;Crop=(0,0,4096,2732),gravity=Center)
WHAT TO WEAR ON A DATE:
EASY OUTFIT IDEAS FOR MEN
Deciding what to wear for a date should get you geared up and ready to go - not leave you stressed on your way out the door.
Whether you’re meeting someone for the first time or going for a long-overdue evening out with your partner, the goal is to look like a polished version of yourself. A great outfit acts as a silent confidence booster, helping you relax and get the conversation flowing.
…And that’s where we come in! In this guide, we’ll break down date night outfit ideas for men that’ll keep you comfortable and looking the part, no matter where you’re going or who you’re going with.
HOW TO CHOOSE THE RIGHT DATE NIGHT OUTFIT
The key to a winning date night look is getting the right vibe. You want to match the energy of the venue while staying true to your personal style.
Think about the type of date
Before you start planning your outfit, think about the activity. A coffee will call for a far different outfit than a three-course dinner, for example. And dressing too formally for a casual walk can feel stiff, while showing up to a cocktail bar in a tracksuit might seem like a lack of effort.
Check out the venue before you go, get an idea of the expected dress code, and go from there.
Dress for confidence, not just style
If you feel self-conscious or restricted in what you’re wearing, it’ll show in your body language. That’s why comfort should come first. If you prefer jeans over trousers, find a high-quality pair of slim pants for men that fit perfectly, rather than forcing yourself into a suit that feels unnatural.
Keep effort visible but natural
You want your date to see that you’ve put in effort, but you don’t want it to look forced. This is often achieved through small details: an ironed shirt, clean shoes, a neat hairstyle. It’s about looking intentional without appearing like you’ve spent three hours in front of the mirror.
WHAT TO WEAR ON A CASUAL DATE NIGHT
For everything from daytime dates to low-key evening plans, the focus should be on smart-casual essentials.
RELAXED LAYERS
A perfect-fit t-shirt in a neutral colour is a solid starting point. To make it feel more like a date night look, add a lightweight knit or an unbuttoned overshirt - this adds depth and a practical layer in case the temperature drops.
JEANS & TROUSERS
Dark denim is the versatile choice men can always rely on for casual date night outfit ideas. Avoid heavily distressed styles or baggy cuts, and choose a clean indigo or black wash instead. If jeans feel too casual, a pair of comfy chinos can make a smart alternative.
LAID BACK FOOTWEAR
Clean, minimalist trainers are great for casual dates - just make sure they’re scuff-free and paired with invisible or tonal socks. If you want something between a trainer and a formal shoe, a desert boot or a casual loafer will always look the part.
WHAT TO WEAR FOR A DINNER-AND-DRINKS DATE
If you’re planning an evening out at a bar or restaurant, it’s time to sharpen the silhouette.
SHIRTS & SMART LAYERS
You can’t go wrong with a men’s shirt for special occasions here. A classic button-down Oxford or a shirt with a subtle pattern works well. If the atmosphere is more relaxed, you can layer it with a crew-neck jumper, letting the collar peek through for a structured look.
TAILORED TROUSERS
Dinner and drinks is the perfect time to pull out your black dress trousers or tailored chinos. If you choose denim, keep it dark and pair it with a more formal top to balance the outfit. This keeps you looking sophisticated for a nice meal, but relaxed enough for drinks afterwards.
SMART FOOTWEAR
Evening dates mean smart shoes. Chelsea boots hit the perfect balance between smart and casual, while leather Derby shoes or polished loafers will instantly refine the entire outfit.
WHAT TO WEAR FOR A FORMAL DATE NIGHT
From anniversary dinners to fancy theatre trips, some occasions will need a more refined approach.
BLAZERS & JACKETS
Adding a blazer is the easiest way to upgrade your outfit. Perfect for special dates, a navy or grey one will pair with contrasting trousers for a timeless, masculine look. The jacket will help to frame your torso, and it adds a layer of authority to your appearance too.
FORMAL FOOTWEAR
For formal settings, we recommend sticking to slick leather footwear. A polished black or dark brown pair of shoes will complete the look perfectly - just make sure your belt matches to keep the outfit cohesive.
SMART SHIRTS
A white shirt is the staple for any man’s evening outfit, especially ones made from high-quality cotton to hold their shape. If the date is part of a larger celebration, pair it with pieces from our mens evening wear range to make sure you’re the best-dressed man in the room.
DATE NIGHT OUTFIT MISTAKES TO AVOID
1. Trying too hard: Wearing a full suit to a casual pub will grab attention for all the wrong reasons. Try to match the energy of the venue instead.
2. Wearing something uncomfortable: Don’t wear a shirt that’s too tight or trousers that dig in. You want to feel your best, so pick something comfy.
3. Ignoring the setting: Always check if the venue has a dress code. Showing up in trainers to a no-kicks zone is a quick way to put an end to your date.
4. Overdoing accessories or fragrance: A watch and ring are usually enough, and one or two sprays of aftershave is plenty; you want the scent to be discovered, not announced.
5. Wearing something completely new: Avoid wearing brand-new shoes that might give you blisters, or a shirt you haven’t tested for sweat patches. Stick to items you know look and feel good.
DATE NIGHT OUTFITS DONE RIGHT
The best men’s date night outfit ideas are the ones that let your personality shine through.
Whether you’re going for a coffee or fancy dinner, your date wants to know that you’ve taken time to look your best. By combining comfortable fits with smart staples from Jacamo, you can step out the door knowing you’re about to put your best foot forward.