Woodbine Fashion on a Budget

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The Woodbine Mile Stakes isn’t just the most iconic race of the Toronto, Ontario track’s season, it’s also the beginning of something every stylista loves: fall fashion season! Autumn is one of my favorite seasons for creating looks, since there’s so much diversity in what you can wear: dresses, skirts, and pants are all in play; and, accessories like knee-high boots, tights and scarves come back to help enhance every look.
In honor of the Ricoh Woodbine Mile on Sept. 14, here are five looks (and one bonus barn-appropriate ensemble!) that you can rock that won’t break the bank.

14WoMile01 by penelopemiller featuring a woven dress
I love the autumnal orange of the dress at this look’s center – and, at only $30 from BooHoo, I love its price, too! I’m also obsessed with the faux leather motorcycle jacket, which rings up at $40 from Amazon.com; and you can add a killer pashmina (plus, it’s reversible – yay!) for $12 to your cart (also via Amazon.) The $40 handbag is from Rampage, and the suede booties are $44 from Bandolino. Finish off your outfit with an of-the-moment ear cuff at $40 from Mango and your entire ensemble is just $206.

14WoMile02 by penelopemiller featuring faux suede booties
Another reason to love the fall? Plaid is back! I love the subtly punk influence that plaid lends and outfit, and this pair from Front Row Shop is just $35. I added a $21 “Boyfriend” blazer from J. Tomson, a $30 cap-sleeve French Connection shell and a pair of saturated burgundy-tone booties for $37 by Fergie. Add a chunky statement necklace for $20 from 7TwentyFour, a major ring ($8.90, Windsor Store) and a studded handbag by Go Jane for $48. Finish it all off with a coat or two of Essie nail polish ($8.50) in Dressed to Kilt and you’re ready for the Woodbine Mile for just $208.40!

14WoMile03 by penelopemiller featuring no sleeve shirts
I built the whole next look around the awesome pair of spectator-style pumps I found from Michael Antonio for $74; I love the cobalt and silver accents, and I added a high-waisted houndstooth retro-inspired skirt for just $20 from Style Moi. Add a cobalt blue shell for $50 from Uniqlo (tucked in, please!), a $28 tank watch from Casio and a $38 black leatherette handbag from Yoyo Melody; toss on some red lipstick for $6 from NYX for a bolder look. Your final touch is a feather and floral hair clip from Accessorize for just $23, and you’re raceday-ready for $239.

14WoMile04 by penelopemiller featuring two-tone pumps
You can never go wrong with a little black dress, and I love this $44 version from BooHoo. I added a fascinator ($40, Amazon.com) and a standout pair of patterned pumps for $45 from Bumper. A black, patent-leather purse for $45 from Mango and a delicate necklace for $19 from Natasha Accessories keep this look chic and affordable for a grand total of $193.

14WoMile05 by penelopemiller featuring a blue purse
Our last look is both flirty and fabulous for a day at the races. The miniskirt is from BooHoo (I seem to really like that store this fall!) and is $20; I paired it with a $8.99 J. Tomson long-sleeve shirt, a $28 Leslie Danzis multi-strand necklace, and Naughty Monkey’s knee-high suede cowboy boots for $100. Add a $40 Urban Expressions clutch that pulls its color from the skirt’s details and a $20 Charlotte Russe watch and you’re ready for the races for just $216.99. Score!
Bonus: If you’re in the mood to go to the track in the morning and watch horses train, bear in mind that it may be a little chilly on the Toronto mornings. Here’s an easy look to put together that will keep you both stylish and comfortable as you witness the sheer beauty of mornings at Woodbine.

14WoMile06 by penelopemiller featuring black shoes
I’m probably going to head to Express and pick up these $48 jeans – they look incredibly comfy. I added a cableknit sweater for $16 from Forever21, a pair of Chucks for $50, a $50 Columbia fleece vest and a $24 ombré knit cap from Leith. Throw your camera into this slouchy $50 purse and you’ve got a versatile look for a morning at the barn for $238 total.