Let’s be real—figuring out what to wear on a date can be stressful. You stand in front of your closet, debating between “too fancy” and “too casual,” wondering if your outfit says fun and confident or just rolled out of bed. And that’s before the existential crisis of do I even own clothes that look good?
As a dating coach in Boston, I’ve seen firsthand how the right outfit can boost confidence and help set the tone for a great date. The key is simple: wear something that makes you feel comfortable, attractive, and authentic—without looking like you just threw on whatever was closest to your bed.
Professional Tips on What to Wear on a Date
So let’s break it down: what should you actually wear for different types of dates, and what should men and women keep in mind?
1. What to Wear on a Date: Keep the Occasion in Mind
The #1 rule: match the vibe of the date. Wearing the wrong outfit can send mixed signals—showing up in a tux for a casual coffee date feels like overkill, while gym clothes at a fancy restaurant might give the impression you don’t care.
Here are some foolproof outfit ideas for both men and women, based on the type of date:
Casual Coffee Lunch, or Dinner Date
These dates are laid-back, but that doesn’t mean you should roll in looking like you just got out of bed.
Men: A well-fitted t-shirt or polo with dark jeans or chinos. If it’s chilly, layer with a lightweight jacket. Clean sneakers or stylish casual shoes work best.
Women: A cute but effortless outfit like a casual dress, a nice blouse with jeans, or a stylish top with tailored pants. Small hill, flats, ankle boots, or even crisp white sneakers work well.
💡 Pro tip: Avoid wearing something brand-new if you haven’t tested it before. The last thing you need is realizing halfway through the date that your shirt is itchy or your jeans are cutting off circulation.
Fancy Dinner or Cocktail Date
Going somewhere upscale? Now's the moment to dress up and show that you put in effort.
Men: A well-fitted button-down shirt (or a dark, fitted turtleneck in winter) with dress pants. A blazer instantly adds sophistication. Leather shoes or stylish loafers complete the look.
Women: A flattering dress, chic jumpsuit, or a blouse with a sleek skirt or tailored pants. Heels or elegant flats work well.
💡 Pro tip: If you're unsure about the restaurant's dress code, err on the side of being slightly overdressed rather than underdressed.
Outdoor or Active Date (Walks, Picnics, Mini-Golf, etc.)
Comfort is key, but you still want to look put-together.
Men: A fitted athletic t-shirt or casual button-down with comfortable jeans or shorts. Sneakers or casual loafers work.
Women: Pants with a stylish top, a flowy sundress, or jeans with a cute blouse or sweater. Stick to comfortable shoes—think stylish sneakers or flats.
💡 Pro tip: Layering is your best friend. Bring a jacket or sweater so you’re prepared if the weather changes (and bonus: offering your jacket to your date is always a nice move).
Concert, Bar, or Night Out
These dates are all about fun and personality, so your outfit can reflect that!
Men: A stylish t-shirt or fitted button-down with dark jeans and boots or clean sneakers. A leather or denim jacket can add an edge.
Women: A trendy top with jeans, a fitted dress, or something bold and fun. Heels, stylish boots, or even statement sneakers work.
💡 Pro tip: If you're going dancing or standing for long periods, opt for comfortable shoes—you don’t want to spend the night complaining about your feet.
2. Prioritize Comfort Without Compromising Style
You know what’s attractive? Confidence—and nothing kills confidence faster than wearing something uncomfortable. If your outfit makes you feel awkward, stiff, or like you’re constantly adjusting it, it’s going to show.
Men: Make sure your clothes fit well—baggy shirts or pants that are too tight will make you look sloppy or uncomfortable.
Women: If you’re wearing heels, make sure you can actually walk in them! If you’re wearing a new outfit, test it out beforehand so you know it sits right when you move.
💡 Pro tip: If you don't know what to wear on a date schedule a consultation with a professional stylist.
3. The Little Details Matter
Your outfit is important, but so are the small things that make you look well put together.
Grooming: Fresh breath, neat hair, trimmed nails—these details don’t go unnoticed.
Shoes: Dirty, scuffed shoes can ruin an otherwise great outfit. Choose clean, stylish, and comfortable footwear.
Accessories: A well-placed watch, necklace, or stylish jacket can elevate a simple outfit without being over the top.
💡 Pro tip: A subtle, nice-smelling cologne or perfume can be the perfect finishing touch—just don’t overdo it!
4. Express Your Personality Through Your Outfit
Your clothes should reflect who you are, not just what’s trendy. For example, if you love classic styles, go for a polished and timeless look. If you’re into edgy fashion, rock a leather jacket or statement piece.
You should look like the best version of yourself. You want your date to get a glimpse of your personality from the moment they see you.
So What to Wear on a Date: Put On Confidence, Not Just Clothes
At the end of the day, what to wear on a date isn’t about following strict fashion rules—it’s about dressing in a way that makes you feel confident, attractive, and comfortable.
If dating feels overwhelming, reach out to a coach or professional stylist. As a relationship coach, I help clients succeed in dating (improve their confidence, make great first impressions, and finally figure out how to find love in a way that’s stress-free and fun).
So, next time you’re picking out an outfit for a date, remember:
✔️ Match the occasion
✔️ Prioritize comfort and confidence
✔️ Pay attention to the small details
✔️ Let your style show who you are
And if all else fails? Go with something clean, well-fitted, and effortlessly you. That’s always a winning look.
Special thanks to Style Fix Studio for the beautiful models and outfits.
Photography by Anna Morgan
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Anna Morgan Coaching specializes in guiding men and women in breaking through emotional barriers and developing the mindset and skills needed for successful dating. Anna offers 1:1 dating coaching for men, dating coaching for women, relationship coaching, and empowering dating profile pictures for successful online dating. Book a free discovery call and learn how your dating life can be changed.
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