Hey Prepsters,

Great style isn’t about having a million things that cost a million dollars, it is about what you able to do with what you have. For this post, I am sharing how I styled a pair of flannel trousers from Banana Republic, three different ways.

I tried to keep each look with a good combination of high-low pieces, as that’s pretty much a good representation of how I actually dress on a regular basis… and too be honest, I feel like the most of us dress like that as well. Additionally, I always think of three different looks that I can wear an item with before buying it, which is a great general rule of thumb. Without further ado, here my 3 looks!

Look 1. Dark & Modern


For the first look, I wanted to showcase this beautiful wool jacket with a faux shearling collar, from H&M! I found this piece at H&M for $30 on sale and instantly knew that I would be able to wear it over and over (sometimes a guy gets lucky). This look is quiet dark, but simple and elegant. The pant is a dark navy flannel, but has almost an appearance of being black. Which is why I paired with a simple grey Ralph Lauren turtleneck, the black H&M jacket, and black Le Chateau chelsea boots. To complete the look, I went with my matte black Tom Ford sunglasses. Rough total cost – $700

Look 2. Preppy & Warm


The second look is my personal favourite, simply because I am obsessed with my Faconnable cashmere-wool cable knit cardigan! I found this piece at Winners’ for $79 from $1200. It had a little tear on the back, so the store was kind enough to lower the price to $60 to accommodate the cost of taking it to a tailor. All together, with tailoring, this piece came in at just over $72… for a total saving of $1128! I added warmth to the look with a Burgundy and navy plaid shirt and a burgundy scarf, both from Joe Fresh. I tied in the burgundy with my Cole Haan monk straps and a Cole Haan pouch. To complete the look I added a hint of gold with my sunglasses from Ray Ban and wore a Brathwait watch. Rough total cost $1000.

Look 3. 50 Shades of Grey!


For the final look, I went for a very textured, but monochromatic look. I loved the idea of layering this knit oversized RW&CO cardigan over a Ralph Lauren houndstooth blazer. So it was turtleneck, blazer, cardigan (very darn warm). Once again I wore my black chelsea boots. To complete the look, I accessorized with my Caravelle NY gunmetal + tortoiseshell watch and matte tortoiseshell sunglasses by TOD’s. Rough total cost $1300

I hope you guys are feeling inspired to wear your favourite pieces in multiple different ways! This was so much fun to shoot, and I am so happy to be back with a ton more content! Thank you for reading! Be sure to follow myself on social @ThePrepGuy

Photography: @ThePhotoGuyy


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  1. Love the shades of grey look the most!

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