dress to impress: A man’s Speed dating style guide
You've got your ticket. You've practiced a few conversation starters. Maybe you're even feeling a little confident.
Then comes the question every guy asks before a speed dating event:
"What am I supposed to wear?"
The good news? You do not need a designer wardrobe, an expensive watch, or a perfectly curated Instagram aesthetic to make a great first impression. The goal is not to look like someone you're not. It is to show up looking like the best version of yourself.
At our speed dating events, we see it all. Guys who show up in gym shorts. Guys who wear full suits. Guys who spend the entire night wishing they had put a little more thought into their outfit. The sweet spot is usually somewhere in between.
That is why we created this guide. Inside, you'll find the essential wardrobe pieces every man should own, along with examples of how to style them. Think of it as a practical roadmap for looking confident without overthinking it.
TOPS
The Boxy T-Shirt
A heavyweight boxy tee with a structured fit is one of the easiest ways to elevate a simple outfit. The slightly oversized silhouette feels modern and intentional while still being comfortable.
When in doubt, reach for a white tee. It pairs with almost everything and creates a clean, effortless look. Neutral colors like black, gray, navy, and cream are also great staples.
Try it with: Blue jeans, trousers, cargos, sneakers, a hat and a watch.
The Button-Up
A button-up shirt instantly adds style without looking overly formal. This is where you can start experimenting with textures, fabrics, patterns, and colors.
Oxford shirts, linen shirts, camp collar shirts, and textured button-ups all create a relaxed but put-together look. Wear it buttoned up for a polished vibe or leave it open over a tee for something more casual.
Try it with: Trousers, jeans, loafers, boots, or clean sneakers.
The Polo
The polo sits perfectly between casual and dressy. It is one of the easiest pieces to wear when you want to look mature and intentional without feeling overdressed.
A fitted knit polo can look sharp for a date night, while a relaxed cotton polo works great for daytime events.
Try it with: Trousers, khakis, loafers, or white sneakers.
The Pullover
A good pullover adds warmth, texture, and style to an outfit. Crew neck sweaters and quarter-zips are versatile options that work in almost every season.
Layer one over a tee, polo, or button-up to instantly elevate your look.
Try it with: Jeans, trousers, boots, loafers, or sneakers.
BOTTOMS
The Blue Jean
Few pieces are as versatile as a good pair of blue jeans. They can be dressed up, dressed down, and worn nearly anywhere.
Experiment with different washes and fits to find what works best for your body type. Straight-leg and relaxed-fit jeans are timeless options that pair well with almost everything.
Style tip: Avoid overly distressed jeans for first dates. Clean, well-fitting denim always looks more polished.
The Trouser
Trousers create a sharp, tailored appearance while remaining comfortable. They instantly make an outfit feel more elevated and intentional.
The best part is their versatility. Pair them with loafers for a refined look or sneakers for a more casual, modern outfit.
Style tip: Neutral colors like black, gray, navy, olive, and beige will give you the most outfit options.
The Khaki or Cargo Pant
Khakis strike the perfect balance between casual and clean. They are a closet staple that works for everyday wear and can easily transition from day to night.
Modern cargo pants offer a similar versatility with a slightly more relaxed and contemporary feel.
Try it with: T-shirts, polos, button-ups, sneakers, boots, or clogs.
SHOES
Shoes can make or break an outfit. Even the best clothing choices can fall flat if paired with worn-out or mismatched footwear.
Sneakers
A clean sneaker is one of the most versatile shoes a man can own. White leather sneakers, retro runners, and minimalist styles work with almost everything.
Loafers
Loafers are perfect when you want to look polished without going full dress shoe. They pair especially well with trousers, polos, and button-ups.
Boots
Chelsea boots, work boots, and leather boots add structure and confidence to an outfit. They are particularly great during colder months.
Mules/Clogs
Birkenstocks and other clog-style shoes have become a modern staple. They offer comfort while still looking intentional when styled correctly.
ACCESSORIES
Accessories are where your personality gets to shine. They are small details that can make an outfit feel uniquely yours.
Hat
A hat can add character while also making an outfit feel more complete. Baseball caps, dad hats, and vintage-inspired styles are all great options.
Watch
A watch is timeless. It communicates attention to detail and can elevate even the simplest outfit.
Rings
Rings can add subtle personality and confidence. Start with one or two simple pieces and build from there.
Chain or Necklace
A chain is an easy way to add visual interest. Whether you prefer something minimal or more noticeable, jewelry can help express your personal style.
RECOMMENDED STORES TO SHOP at
Whether you're building a wardrobe from scratch or adding a few new staples, these stores offer great options for different styles and budgets.
Mix and match these pieces and you'll look your best every time.
Remember, style is personal. You should always express yourself however you want. Use this guide as inspiration, not a rulebook. The goal is not to dress like everyone else. The goal is to find what makes you feel confident.
The most attractive thing you can wear is confidence, and confidence often starts with feeling good in what you're wearing.
Find your style. Find your confidence. Maybe even find love.
Check out our upcoming speed dating events here and put your new wardrobe to good use.
Looking to make fun adult friends? Come to a Find Fun event or check out these friend groups in Indianapolis.
