A GENTLEMAN'S GUIDE TO KENTUCKY DERBY FASHION: FIRST-TIMER'S EDITION

updated on 16 February 2025

Just got invited to the Derby and starting from scratch with dress clothes? Don't worry - dressing for Derby Day isn't as complicated as it might seem. Here's what you need to know.

The Basic Approach

You have two solid options. The simpler route is a sport coat with dress pants - think spring colors like light blue, pale yellow, or soft pink jackets paired with crisp white or tan pants. The second option is a full suit in similar cheerful tones. Either way, you'll want something that feels right for a May afternoon in Kentucky.

What You'll Need

- Sport coat or suit that fits well (a good store will help with this)

- Light-colored dress shirt (white is foolproof)

- Tie or bow tie in spring patterns or colors

- Pocket square (doesn't have to match anything exactly)

- Comfortable dress shoes (you'll do lots of walking)

- A hat if you'd like (plenty of guys go without)

Colors to Consider

The Derby is about embracing spring colors. If this is your first sport coat or suit purchase, consider:

- Light blue

- Soft pink

- Pale yellow

- Mint green

- Light tan

- Subtle pastel patterns

Getting the Right Fit

This might be your first time buying dress clothes, and that's fine. The key is working with someone who can help you get the right fit. A well-fitted jacket shows better than an expensive but ill-fitting option.

When to Start Shopping

Give yourself some time with this. You'll want to try things on, and if anything needs alterations, that takes extra time. Our directory includes shops and clothiers who are used to helping guys who are just starting to build their dress wardrobe.

When you need to what to wear to the Kentucky Derby, our directory  connects you with quality men's clothing shops to get ready for the Kentucky Derby. Many of them regularly help first-time Derby attendees find exactly what they need.

Find your men's clothing store to get started and get ready for the Derby: https://www.hollowayandhare.com/derby-mens-clothiers/ 

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