It’s your first date and you want to everything to be perfect. You’ve picked out the right place to go and have decided which flowers to pick up on the way over. You’ve had your hair cut last week and now it’s time to decide what to wear.
The key to dressing fashionably is to take you and tweak it a bit to maximize your style. No matter where you’re headed, the key to looking great is to dress for the occasion while preserving who you are at the core. Here’s how to put together the right pieces for right kind of look you want to go for.
Not quite old-school, not quite metropolitan and best of all, designed with a minimalist concept. The hipster in the city is a fusion of new and old for a look that's smooth and intellectual yet casual and easy-going.

Trend Alert:
Straight leg pants are today’s most popular fit. If you need more room, try pants that are slightly slouchy but not baggy. This same notion applies to tops. Avoid wearing shirts that are too tight or too revealing. Opt for just fitted. Keep it classic and stick with conservative colors like solid blacks, whites, grays, browns or beiges.
For a more casual style, leave your collared shirt untucked and cuff sleeves to a 3/4 length. For an added flair, layer a cotton sports jacket on top. Quick Tip: Keep the length of your shirt even with the hips if wearing un-tucked.
Go Trendy: Generally, it’s a good rule of thumb to veer towards simplicity on the first date. You want to blend classic pieces so that you look nicely put together but not go over-the-top so that your outfit distracts from you.
Escape a fashion no-no by picking just one piece of your outfit to accentuate. It can be anything from your shoes, sweater, or jacket. Keeping minimal in mind, here are some examples of how you can combine your basics with some of today's new styles.
| Outerwear | Top | Bottom | Shoes |
| Brown Houndsooth Blazer | Tan solid button-up | Denim fitted jeans | Brown lace-ups or loafers |
| Argyled or striped sweater , say in black/gray | Gray polo (match undershirt with one of the colors in the sweater) | Flat front trousers | Black lace-ups or loafers |
| Oxford with military inspired detailing i.e. chest flap pockets or epaulettes | Denim fitted jeans | Brown lace-ups or loafers | |
| Navy cotton blazer | Light blue tee or v-neck sweater | Denim fitted jeans | White canvas sneakers |
Where This Works:
- Happy hour
- casual dinner
- casual party
- a night out in town
You have to suit up for the occasion but it doesn't mean you have to dust off the three-piece. How do you command a look that’s refined but not stuffy, classic yet modern, and structured but comfortable?

Here are some ways to dress up the black suit:
–Boldly striped ties –Satin ties (try metallic silver, pink or purple) –Black calfskin leather belt with silver hardware –Silver cufflinks or studs –Satin pocket handkerchief for an old Hollywood flair –Black patent leather lace-ups designed with a narrow toe boxQuick Tip: Shoes can carry as much weight as an expensive wristwatch, so at the very least, they should be clean and polished.
Go Trendy: Mix up your suit outfit. Instead of "that jacket" that goes with "those pants," you can swap your jacket with one of three options:
- A blazer of a different texture i.e. a luxurious velvet
- A waistcoat
- A thin sweater over your button-down
To celebrate summer, opt for a lightweight cotton suit in light beige or ivory.
If you’re looking to substitute your traditional white dress shirt, try a solid pink, midnight blue or royal purple. Try to avoid neon colors or metallic sheens which can deter from the rest of your outfit. When in doubt, your safe bet is to contrast dark and light hues.
Quick Tip: When looking for the right dress shirt, it’s important to get measured for fit. You want the shirt to fit properly at the neck and sleeves and tailored correctly so that it eliminates the billow and fits snugly against your body.
For your bottom, pinstripes lining the vertical of your pants can do masterful job of creating a look that’s ultra sophisticated.
Where this works:- Romantic dinner
- Theater
The style is laid-back. You can leave your more experienced clothes in the drawer, say your favorite jeans or T-shirt and still feel as comfortable as you look. Here’s how you can gear up fashionably for a casual day out.

Go Classic: When you're in the stands, play with a brightly colored polo or a pocketed basic T-shirt. Quick Tip: If possible, opt for a plain top, one that's void of any flashy lettering or logo.
Layer a long-sleeve tee underneath if the weather is mild. Hide your head beneath a zippered hooded top for that hot day turned cool night. Indulge in soft and lightweight materials like cashmere and merino. Quick Tip: The zippered top is functional yet fashionable because you can layer but take on or take off with ease.
Match with chino or linen shorts. Or try a faded denim jean in both color and density.
Go Trendy:
When you’re on the green, you can match your pique polo shirt with a pair of plaid or seersucker shorts. Trend alert:
White is clean and crisp for summer. You have your simple white shirt varieties in crew, collar, or v-neck or white shorts in chino or linen.
A weathered button down in stripes or plaid can add another dimension to your outfit. Try bold yellow and blues or greens and oranges.
Make it snappy and wear a sweater vest over your T-shirt or polo.
On your feet:
- Leather thong or slide sandals
- White canvas sneakers
Where this works:
- Museum
- Walk in the park
- Coffee
For clothes befitting a day outdoors, the look is in the make. You want to be able to bend, stretch, jump and play in a get-up that not only looks hot but can also take the heat.

Go Classic: For an athletic first date, opt for a style that’s constructed but not constrained. It’s important to wear breathable materials like cotton or nylon. Match a plain basic T-shirt or polo with cargo shorts. If cargo is too heavy, opt for a pair of nylon shorts. A cotton-hooded sweatshirt or track jacket is perfect for when the sun goes down. If hitting the waves, consider board shorts decorated in camouflage or a fun Hawaiian motif.
Go Trendy:
With this look, you can be more liberal in your color choice. Work from a palette of solid colors for a look that’s clean and crisp. For a daring but summery celebration, try a bold yellow or orange.
Quick Tip: Remember learning complementary colors in art class? Use a color wheel as a general rule of thumb. Combinations using colors directly opposite each other or next to each other work well together.
On Your Feet:
- Sneakers appropriate for the activity
- Rubber slide sandals or thong sandals
Where this works:
- Hiking
- Sporting event
- Beach














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