A Romantic Visit to Keeneland: What to Wear to the September Yearling Sale

Whether you are visiting Keeneland's September Yearling Sale to spend a romantic fall day enjoying the beauty of the horse track... or you are planning on purchasing a horse... here are some suggestions for what to wear to this romantic and picturesque event!

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Lady's Fashion

From our observations, shoes are the most important element of a sale outfit! Sneakers are the most functional and common option, however when the weather is nice, comfortable sandals can also be a good choice. Check out our favorites below!

• Golden Goose

Definitely not for everyone in both aesthetic and price point... but are totally the vibe of the September Sale at Keeneland. Check out the official website or try a cheaper version from amazon!

• Cloud-Style Sneakers

Comfort is a priority for many patrons of the sale as they are attending for a full day of business. We suggest the ON brand or Hokas. They are both trendy at the moment... but have a very different style statement. ON brand can be found here. And a great Hoka option can be located here!

• Style Sneakers

Any sneaker that can be styled with jeans or with leggings is going to be a good choice. Personally, we think the Veja sneaker is so versatile and perfect for any event. We also saw other brands like Nike, Adidas, and New Balance.

Best Tip: We definitely recommend selecting something that your foot feels comfortable in (in case you want to go on a more extensive exploration of the grounds) and something that makes you feel like yourself!

In terms of outfits, there is a large variety. Most people went for jeans, sweaters, and vests (layering is a must during the unpredictable weather of September)... however there were some nicer selections like flow-y tops and dresses. If you want to really go all the way... we suggest adding a tasteful straw hat to your look!

• Jeans

We saw lots of skinny jeans... yes! Skinny jeans! Mostly without any holes. We are guessing they are still popular at Keeneland during the yearling sale because of how mimic the style of riding pants... let us know if you have any other theories! Try something like this!

• Layers!

Incorporating layers is a must if you plan to stick around the sale for a few hours... from walking between the exterior and interior venue sites... to unpredictable weather... it is best to add a vest (like this one) to your outfit.

• Add a hat

While a hat might not go with every outfit... don't be scared about styling a look around different hat selections. from an athletic ball cap to a useful small brim straw hat... this event is the perfect place to try something new!

Best Tip: There are so many different people who attend the Keeneland September Yearling Sale... for different reasons and with different outfits. The best thing we can recommend to wear is something you feel confident in!

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Gentlemen's Fashion

We recommend starting with shoes when selecting an outfit. This can help direct you towards a cohesive look (either athletic or more sleek). Check out our suggestions below!

• Cloud-Style Sneakers

Comfort seems to be a trend for feet at the moment! We noticed many attendees wearing cloud style sneakers like the ON brand or Hoka shoes. These shoes are very different in feeling and style... make sure to prioritize something that works for you!

• Style Sneakers

Sneakers with personality are always a good choice in our opinion. We love how different sneakers can bring out and showcase individuality creatively. Here are some of out favorite finds on amazon: check out these colorful shoes or this neutral option.

• Dress Shoe

If you are wanting a more classic look... dress shoes are always an option! Currently, styles are more athletic even in dress shoes which is why we like this option for a fancier outfit!

Best Tip: When selecting a shoe... we recommend considering the surfaces you plan to walk on... there will be interior and exterior pathways open for exploration... but there are also sidewalks that are shared with horses... be aware of your footing!

There are so many options when it comes to outfits! From full on athleisure to something more professional, there is surprisingly a lot of overlap between what we saw in men's and women's outfit selection.

• Pairings

We saw plenty of outfits with jeans (or nice shorts). Most people opted to pair these pants with a plaid button up and a vest... but there was a variety of other combinations with sweatshirts or sweaters.

• Add a hat

Things are a bit easier for the men... but something we did notice was that almost every man was wearing a hat with his outfit... regardless of fanciness! We recommend going for something more simple in design... like this!

Best Tip: Keeneland in known for its dark green color... from logos, to staff uniforms... and even to their cars... Keeneland likes to use dark green. We recommend staying away from this color in your outfit so you don't blend into your surroundings too much. Or you don't get confused for a staff member!

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Final Thoughts...

So, there you have it! Our observations and recommendations for what to wear when attending the Keeneland September Yearling Sale! We love this event and have made some lovely memories while attending... so we definitely recommend other couples check it out No matter what outfit you select, we hope you have a truly magical experience together.

With love,

Romantic Lexington