The saddle bags of the past were originally designed for military dispatch riders. They have that unmistakable crescent shape, which is actually quite feminine in my opinion. Along with today’s messenger bags, the newest saddle bags are a perfect example of a designer mixing form, function, tradition, and ingenuity

The cross-body bag has reigned supreme for the past few years, but they might need to move over a spot or two to make room for their lovely sisters!

Chloe Drew Small Shoulder Bag $1,950
Chloe Drew Small Shoulder Bag $1,950

The Chloe Drew bag has surpassed all other saddle bag designs in my mind. There are two different sizes, and neither are too small. This small version is quite literally the perfect size for a small bag. There are so many different variations and colours. Chloe nailed it!

Chloe Drew Small Shoulder Bag $1,850
Chloe Drew Small Shoulder Bag $1,850

The Drew in a lovely wine shade for Fall/Winter.

Chloe Drew Nano Floral Leather Saddle Bag $1,950 

Metal embellishments make this Drew a statement piece that is trendy, yet will stay a classic.

Chloe Drew Small Python Shoulder Bag $3,990 

Multi coloured python print is right on league with the past seasons lingering boho prints.

Chloe Marcie Mini Saddle Bag $750 

A little more minimalist than the Drew, this grey Marcie is a great everyday neutral.

Salvatore Ferragamo Rosette Small Saddle Crossbody Bag $1,290 

Overlapping pieces of leather on the flap give this one a modern and classy look.

Michael Kors Bedford Leather Crossbody $106 

This is such a great deal right now, I believe this colour is from the Spring collection.

Loeffler Randall Saddle Bag $395 

Classic black with the trendy new black hardware.

Henry Beguelin Molly Small Croc Stamped Messenger Bag $1,250 

Vintage croc.

Rebecca Minkoff Astor Laser Cut Leather Saddle Bag $295 

I have been seeing a ton of laser cuts in bags lately. Tory Burch did some lovely ones this past Spring and Summer. The laser cutting does tend to have a warmer weather vibe to it, but this bag proves the trend can go either way.

Tom Ford Jennifer Medium Leather Saddle Bag $1,990 

Tom Ford, need more words be spoken?

Tory Burch Embroidered Medium Saddle Bag $795 

There is certainly still a western vibe to some of the latest Fall and Winter collections. Tons of suede, fringe, and crops of riding boots. This Tory bag would go nicely with suede.

Tory Burch Frances Leather Saddle Bag $450 

This is a slightly pebbled leather, and I love Tory’s pebbled leathers. They are soft and well made. The tassel gives this one just enough flair!

Have you jumped in the saddle bag yet?