You’ve matched, you’ve exchanged memes, you’ve typed “haha” so many times it’s lost all meaning… and now you’re actually going to see each other in person.
And suddenly the only thing in your head is:
“What do I wear so I don’t look weird, boring, or like a completely different person?”
Good news: you don’t need a new wardrobe or a new personality. You just need clothes that say, “Yes, this is the same person you liked online — just in higher resolution.”
Top dating website Dating.com prepared 7 very down-to-earth styling tips for both women and men to get you there.
1. Look like yourself, just slightly upgraded
If your friends wouldn’t recognise you, it’s the wrong outfit.
That’s the whole rule.
Skip the transformation fantasy and think: “What would I wear on a day when I want to look a bit extra good?”
If you’re a woman:
- Normally live in jeans and T-shirts? Keep that, but level it up: dark jeans, a nicer tee or tank, and a blazer or leather jacket.
- If you love dresses, pick one you can sit, eat, and walk in. A midi wrap dress or a simple slip dress with a jacket and low heels or flats is perfect.
- Zero ideas? Black top + straight or wide-leg jeans + ankle boots. Add earrings, done.
If you’re a man:
- Swap your hoodie for a good crewneck, polo, or lightweight knit.
- Choose dark, well-fitting jeans or chinos that don’t sag or strangle.
- Throw a casual shirt or overshirt over a tee. It instantly looks more “date” and less “just left the sofa.”
If you can look in the mirror and think, “Yeah, that’s me, just a better version,” you’re on the right track.
2. Dress for the actual plan, not some generic “date”
A 3 p.m. iced latte is not the same as a 9 p.m. rooftop cocktail, and your outfit should know the difference.
Before you decide what to wear, finish this sentence honestly:
“We’re meeting at a ___ and probably doing ___.”
Daytime coffee / park / museum:
- Women: jeans or tailored trousers, a nice top or knit, sneakers or ankle boots you can actually walk in, and a trench, denim, or bomber jacket.
- Men: chinos or clean jeans, T-shirt or henley, plus a bomber, overshirt, or denim jacket. Clean sneakers are absolutely fine.
Drinks or a relaxed dinner:
- Women: a midi skirt and top, or a simple black dress with a jacket and boots or low heels.
- Men: dark jeans or chinos, a shirt (Oxford, linen, or camp collar), maybe a lightweight blazer or cardigan.
Dressier restaurant or bar:
- Women: a slip dress with a blazer, or a tailored jumpsuit with heels or smart flats.
- Men: trousers or smart chinos, a crisp shirt, optional blazer, and loafers or leather lace-ups.
If you’d feel ridiculous standing in line for the bathroom next to everyone else, you’re probably overdressed.
3. Fit is always more attractive than whatever’s trending
Trends are fun. Fit is essential.
You can wear something simple and still look incredible if it sits right on your body.
Women, check:
- Shoulders of jackets and shirts: seam should land where your shoulder actually ends.
- Waist on dresses: should hit your waist, not your ribcage or your hips.
- Wide-leg trousers: they should just brush the top of your shoe, not mop the floor.
Men, check:
- Jeans/chinos: they should stay up without a belt and not cut into your stomach when you sit.
- Shirts: no buttons pulling across your chest, no “parachute” effect around your waist.
- Blazer (if you wear one): you should be able to button it and breathe like a normal person.
Do a quick test at home: sit, stand, walk, reach up. If you have to fix or adjust something every time, it will annoy you all night.
4. Let colour and texture do some of the talking
You don’t need a wild print to stand out. Small shifts in colour and fabric can change the whole mood.
For women:
- Neutrals like black, navy, cream, camel, and grey are always a safe, chic base.
- Add one romantic or tactile element: silk, satin, a soft knit, a hint of lace, good denim.
- Love colour? Pick one hero piece — a red top, an emerald dress, a cobalt blazer — and keep the rest calm.
For men:
- Try navy, olive, stone, or light grey instead of wearing head-to-toe black. They’re easier on the eyes and flatter more skin tones.
- Use texture: a knit sweater, suede or leather jacket, linen shirt, denim overshirt — all make simple outfits feel more intentional.
- If you want a colour pop, do it in your tee, shirt, or sneakers, not everywhere at once.
Think “interesting, approachable human,” not “walking billboard.”
5. Shoes and jackets: your silent first impression
People look at your face first. Then, without even thinking, they clock your shoes and outerwear.
For women:
- If you can’t walk a few blocks in them, they’re not first-date shoes. Go for ankle boots, loafers, ballet flats, heeled sandals with a stable heel, or clean sneakers.
- A good trench, blazer, leather jacket, or long coat can make even jeans and a tee feel like an outfit.
- Save the 12cm nightclub stilettos and micro-mini for a night that actually calls for it.
For men:
- Retire destroyed gym trainers for the evening. Minimal sneakers, Chelsea boots, desert boots, or loafers all work. The key word is clean.
- A bomber, denim jacket, Harrington, or relaxed blazer is often all you need to make a basic tee and jeans look intentional.
- If your shoes and jacket look chosen rather than random, you already look more put-together.
Quick check: if your date looked down at your shoes first thing, would you be fine with that? If not, change them.
6. The “little” details that matter more than you think
Once you leave the app and stand in front of someone, they notice the details: hair texture, nails, wrinkles in your shirt, how your clothes actually sit when you move.
Grooming basics for everyone:
- Hair doesn’t need a salon blowout, just some kind of order.
- Nails: clean. Polish is optional; “half-chipped from two weeks ago” is not the vibe.
- Beards: trim them on purpose or shave. The accidental-caveman look is… niche.
Accessories, if you’re a woman:
- One or two pieces of jewellery: small hoops, simple studs, a necklace, a ring. That’s enough.
- A structured bag (even a small crossbody) immediately makes your outfit look more intentional.
- Makeup doesn’t have to be heavy. Think: skin that looks like skin, a bit of definition, and either eyes or lips as the focus — not everything at full volume.
Accessories, if you’re a man:
- A watch, bracelet, or simple chain can break up the “T-shirt and jeans” thing in a good way.
- If you wear a belt, try to keep it vaguely in the same colour family as your shoes.
And scent:
- You want “come a little closer,” not “they’ll smell me before they see me.”
- One or two sprays is plenty. If you can still strongly smell it on yourself after a few minutes, dial it back next time.
7. If you can’t relax in it, don’t wear it
This might be the most important one.
If your outfit means you’re spending the whole night thinking about your outfit — sucking in your stomach, worrying a button will pop, tugging a skirt down every two steps — you’re going to feel stiff and distracted.
For women:
- You don’t need the tightest, shortest, or lowest-cut piece you own to look attractive. Confidence is much hotter than discomfort.
- Go with shapes you already know you like on yourself. That dress everyone compliments? Those jeans you always reach for? Start there.
- Put the whole outfit on the day before, take a quick mirror photo. If you’d send that pic to a friend without apologising for how you look, you’re fine.
For men:
- Don’t show up dressed as a Pinterest board version of yourself that has never existed. If you’ve never worn a blazer, maybe don’t combine blazer + loafers + tucked shirt for the first time on a first date.
- Build from clothes you actually like and feel comfortable in, then clean them up and upgrade a couple of pieces.
At the end of the day, the point isn’t for your date to fall in love with your jacket. The point is for them to feel like they’re finally meeting the person they’ve been talking to — and for you to feel relaxed enough in your own skin (and clothes) that they get to see the real you.
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