Dating over 40 comes with its own set of perks: more confidence, fewer games, better wine. But what to wear on a first date? That’s where things can get unnecessarily complicated. You don’t want to look like you’re trying too hard. But you also don’t want to look like you didn’t try at all.
Fashion advice tends to ignore people dating later in life and most outfit ideas lean too trendy, too young and too out-of-touch with real wardrobes. The good news? You just need to know what works for your age, your body and your personality without sacrificing comfort or good taste.
This guide breaks down the best first date outfits. No fast fashion. Just smart, stylish picks from Lands’ End that fit your life and your date.
What to Wear on a First Date
First dates always come with a little buzz of uncertainty. Where to go, what to say and of course, what to wear. First date outfits set the tone before the conversation even starts, and the right one makes everything else feel easier. Here’s how to strike the balance between relaxed and refined with date night outfits for women and men.
For Women
The goal isn’t to dress younger. It’s to dress better. Think effortless polish, pieces that look intentional but not overthought. A soft blouse with subtle detailing, crisp cotton that doesn’t wrinkle mid-dinner and a flattering dress you can move in. Keep it simple. Skip anything fussy or clingy. If you’re adjusting your outfit more than your napkin, it’s not the right fit.
Layer with purpose. A lightweight cardigan, tailored blazer or longline sweater adds structure without trying too hard. And if you’re going with denim, make it count: dark washes, quality fabric, clean lines. Pair it with block heels or wedges you can walk in and one piece of jewelry that doesn’t beg for compliments but gets them anyway.
For Men
No one expects a three-piece suit, but a casual buttondown that holds its shape past the first drink? That matters. A classic oxford or No Iron shirt says you respect the evening without overplaying it. Skip the loud logos and golf shirts. Go for texture: chambray, brushed twill—something with personality that doesn’t read as trend-chasing.
Pants should fit, not squeeze, not sag. Chinos or dark men’s jeans work across the board if they’re clean and well-cut. And yes, grooming counts. Even the sharpest outfit can’t fix an “I forgot we had plans” face. Keep it sharp. Keep it easy. Keep it you.
Dressing for a Date Over 40 Can Look Youthful, Yet Sophisticated
Dating at this stage doesn’t mean toning it down. It means tuning it right. You know your style, you know your pace and odds are you know what you’re looking for. That makes choosing first date outfits easier, if you stick to pieces that reflect your personality, fit well and don’t fight for attention. Whether it’s your first-first date or your first night out in a long while, here’s how to keep your look sharp, confident and date-ready.
For Women:
- Blouses with shape: Go for buttondowns that give a little at the waist or drape without clinging. Feminine without trying too hard.
- Structured layers: A refined cardigan or soft blazer adds polish without being stiff.
- Dark denim or dress pants: Skip anything overly distressed. A clean bootcut or tapered leg does more with less.
- Chic flats or low heels: Prioritize comfort, but not at the expense of style. Think sleek loafers or a block heel in a neutral.
- Minimal accessories: One statement piece, a bold earring or a textured cuff, is more than enough.
For Men:
- No Iron buttondowns: They stay crisp all evening and don’t need a second thought.
- Well-fitted khakis or jeans: Go dark, skip anything baggy or too slim. The right fit matters.
- Casual jackets: A chore coat, knit blazer or lightweight field jacket adds dimension without being too formal.
- Clean, classic shoes: Desert boots, loafers or minimalist sneakers keep things grounded.
- Skip the graphic tees: Stick with simple crewnecks or henleys if you’re layering under something.
When in doubt, remember: date night outfits in your 40s don’t need reinvention. They just need a little intention.
Dating at 50 Blends Maturity with Generational Style
Style in your 50s comes with one major advantage: perspective. You’ve seen the trends come and go. You’ve figured out what feels good and what doesn’t deserve space in your closet. When it comes to date night outfits, the goal isn’t reinvention; it’s refinement.
This is about looking like yourself, just on a really good day. Whether it’s a casual coffee or dinner somewhere with mood lighting, you don’t need loud patterns or risky silhouettes to make an impression. You just need smart layers, clean lines and pieces that move with you.
