Effortlessly Stylish Date Outfit Ideas

20 July 2022 | 8 mins

The Psychology of Looking Good Looking good is a strategy, not vanity. The concept of dressing well can be broken down into two core factors, the first is down to personal preference and taste. How we choose to dress showcases how we see and feel about ourselves. The second factor, is of course, how others […]

The Psychology of Looking Good

Looking good is a strategy, not vanity. The concept of dressing well can be broken down into two core factors, the first is down to personal preference and taste. How we choose to dress showcases how we see and feel about ourselves. The second factor, is of course, how others view us and how we want to be perceived by the outside world.

Everything we do visually is an active recognition of how we communicate with ourselves and others. Whether it’s a new haircut, what jewellery we wear or how long we spend at the gym to achieve the ideal figure, these decisions have a positive knock-on effect on our state of mind. We feel good when we make conscious decisions to enhance our appearance. “Clothing is rich with meaning and purpose. The link between clothing and emotions is reciprocal—how we feel impacts what we think about our clothing, and it guides our decisions about what to wear. But what we wear also impacts how we feel and what we think” says Daniel Benkendorf, an associate professor of psychology at the Fashion Institute of Technology.

Why does this matter when considering date outfit ideas? Because once you find a date outfit you like, it automatically boosts your confidence and self-esteem, two crucial components for striking a great first impression on a date. Self-affirmation plays a huge role in how we approach that first date and when we’re happy with how we look, it helps to alleviate those classic first date outfit anxieties.

‘Enclothed cognition’, a term coined by cognitive psychologists Hajo Adam and Adam Galinsky, looks at the relationship between the clothes we wear and the influence they have on the wearer’s psychological processes. In short, how we dress affects how we feel.

The ‘7-second Impression’

High-achievers walking together as a couple

Strictly speaking, there is no ‘rule’ for what to wear on a first date. Your date outfit should make you feel comfortable and confident, don’t feel as though you have to rock a stunning dress and high heels or a suave suit if it’s not your style or doesn’t align with the location or setting of your date. Of course, there are some things you can do to maximise the first ‘7-second’ impression before your date, but when it comes to date outfit ideas, remember, this is a date, not a job interview! Be comfortable, be cool and let your personality do the work.

Practical Steps to Dressing Well Before your First Date

It’s not uncommon to open your wardrobe when approaching the first date and think “I’m not sure I like any of this!” and there are a few reasons for this. As we mentioned before, it’s not about what your clothes look like, it’s more about how your clothes make you feel.

One reason might be that you have gone through a major change in your life and want your clothes to symbolise this. Alternatively, maybe your wardrobe harbours memories of a negative time in your life. Whether it’s a dress that reminds you of that time you went to a special event with an ex or items of clothing you associate with an ex-partner – understandably, you want to purge this clothing and start afresh.

Whatever the reason, it’s important to be proud of your wardrobe in your approach to a first date. If you’re unhappy with what you’re looking at, don’t be afraid to recycle some items. In most cases, much of your wardrobe will be salvageable. For example, black shift dresses and fitted suits never go out of style, so pair that black dress with a cardigan, a nice jacket and a statement necklace to refresh and revitalise your dress. For guys, most suit trousers are versatile, so pair this with a white or black shirt, a brown or black belt and smart trainers.

It’s important to at least attempt to work with your existing wardrobe, rather than against it. Don’t be afraid to experiment with your wardrobe before you start culling, you might be surprised at what new combinations you invent!

What to Wear on a First Date

How to prepare for a date

Whether it’s spring, summer, autumn or winter, your date outfit ideas need to match the season and the location where your date is taking place. First dates already invite natural nervousness, so we don’t want to add complex fashion to the equation. Keep things simple and wear what makes you feel confident and comfortable. Below are a few timeless classics we think would work well as first date outfits. Or alternatively, learn what to wear on a first date from personal stylist & image consultant, Deni Kiro.

Without further ado, let’s take a look at some timeless and simple date outfit ideas.

Spring Date Outfit Ideas

The start of a new season means the start of a new outfit. For spring, don’t be afraid to symbolise the season with floral prints and lighter colours. You can always pair your outfit with a jacket or blazer if it becomes chilly in the evening. We’ll be sticking mostly to casual date outfit ideas below, as it’s likely your first date will be in a less formal setting.

