What to Wear on a First Date (Even If It Has Been a While)
Written by Artemis Clo
Whether it is your first first date in twenty years or simply the first with this particular person, knowing what to wear on a first date takes one thing off your mind. The aim is not to impress. It is to feel so comfortable that you forget about your clothes and pay attention to the company.
What to wear on a first date: start with yourself
The best first date outfit is one you have already worn and loved. Think of the last time someone complimented you, or the last time you caught sight of yourself in a shop window and thought, oh, that is nice. Start there. Whatever it was, it suited you and you felt at ease in it, and that ease is exactly what you want to bring along.
A good top does a lot of the work, because it is what your date will see across the table. A satin cowl neck blouse with a shirt collar is easy to dress up or down, while a fine-knit V-neck top with painterly stripes feels relaxed and still put-together. Our tops and shirts collection has plenty more in soft, easy shapes.
Avoid anything you have to keep adjusting: a neckline that slips, a skirt that rides up, a waistband you notice when you sit. You will be sitting for most of the date, so try your outfit in a chair at home before you leave.
Tops & Shirts to start with
A few pieces that fit what you have just read.
Satin Cowl Neck Blouse with Shirt Collar
Fine-Knit V-Neck Top with Painterly Stripes
Notch Neck Blouse with Petal Sleeves
Match the outfit to the plan
Where you are going matters more than any rule. A few easy first date outfit ideas, by plan:
- Coffee or a daytime walk. The casual first date outfit: jeans or relaxed trousers, a soft top or jumper and a jacket you like.
- Drinks in a bar. Your favourite trousers with a top that has a little sheen or a good neckline, and boots with a modest heel.
- A dinner date. A midi dress or smart separates, a layer for the walk home and a small bag.
- Something active. If it is a gallery, a market or a country walk, flat shoes and layers win every time.
For dinner, a wrap midi dress feels like an occasion without trying too hard, and the dresses range covers everything from relaxed to polished. If the place is somewhere in between, our guide to the smart casual dress code is a handy rule of thumb: polished enough for a nice restaurant, relaxed enough for a pub. If you would rather wear trousers, a pair of high waisted palazzo trousers with a bow tie belt looks smart and moves beautifully. More shapes are in the trousers collection.
If the plan is a show or a concert first, our notes on what to wear to the theatre apply nicely to a date too.
Shoes you can walk in
A first date has a habit of turning into a stroll. You might walk to a second bar, or along the river, or simply to the station while you finish a conversation neither of you wants to end. The right first date shoes let you say yes to that.
A pair of ankle boots with a low or medium heel is the easy answer for most of the year. Zip wedge ankle boots with a layered sole give you a little height with plenty of steadiness, and they work with jeans, trousers and dresses alike. Our boots collection has flat and heeled styles for every kind of plan.
If you really want to wear the heels, carry flats in a bigger bag. There is no shame in it, and plenty of romance in a woman who can keep walking.
Deciding what to wear on a first date the night before
Choose your outfit the evening before and lay it out, bag and all. It takes the rush out of getting ready and leaves your nerves with less to work on. Check the weather, and add a layer you are happy to be seen in, because a borrowed jacket is charming in films and less so in real life.
Keep jewellery and scent light. One piece you love is plenty, whether it is earrings, a necklace or a ring with a story. Your date should remember you, not the clattering bracelets.
A small bag is better than a big one. You want room for your phone, keys, a card and a lipstick, and nothing that needs its own chair. A bag with a strap leaves your hands free for a glass, a menu or, if things go well, a hand to hold on the way home.
Then stop thinking about it. If you feel like yourself on a good day, you have chosen well. If it all goes beautifully, you will have the pleasure of deciding what to wear on the second date. If it does not, you will at least have had a lovely evening out in a favourite outfit.
Next, from our boots
Something from a neighbouring rail, for the same moment.
Suede-Look Western Ankle Boots with Pull Tabs
Zip Wedge Ankle Boots with Layered Sole
Orthopaedic Laser-Cut Ankle Boots with Block Heel
Your questions, answered
Should I dress up or down for a first date?
Aim for one notch above what you would wear to meet a friend at the same place. That way you look as though you made an effort without looking as though you are going somewhere else afterwards.
Is a dress too much for a first date?
Not at all, as long as it suits the setting. A knit or printed day dress with boots feels relaxed enough for coffee, while a midi with a little more polish works for dinner.
What colours work well on a first date?
The ones you feel good in. Colours near your face that you are regularly complimented on are a safe bet, and a soft jewel tone or a warm red often looks lovely in candlelight.
Should I wear something new?
Only if you have worn it at least once before. New clothes have a way of revealing a scratchy label or a gaping button at the worst moment, so give anything new a trial run first.
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