date in a public place with other people around.
2. Ask genuine questions
Conversations can begin with small talk but don’t let it stay there. If you continue to talk about the weather or what they ate today, chances are, you won’t feel a deeper connection.
Ask genuine questions to get to know the other person on a deeper level.
3. Be firm with boundaries
Everyone has personal boundaries and it’s important to maintain your boundaries.
You want to feel safe and respected while dating without any pressure to do something you don’t want to do.
This also goes for the other person, you should respect their personal boundaries,
4. Know what you want and need
What do you want from a person? What’s your intention with dating?
Yes, you want to make a great impression, but you also want to make sure the person is a good fit for what you want.
You may need to go on more than one date to figure this out but don’t let a good impression cause you to be someone you’re not.
5. Enjoy the moment
A first date can be stressful and that makes it easy to forget to be present. Being nervous, worried about what you’re wearing or what the other person thinks is normal.
Overcome those thoughts with a reminder to enjoy the moment and have fun. Even if it doesn’t work out, by having a good time, it’ll be worth it.
Conclusion
By knowing what to wear on a first date, you can now focus on preparing for the date. Enjoy the moments, be present, keep boundaries, and have fun.
Featured photo by David Em/Next Level Gents.