For men: A relaxed look for spring is always a winner. Keep it comfy and casual with dark jeans, a light striped sweater with a tan oversized shirt or a jacket that keeps things crisp but casual. If you’re looking for a slightly dressier look for this style, tuck in your shirt and wear a belt. Partner this with smart white trainers or combat boots for a more rugged look.

For women: Floral prints are always a fun and versatile choice. The classic spring dress is a safe bet, however, if you’re looking to switch things up, go for a floral crop top and skirt or blue denim jeans. Pair this with white trainers or boots (Doc Martens are timeless) and a black leather jacket if this is an evening date.

Summer Date Outfit Ideas

For men: Stick to pale or pastel shirts, a white Oxford shirt never goes amiss at this time of the year and pairs up nicely with almost any trousers. If it’s a particularly hot day, swap this out with silk or patterned viscose shirts. We’d personally go with light blue jeans or tan chinos, paired with dark brown smart shoes or boots. Partner this with a tanned or black jacket for the evening.

For women: A pastel pink gingham shirt paired with white jeans is an effortlessly iconic summer date outfit. It’s light, airy and ideal for people who value comfort just as much as style. For shoes, feel free to be flexible, white trainers will work just as well as peach heels, just be sure to choose appropriate footwear if your date revolves around taking a trip through a botanical garden or anything that involves a bit of walking!

Autumn Date Outfit Ideas

For men: Autumn presents some fantastic date outfit ideas for men and every guy looks great in autumnal tones. Start with a charcoal cashmere sweater and pair this with some black or dark blue jeans. Alternatively, don a cashmere cardigan partnered with a white fitted t-shirt for a more casual look. Both options provide warmth without bulk or weight and cashmere can be worn on the skin, unlike coarser wools and materials. Stick to earth tones for shoes, preferably dark boots to finish the rugged autumnal aesthetic.

For women: one of the best ways to make your summer outfit look more autumnal is to switch out the lighter tops for darker ones. A black shirt tucked into denim jeans paired with lace-up boots is always a winning combination. If this feels too similar to the above, why not opt for something a little off-piste? Don’t be afraid to work blazers into your wardrobe. A dogtooth or light grey blazer matched with a white shirt or t-shirt and dark denim jeans borders perfectly on the smart-casual line. Ideal for evening bar dates as well as lunches.

Winter Date Outfit Ideas

For men: denim is the go-to for men’s winter fashion. It’s versatile, warm and perfect for both casual and evening date ideas. Stand out with a burgundy coat with white fur for a casual and warm look. Pair this with slim black jeans, a black t-shirt or shirt (for evening dates) and plum-coloured boots to complete this dark and inviting aesthetic. The burgundy jacket and plum boots will become a subtle focal point against the minimalist blacks.

For women: we’re bringing the moto jacket back for this one. Pair this versatile jacket with a tanned slit sweater skirt and matching boots for an effortlessly elegant look. If you’re heading out to your date after work, this winter outfit is perfect as you won’t need to bring a change of clothes to work.


It’s More Than Just an Outfit

Couple Walking Along South Bank On Winter Visit To London

What we wear is a visual representation of not only our personalities but how we want to be perceived. Whether you’re someone who enjoys spending time perusing and purchasing outfits for every season or someone more laid back who keeps things minimal throughout the year, there’s no right or wrong date outfit. Wear what makes you feel good, comfortable and confident to help you make a great first impression.

Of course, dressing well isn’t everything. If you struggle with date confidence or haven’t been on a date in a while, this is something we can help with. As professional UK matchmakers, we specialise in providing personal and bespoke introductions to exceptional people across the world. Everything about our service is tailored to you, whether it’s private and personalised matchmaking or you’d like to speak to a qualified date coach to help you feel your best for your first date, we’re here to help.

Even if it’s just for a call, get in touch with us today to see how we can transform your view on dating and help you find your perfect partner.

Rachel

About the Author

Rachel Vida Maclynn

Founder & CEO

Rachel Vida MacLynn is reputed as being a world-leading matchmaking and dating expert. Registered as a Chartered Psychologist with the British Psychological Society, Rachel advocates a professional matchmaking approach based on psychological principles and professional consultation.

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