This week I’m talking about what to wear on a date, out on the weekend, and to work. Where to start can be the hardest part so I break down the basics in here.

I talk through the style guides I built for each scenario and the essentials I recommend for each of them. I tell you what brands I like and where I recommend you shop especially with Black Friday and Cyber Monday coming up, it’s kinda the perfect time for this one.

The Ultimate Style Guide for Guys: What to Wear on Dates, Going Out, and to Work

Originally featured on the Guyset podcast - your guide to what should be talked about

Why Most Guys Need Style Help (And That's Totally Normal)

Here's the honest truth: most guys in their twenties don't have a developed sense of style yet. And that's completely okay.

This realization hit me hard recently when a friend screen-shared her Hinge profile to prove how rough dating apps can be. As she scrolled through profiles, one thing became crystal clear: the guys need some serious help with their style choices.

This isn't about being shallow - it's about presenting your best self and feeling confident in what you're wearing. Whether you're going on a date, heading out with friends, or trying to look professional at work, knowing what to wear shouldn't be a source of stress.

The Real Problem: Where Do Guys Go for Style Advice?

When I first moved to New York for a summer internship, my roommate and I faced the same question: "What the hell do we wear going out to a bar?"

We looked online and couldn't find practical, realistic advice for normal guys. Most style websites either:

• Show celebrity outfits we can't afford or pull off

• Give vague advice that doesn't help with specific situations

• Assume you already have a developed sense of style

That's exactly why style advice needs to be talked about more among guys. We're all figuring it out together, and there's no shame in needing guidance.

Building Your Style Foundation: The Basics

Before diving into specific scenarios, you need to build a solid foundation. Think of this as your style starter pack - basic pieces you can mix and match for almost any situation.

Essential Pants (Your Bottom Half Foundation)

Start with these five versatile options:

1. Black pants - dress up or down easily

2. Blue pants - navy works with almost everything

3. Khaki pants - perfect for casual-professional looks

4. Gray pants - neutral and versatile

5. Jeans - your weekend staple

Why these work: These colors can be paired with nearly any top, making outfit planning much simpler.

Essential Shirts (Your Top Half Basics)

Keep it simple with these core colors:

• White t-shirt - the ultimate versatile piece

• Black t-shirt - sleek and easy to style

• Gray t-shirt - pairs with everything

• Blue t-shirt - adds subtle color without being loud

Essential Layering Pieces

For dates and going out:

• Bomber jacket - casual but put-together

• Jean jacket - classic and versatile

• Khaki/barber jacket - slightly more refined

• Button-down shirt - white or striped

• Flannel shirt - perfect for layering

The key: These pieces allow you to look like you put in effort without overthinking it.

Scenario 1: What to Wear on a Date

The goal: Look like you care without looking like you tried too hard.

The Simple Date Formula

Base: Choose one of your essential pants + one of your essential shirts Layer: Add a jacket or button-down for polish Finish: Clean shoes and a belt that works

Real Examples:

• Casual dinner: Dark jeans + white t-shirt + bomber jacket + white sneakers

• Drinks date: Khaki pants + blue button-down + no jacket (if warm) + clean sneakers

• Nicer restaurant: Black pants + white button-down + jean jacket + dressier shoes

The Cologne Factor

Add a subtle cologne - not too much, just enough that she notices when she's close to you. Less is always more with fragrance.

Pro Tips for Date Dressing:

• Comfort is key - wear something you feel confident in

• Avoid brand new clothes - stick with pieces you know fit well

• Check the weather - nothing ruins a date like being uncomfortable

• Have a backup plan - keep a simple jacket or sweater handy

Scenario 2: Going Out with Friends

Good news: This overlaps significantly with date outfits. The same pieces that work for dates work perfectly for bars, casual hangouts, and weekend activities.

