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All photography by Kim Baker

All brunch’s are off this Saturday as The Kentucky Derby is here again to fill your mimosas with mint juleps and pockets with possible winnings. This horse racing event is an opportunity to not only bet on a few races but the best time of the year for matching a pinstriped vest with a paisley pocket square. Whether you have the chance to go to the real event or just plan on going downtown for a celebratory afternoon, pairing the perfect pieces for a Derby Day outfit can be just as fun as the race to and from the bar. Luckily, you don’t have to go far to find it.

Sully & Co, a menswear boutique in Jefferson Park, offers a wide variety of high-quality, American-made pieces for any man who appreciates well-tailored, unique clothing. We got together with the owner, Mark and his wife to pull together five looks that are perfect for any Derby Day party and also great staples in yours or his closet.

5 Sully & Co. Inspired Looks For Derby Day

Outfit 1: Linen Denim

Outfit1If you’re interested in spicing up the material of your sports jacket for spring, a breezy linen style is a great option this time of year. For an even more stand out look, adding a gingham shirt or other fun pattern will give any outfit an edge and possibly a bit of luck on the betting front. It’s easy to stick with a tie but opting for a bow tie instead can be the cherry on top of an already distinct Derby ready look. Sully & Co. offers a wide variety of prints and patterns for all color palettes and any gentleman who desires a down-right dapper outfit.

Outfit 2: Seersucker Savvy

outfit2There’s a reason seersucker has been around for so long and it’s easy to pull off with the right fit and length. Let the seer stand out by combining it with a pop of color pocket square and a tie that will bring envy to all who decided to go without. The attention to detail is all you need to make this look ready for a day packed full of people dressed in their best. Plus, you can’t go wrong with a pinstriped pant.

Outfit 3: Birds and Burgundy

outfit3Putting a bird on it goes a long way with a subtle piece that has a lot of character. Combining a burgundy sack jacket with a stand out tie is the perfect way to balance separates that go even better together. Each piece is designed to compliment your look but also stand out on its own. It’s time to celebrate and picking out the right pattern that fits your style is just as important as that bourbon you’re probably going to have more than one of.

Outfit 4: Patterns on Patterns

outfit4Changing out a pair of sunglasses for a tie is another great way to keep it classy all day. Pick out your favorite pattern and mix it up with multiple colors with your shirt and jacket, adding a stand out square to compliment the entire look. Lighter colors are great for the warmer weather and will leave your feeling festive with just the right amount of suave.

Outfit 5: Pinstripe Party

unnamed[1]It’s easy to go all out for the Derby with anything and everything pinstriped. A dark blue works wonders for any vest and trouser combination, especially with the right tie and drink pairing. However, if you’re down with the vest but prefer a more casual bottom, a fun color is another great way to pull the vest together. You don’t have to match everything to make it work but keeping it to 3-4 colors is the best way to look put together but not over the top.

It’s time to retire your Sunday best and make room for pieces that will make any man feel like Don Draper. Get creative with your Derby Day style while still being able to invest in long lasting pieces for many events to come. There aren’t many things more American than the Kentucky Derby so what better way is there to honor such an event than in your best American-made apparel? 

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