What to Wear on a First Date: Style Tips, Outfit Ideas & Your Perfect Fit with Tellar

A first date is a moment to shine. Your outfit should help you feel confident, reflect your style, and suit the occasion—whether it's a casual coffee, an evening dinner, or something more active. Here's a comprehensive, no-fluff guide to dressing your best, then how Tellar makes sure it fits perfectly.

1. Dress for the Occasion

Casual Meet‑Ups (coffee, daytime strolls):

Aim for a smart-casual look with relaxed but polished pieces—think straight-leg jeans, a neat blouse, or a crisp casual shirt and chinos.

Evening/Dinner Dates:

Elevate your style. Midi dresses or sleek trousers with a blazer work well. For men, dark denim or tailored trousers with an Oxford shirt and optional blazer is a go-to.

Outdoor/Active Dates:

Focus on comfort without compromising hygiene. Choose activewear that looks put-together—leggings or stretch joggers paired with fitted tees or lightweight shirts.

2. Universal Styling Advice

Keep it true to your style: Your outfit should reflect you. Avoid looks that feel forced.
Fit is everything: Well-fitting clothes look effortlessly polished. A small adjustment can transform your look.
Comfort equals confidence: Pick fabrics and cuts you're at ease in—avoid anything you’ll fidget with.
Pick a focal point: If you're rocking bold shoes or a vibrant top, keep the rest subdued to balance the outfit.

3. Specific Outfit Inspirations

Occasion	Women	Men
Casual Coffee Date	Straight-leg jeans + tucked-in blouse + loafers	Slim chinos + casual shirt or crew jumper + desert boots
Evening/Dinner	Midi wrap dress + stylish booties or mules	Dark denim/trousers + Oxford shirt/knit polo + blazer
Active/Outdoor	High-rise leggings + cropped top + lightweight overshirt	Stretch joggers + fitted tee + utility jacket

4. Grooming & Details Matter

Add finishing touches: polished shoes, pressed clothes, and subtle fragrance. For ladies, light makeup and minimal accessories add polish. For men, neat grooming—whether it’s a tidy beard or a fresh shave—makes a strong statement.

5. What to Avoid

Steer clear of:

Shoes you can't walk in
Loud logos or overly distracting patterns
Overly revealing or excessively tight clothes
Anything new or untested—your first date isn't the time for a style experiment

6. Make Sure It Fits – Try Tellar’s Fit Tool

No more size-guessing! Tellar’s free sizing tool shows you what size works best across hundreds of brands based on your measurements or known sizes.

How Tellar works:

Enter your body measurements (or select your known size in a brand).
Choose from over 1,500 brand-specific size charts.
Instantly get your perfect size recommendation in seconds.

It works across gendered lines, UK/EU/US systems, and hundreds of iconic brands.

7. Styling & Fit Resources on Tellar

Explore these live styling deep dives and sizing guides:

Find out if Reiss runs small: Tellar’s Reiss sizing guide
See how COS sizes compare internationally: Why COS sizes feel inconsistent—and how to get your fit right
Perfecting Zara fits for men: Zara men sizing guide
Tips for elegant evening wear: Smart casual dress code decoded: men & women
Best petite-friendly brands: The best brands for petite women

8. Ready for Your Perfect Date Outfit?

Confidence + fit + the right vibe = your best first-date look. No guesswork needed—Tellar helps ensure your outfit not only looks great but fits flawlessly.

🌟 Get started now at Tellar.co.uk 🌟

Stay Connected with Tellar

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Twitter/X: @Tellar100
Facebook: Tellar Sizing
Pinterest: TellarUK

Dress like yourself, only sharper—and let Tellar take care of the rest.