Weekend Going Out Formula:

• Base: Jeans or casual pants + favorite t-shirt

• Layer: Flannel, button-down, or casual jacket

• Shoes: Clean sneakers or casual shoes you can walk in

Bar-Specific Considerations:

• Dive bar: Keep it simple - jeans and a t-shirt work perfectly

• Nicer bar: Add a button-down or light jacket

• Rooftop/outdoor: Consider the weather and venue vibe

The beauty of having basics: You can grab any combination and look put-together without overthinking it.

Scenario 3: Work Attire

The challenge: Work dress codes vary wildly, from startup casual to corporate formal.

The Research Method

Before anything else, observe what others are wearing. This is your best guide because:

• Every workplace has its own culture

• You don't want to be overdressed or underdressed

• Following existing norms shows awareness and respect

General Work Guidelines:

Startup/Casual Office:

• Nice jeans or khakis

• Button-down or polo shirt

• Clean sneakers or casual shoes

Corporate/Professional:

• Dress pants (slacks)

• Button-down shirt

• Dress shoes

• Possibly a tie or jacket (observe first)

When in Doubt:

• Ask a coworker - "What's the typical dress code here?"

• Start slightly more formal - it's easier to dress down than up

• Have a suit ready - you never know when you'll need it

• Default option: Button-down + nice pants + dress shoes

Where to Shop: The Brand Guide

Perfect timing: With Black Friday and holiday sales, now's the ideal time to build your wardrobe without breaking the bank.

Budget-Friendly Options:

• Uniqlo - excellent basics at great prices

• J.Crew (on sale) - classic pieces that last

• Abercrombie & Fitch - surprisingly good quality basics

• Urban Outfitters - trendy pieces for going out

Mid-Range Reliable Brands:

• Levi's - for jeans and casual wear

• Bonobos - great pants and casual pieces

• Patagonia - quality outerwear and casual pieces

• Polo Ralph Lauren - classic preppy pieces

Investment Pieces:

• Rag & Bone - higher quality basics

• Theory - professional and refined pieces

• Vince - elevated casual wear

• Frame - premium denim and casual pieces

Don't Overlook:

• Lululemon - not just for workouts, great casual pieces

• Skims - excellent t-shirts and underwear

• Carhartt - durable jackets and workwear

• Todd Snyder - elevated basics

Shoes and Accessories: The Finishing Touches

Essential Footwear:

• White sneakers - work with almost every casual outfit

• Gray or beige sneakers - subtle alternatives to white

• Brown dress shoes - for work and nicer occasions

• Black dress shoes - formal events and professional settings

Belt Basics:

• Black belt - pairs with black shoes and formal wear

• Brown belt - matches brown shoes and casual outfits

• General rule: Try to match your belt to your shoes when possible

Popular Sneaker Options:

• Veja - trendy and versatile

• Vans - classic casual option

• Clean white Nike - athletic but stylish

• Common Projects - minimalist and premium (investment piece)

The Street Style Learning Method

Here's a game-changing approach: Start observing what well-dressed guys wear in real life.

How to Do This:

1. Notice outfits you like while walking around your city

2. Break down what works - what pieces, colors, combinations?

3. Find similar items at your budget level

4. Adapt to your lifestyle and comfort level

Why this works better than celebrity style: You're seeing real people in real situations, not styled photoshoots with unlimited budgets.

Common Style Mistakes to Avoid

The Overthinking Trap

• Don't stress about perfect combinations - basics are designed to work together

• Avoid buying everything at once - build your wardrobe gradually

• Don't copy someone else's style completely - adapt ideas to your personality

Fit Issues

• Too baggy or too tight - both look sloppy or uncomfortable

• Wrong length pants - should hit at the right spot on your shoes

• Ill-fitting shirts - shoulders should fit properly

Color Confusion

• Too many patterns - stick to one patterned piece per outfit

• Clashing colors - when in doubt, stick to neutrals

• Over-accessorizing - keep it simple, especially when starting out

Building Confidence Through Style

Start Small

You don't need a complete wardrobe overhaul. Pick 2-3 pieces from the essential lists and see how they work for you.

