The Winter Look Book

Welcome to the Philly Gents Winter Look Book! Winter is here so let’s face it with a proper wardrobe.

In this gent’s opinion, winter attire has the most charm out of all of the seasons. There’s just something comforting about rich wool and denim fabrics that make us feel cozy. And textures like herringbone, fleck wool and dogstooth have such a charming and warm aesthetic to them.

The winter wardrobe is also practical and literal. With the weather being so unpredictable, we rely on hearty textures, rich fabrics and layering in order to brave the elements. And for color schemes, we are looking at dark and cold shades, which is quite fitting considering our environment!

At a high level

  • Featured items in this edit:
    • Fabrics: wool, denim
    • Colors: navy, charcoal, brown, khaki, burgundy
    • Clothing: overcoats, vests, blazers, turtleneck/roll neck sweaters
    • Accessories: hats and gloves
  • Featured brands:
    • ASOS
    • Suitsupply
    • Topman
    • Zara

I have provided six outfits below along with links so you can shop the look. Hopefully this guide helps give you some ideas now that the holiday season is over and winter has set in. Plus, there are plenty of sales popping up on our favorite sites and this is the perfect time to snag some deals!

Blazers and suit jackets

A hearty wool blazer is a winter staple for the modern gent and there are so many varieties to pick from! My favorite is a good wool fleck or herringbone pattern but any rich-looking texture will do.

Sadly, a few of the items featured above have run out of stock (thanks, Holiday clearance sales!) but I have offered lots of alternates below. Fortunately, the Heart & Dagger dogstooth fleck jacket featured in look #5 is still available, although barely. Although not 100% pure wool, this wool blend feels great and drapes well. It also has some elastane for stretch and comes at a great price point. If you’re looking for pure wool all the way, go with Suitsupply or Bonobos, known for their amazing fabrics.

Sweaters, shirts and vests

Vests are a fun addition in the layering rotation and they can be paired with shirts and sweaters alike. And in the name of protecting our necks, rollneck or “turtleneck” sweaters are back in season.

The blue denim chambray shirt I am wearing in looks #1 and #6 was custom made through Proper Cloth. If you are looking for an office-friendly denim shirt, you can design and order your own through Proper Cloth or grab one at Suitsupply. More casual denim chambray options can be found at ASOS and Zara.

Overcoats & Outerwear

The overcoat will be your go-to because it pairs perfectly with a suit but is also versatile enough to work with casual looks. Plus, it’s a timeless classic that will never go out of style. The fit should be slim but with enough room for a blazer or jacket to fit snugly underneath.

As far as trends, shearling is in, as are rugged-looking outdoorsy coats. The shearling coat from look #4 (super warm, btw) is *almost* out of stock at Zara, but Topman and Nordstrom have several awesome alternatives.

Boots and shoes

You can’t go through a northeast winter without breaking out the winter boots. Fortunately there are lots of dressy options available for your feet that are nice enough for the office (or a date) while still protecting your feet (and your dress shoes at home!) from the elements.

Of course, boots are not as comfortable and free-moving as traditional shoes, so you can’t wear them every day. That’s why you’ll be relying on dress shoes and sneakers on the drier winter days. Dress sneakers like the Santoni’s I have featured are a year-round shoe but a nice chocolate brown tone makes for a perfect pairing for the dark shades in your winter outfits.


Last on the list are a few accessories that enhance the game. I wouldn’t say they are a staple but they are the icing on the metaphorical cake. The infamous gloves I feature in looks #3-6 are none other than the Polo Ralph Lauren and can be found year after year at Nordstrom. Although I won’t be sporting a scarf now that I have the beard (wool damages the hair follicles!), I have a few favorites I can recommend.

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