Key Takeaways:
- Choose outfits based on date location and activity
- For casual dates, pair well-fitted jeans with a crisp t-shirt and stylish trainers
- Formal dates call for a soft-shoulder blazer and dark trousers with loafers
- Balance dressy and casual with drawstring trousers and a knit top for drinks dates
- Layer with overshirts or cashmere pieces for versatility
- Pay attention to fit, cleanliness, and overall presentation
- Dressy sneakers can elevate a casual outfit for a trendy date spot
- Consider custom-tailored suits or sport coats for a perfect fit and lasting impression
- Confidence is key - wear outfits that make you feel comfortable and stylish
- Don't forget the details, like fresh breath and well-maintained shoes
How to Dress for a Date: Expert Tips for Men and Guys
Are you wondering what to wear on a first date? Whether you're in your 40s or just starting out in the dating scene, choosing the right outfit can be a challenge for guys. The best thing to wear on a date often depends on the setting and activity, but there are some general guidelines that can help you make a great first impression.
Have you ever found yourself staring at your wardrobe, unsure if it's OK to dress casual for a date or if you should opt for something more formal? You're not alone. Many men struggle with this decision, especially when trying to figure out what to wear on a first date for drinks or a casual meetup.
What if you could learn how to dress for a date with confidence, knowing you'll look your best no matter the occasion? In this guide, we'll explore expert tips on how to dress for a date, covering everything from casual outings to more formal affairs. We'll answer common questions like "What is the best color to wear on a first date?" and provide practical advice for men of all ages.
Ready to transform your dating wardrobe and boost your confidence? Let's dive into the world of date-night fashion and discover how to make the right impression with your style choices.
What to Wear on a Casual First Date: Coffee, Quick Bite, or Park Walk
For casual first dates like grabbing a coffee, having a quick bite, or taking a stroll in the park, the key is to strike a balance between being impressive and comfortable. You want to show that you've made an effort without appearing overdressed for the occasion.
Start with your favourite pair of well-fitted jeans. A dark wash denim is versatile and can easily be dressed up or down. Pair this with a crisp, clean t-shirt in a solid colour or subtle pattern. The t-shirt should be in good condition, free of wrinkles or stains, to show that you care about your appearance.
For footwear, opt for a pair of stylish, comfortable trainers. Choose a clean, well-maintained pair that complements your outfit. Remember, your shoes say a lot about you, so make sure they're in good shape.
To add a touch of sophistication and prepare for any weather changes, top off your look with a soft wool overshirt. This layering piece not only adds warmth but also elevates your casual outfit, showing that you've put thought into your appearance.
When selecting colours, consider neutral tones like navy, grey, or earth tones for a timeless look. If you want to add a pop of colour, do so with your t-shirt or overshirt, keeping the rest of the outfit relatively muted.
Dressing for a Formal Date: Elevating Your Style
When your date calls for a more refined look, it's time to step up your style game. A formal date might include dinner at an upscale restaurant, attending a cultural event, or any occasion where you want to make a strong impression with a sophisticated outfit.
For this type of date, consider a double-breasted, grey, soft-shoulder blazer. The double-breasted style adds a touch of classic elegance, while the soft shoulder keeps the look modern and comfortable. Grey is an excellent colour choice as it's versatile and flattering on most skin tones.
Pair your blazer with dark grey trousers. The monochromatic look creates a sleek, elongating effect that's both stylish and flattering. Ensure your trousers are well-tailored, with a clean break at the shoe.
Instead of a traditional shirt and tie combination, opt for a cashmere and silk knit top. This choice adds texture and luxury to your outfit while maintaining a relaxed sophistication. It's an unexpected twist that shows you're fashion-forward and not bound by conventional rules.
For footwear, a nice clean loafer is an excellent choice. Loafers strike the perfect balance between formal and relaxed, and they're comfortable for a night out. Choose a pair in a dark colour like black or deep brown to complement your grey ensemble.
When accessorising, keep it minimal. A simple watch and perhaps a pocket square in your blazer can add just the right amount of detail without overwhelming your look.
What to Wear on a First Date for Drinks: Balancing Dressy and Casual
When you're heading out to the hottest new spot in town for dinner and drinks on a first date, you need an outfit that strikes the perfect balance between dressy and casual. This look should convey that you're stylish and put-together, but also relaxed and ready for a fun evening.
Start with a pair of drawstring cotton trousers. These offer a modern twist on traditional formal wear, providing both comfort and style. Choose a neutral colour like navy, khaki, or charcoal that will pair well with various tops. The drawstring waist adds a casual element, while the overall cut keeps the look refined.
For your top, opt for a winter white knit. This choice adds a touch of sophistication and brightens your overall appearance. The texture of the knit provides visual interest and depth to your outfit. Layer this with a cashmere overshirt in a complementary colour. This layering not only adds warmth but also gives you the option to adjust your look as the evening progresses.
When it comes to footwear, elevate your outfit with a pair of dressy sneakers. Look for sleek, minimalist designs in high-quality materials like leather. White or light-coloured sneakers can work well, creating a nice contrast with darker trousers. This footwear choice perfectly embodies the balance between casual and dressy that we're aiming for.
Accessorise minimally with a watch that complements your outfit. If you wear jewellery, keep it subtle - perhaps a simple bracelet or a pair of cufflinks if your overshirt allows for it.
Remember, the key to this look is the mix of textures and the play between casual and formal elements. The drawstring trousers and sneakers keep things relaxed, while the knit top and cashmere overshirt add refinement. This combination shows that you're fashion-forward and adaptable - great qualities to communicate on a first date.
Lastly, don't forget the small details. Ensure your clothes are well-pressed and free of any stains or wrinkles. And as our expert Winston reminds us - don't forget the mints! Fresh breath is the perfect finishing touch to any date night outfit.
Elevate Your Date Night Style with Westwood Hart
Now that you're equipped with expert advice on how to dress for various date scenarios, why not take your style to the next level with a custom-tailored suit or sport coat from Westwood Hart? Our bespoke garments are perfect for making a lasting impression on any date, from casual coffee meetups to formal dinner engagements.
Imagine stepping out in a perfectly fitted blazer that accentuates your best features, or a custom suit that feels like it was made just for you – because it was. Westwood Hart's online configurator allows you to design your ideal suit or sport coat from the comfort of your home. Choose from a wide range of high-quality fabrics, customise your lapels, pockets, and buttons, and create a garment that truly reflects your personal style.
Whether you're looking for a versatile sport coat to dress up your jeans and t-shirt combo, or a full suit for those special date nights, Westwood Hart has you covered. Our expert tailors ensure that every piece fits you flawlessly, giving you the confidence to focus on what really matters – enjoying your date.
Ready to transform your date night wardrobe? Visit Westwood Hart's website today and start designing your perfect custom suit or sport coat. With Westwood Hart, you'll always be dressed to impress, no matter where your dating adventures take you.