Focus on Fit

A $20 t-shirt that fits well looks better than a $100 shirt that doesn't. When in doubt, prioritize fit over brand names.

Develop Your Own Taste

Pay attention to what you feel good wearing. Confidence comes from feeling like yourself, not from copying someone else exactly.

The Comfort Test

If you're constantly adjusting or thinking about your outfit, something's wrong. Good style should make you feel more confident, not self-conscious.

Seasonal Adjustments

Fall/Winter Additions:

• Heavier jackets - wool coats, puffer jackets, or heavy cardigans

• Layering pieces - sweaters, hoodies, thermal tops

• Weather-appropriate shoes - boots or winterized sneakers

• Accessories - beanies, scarves (if that's your style)

Spring/Summer Modifications:

• Lighter fabrics - linen, cotton, breathable materials

• Shorter sleeves - t-shirts, polos, short-sleeve button-downs

• Lighter colors - whites, pastels, lighter blues and grays

• Breathable shoes - canvas sneakers, loafers, boat shoes

The Money-Saving Strategy

Sales to Watch:

• Black Friday/Cyber Monday - major discounts on everything

• End-of-season sales - great for building next year's wardrobe

• Anniversary sales - many brands have annual sales events

Investment vs. Budget:

• Invest in: Well-fitting jeans, quality shoes, versatile jackets

• Save on: Basic t-shirts, trendy pieces, items you're unsure about

Building Over Time:

Don't feel pressure to buy everything at once. Start with one scenario (like dating) and gradually expand your wardrobe for other situations.

Taking Action: Your Style Game Plan

Week 1: Assessment

• Look through your current wardrobe - what do you already have?

• Identify gaps - what scenarios do you struggle to dress for?

• Make a list of 3-5 essential pieces you need most

Week 2: Research

• Check out the recommended brands during sales

• Observe styles you like in your daily life

• Ask friends for honest feedback on your current style

Week 3: Strategic Shopping

• Start with basics - pants and shirts in neutral colors

• Focus on fit - try things on or check return policies for online orders

• Stick to your list - don't get distracted by impulse purchases

Week 4: Practice

• Try different combinations with your new pieces

• Get comfortable wearing your new style

• Ask for feedback from trusted friends or family

The Confidence Connection

Remember: Style isn't about impressing others or following rules perfectly. It's about feeling confident and comfortable in your own skin.

Good style helps you:

• Feel more confident in social situations

• Make better first impressions

• Express your personality appropriately

• Stop worrying about what you're wearing

The goal isn't perfection - it's having reliable options that make you feel good about how you present yourself to the world.

Beyond the Basics: Growing Your Style

Once you've mastered the fundamentals, you can start:

• Experimenting with colors beyond neutrals

• Adding personality pieces that reflect your interests

• Trying different fits and silhouettes

• Investing in higher-quality pieces that last longer

But for now, focus on the basics. Master the foundation before adding complexity.

The Bottom Line

Style doesn't have to be complicated or expensive. With a few essential pieces in versatile colors, you can handle most situations life throws at you.

The key principles:

• Start with basics that work together

• Prioritize fit over everything else

• Observe and learn from styles you admire

• Build gradually rather than buying everything at once

• Focus on feeling confident rather than following trends perfectly

Most importantly: Every guy is figuring this out as he goes. There's no shame in needing guidance, and small improvements in how you dress can make a big difference in how you feel about yourself.

Your style journey starts with one good-fitting pair of pants and a shirt you feel confident wearing. Everything else builds from there.

Want more style advice and tips for navigating your twenties? Listen to new episodes of Guyset every Tuesday on your favorite podcast platform. Follow @guysetstyle on Instagram for visual style guides and outfit inspiration. Sign up for the weekly newsletter at guyset.com, email josh@guyset.com with your questions, or connect with us @theguyset on social media.

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See you guys next Tuesday.