For Women:
- Soft knits with shape: Try a lightweight cardigan sweater or turtleneck paired with a midi skirt or polished pants.
- Tailored bottoms: Choose ankle pants, straight-leg jeans and a structured skirt, achieving comfort and confidence in equal measure.
- Statement jackets: A utility jacket, denim layer or classic trench gives the outfit a focal point.
- Heeled boots or smart flats: Comfort counts, but the shape matters, too. Pointed toes or sleek soles go a long way.
- Accessories that work overtime: A scarf in a modern print or a standout bag adds texture without bulk.
For Men:
- Collared knits or polos: They bridge the gap between dressed-up and laid-back, perfect for dinner or drinks.
- Well-made jeans or chinos: Avoid any stretch-heavy fabric. Look for weight, durability and a straight-leg fit.
- Jackets with character: A canvas shirt-jacket, lightweight quilted coat or corduroy overshirt adds warmth and style.
- Neutral-toned shoes: If you want to keep things simple, stick with brown or tan leather. Black works, too; just skip anything shiny.
- Watch or leather band accessory: Not required, but it’s a sharp finishing touch that quietly says you’ve thought this through.
If you’re dating over 50, style doesn’t mean chasing trends. It’s about finding a first date outfit that speaks up without shouting.
Tell a Refined, Yet Playful Story When Dating at 60
Dating in your 60s doesn’t come with a dress code, but it does deserve more than your usual Tuesday outfit. You’ve got taste, you’ve got stories and you know the difference between clothes that behave and ones that betray you after an hour. For your date night, what to wear doesn’t have to be complicated. Stick to smart staples, nothing stiff, nothing loud, just well-made pieces that do exactly what you need them to.
For Women:
- A-line or midi dresses: These give you movement, shape and polish with no tugging or second-guessing.
- Drape-friendly cardigans or wraps: Light layers add elegance and practicality without adding bulk.
- Refined flats or wedges: You want something that adds finish without adding stress to your knees or feet.
- Subtle sparkle: Think gold hoops, a sleek pendant or a bold cuff, just one. It’s about balance, not flash.
For Men:
- Buttondowns that hold up: Go with No Iron or brushed cotton. Roll the sleeves if it’s casual; tuck it in if it’s not.
- Layering pieces with shape: A lightweight sweater, shirt-jacket or knit zip-up adds structure without effort.
- Solid, reliable pants: Chinos or straight-leg jeans with enough weight to hold their own and enough stretch to sit comfortably through dinner.
- Classic shoes with tread: Loafers, brogues and leather sneakers that don’t look orthopedic but still feel supportive.
- A belt that matches your shoes: It’s a small thing, but it makes everything look pulled together.
Over 60, your outfit doesn’t need to overcompensate. Whether it’s your first date in years or just your first one this week, Lands’ End makes it easy to look like you’ve had style all along. Because you have.
Frequently Asked Questions
Every first impression counts, but that doesn’t mean you need to overthink what to wear on a first date. These quick answers help cover the details we haven’t already nailed down.
Should I dress differently for a daytime date vs. an evening date?
Yes, but not dramatically. For daytime, lean toward lighter fabrics, relaxed silhouettes and comfortable shoes; for evening, add structure, deeper colors and slightly more polished footwear.
Can I wear denim on a first date?
Absolutely, as long as it's the right denim. Clean, well-fitted jeans in a dark or mid-tone wash can look sharp when paired with a tailored top or crisp button-down.
How do I dress for a casual date without looking underdressed?
It's all about balance. Pair something easy (like a cotton tee or knit top) with something tailored (like chinos or a blazer), so the outfit feels relaxed but still intentional.
Find First Date Outfits That Flatter Your Finest Features
Dressing for a date at any age doesn’t have to feel challenging. Whether you’re just breaking into middle age, or nearing retirement and a slower pace, the right outfit isn’t about reinvention. First date outfits are about leaning into what already works and wearing it with intention.
It all comes down to smart, reliable pieces that look good without trying too hard. Women and men alike deserve options that fit well, wear well and stay sharp long after the date is over.
That’s why Lands’ End is your destination for dependable button-downs, flattering dresses, easy layers and real-life style for date night, for everyday and for life’s every journey.