Outfits of the Month (3): The Classic Flat Cap Styled for Winter
Wednesday January 14, 2026

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About 15 years ago, wanting to find hats to add style, but also because hats are great but you just don’t see them worn in the states that often, I purchased two wool flat caps (black and taupe). I still wear them every winter when the temperatures dance just above freezing and they keep my head perfectly warm while also adding a touch of style.

Since that time, and with my travels to Europe, I have added Panana hats to my summer wardrobe and again am reminded that hats can have style as well as functionality. Baseball caps are not the only option, nor are stocking caps in the winter. Thank goodness! Don’t get me wrong, I love and will regularly reach for my cloth baseball caps when I go walking during spring and summer and pay attention to the color, but there is an elevation to the entire wardrobe when a flat cap (another great option depending on one’s face shape is a newsboy’s hat), panama or fedora is chosen.

Yet another detail we can add to our wardrobe to finish it while also adding a touch of signature style.

Upon reflection, part of the reason I didn’t wear such hats as often in the distant past is that I didn’t see many people wearing hats, and you really do make yourself noticed when you wear a stylish choice for the head, especially when others are forgoing this option even if it would make sense to do so to either protect our face from the sun or keep our head warm. I finally cast that fear of what others might think aside, and have been wearing my hats with frequency both in winter and summer. What a joyful choice, and no sunburn or chill!

Recently, in a Financial Times article, they shared how these caps are coming back in style with the younger generation, and what great news. However, what this article also demonstrates is that this style choice is timeless. All the more reason to purchase one (or two) for your wardrobe needs and color preferences and purchase well. In this month’s post, I will be styling outfits with the flat cap, introducing you to British and Irish brands (and one Boston brand) that make them so that you can explore all of the many designs, colors and fabrics they offer because there are many and what you will see below is just a small sampling.

Let’s get to the outfits!

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~Borges & Scott’s The Woods – Yorkshire Tweed Flat Cap (many colors)~

~AllSaints Ara East West Suede Tote, two colors, cognac or steel blue (shown)~

~We Norwegians Setesdal merino wool and cashmere vest, navy, 50% off~

~Joseph’s Joe Silk Crepe de Chine Blouse~

~Sofft’s Paige Chelsea boots, brown~

~Frame’s Mellow wide-leg jean in Solace wash, 27.5″ inseam~

~How Great Ideas Happen: The Hidden Steps Behind Breakthrough Success by George Newman, to be released on Janaury 27th~

~SHOP THE OUTFIT:

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~Gaelsong’s Ladies Irish Linen flat cap, many colors~

~Veronica Beard Aaliyah striped cotton-blend blazer, two colors, 55% off OR Evereve’s Rory Multi-Stripe Blazer~

~Veronica Beard Lisa 70mm Pointed Toe bootie, many colors~

~Vince’s Double Face Check Wool & Cashmere Scarf~

~Frame’s The Vertical jean, in Brazen wash, 32.5″ inseam~

~The Typewriter and the Guillotine: An American Journalist, a German Serial Killer, and Paris on the Eve of WWII by Mark Braude, to be released on January 20th~

~SHOP THE OUTFIT:

Untitled design

~Boston Scally Co., The Winter Rose, – frozen plaid (scally cap, similar to a flat cap)~

~Stuart, Stuart Weitzman Power 85 Pump, nice blue, other colors available~

~Mulberry’s Small Darley Leather Crossbody Bag~

~Loewe’s classic rounded soft belt, many colors~

~Avec Les Filles Belted Longline Trench Coat~

~Lily Silk’s Sprezzatura Silk Blouse~

~Quince Ultra-Stretch Ponte Trouser, navy (black and burgundy also available), 30″ inseam~

~How to Be a Rich Old Lady: Your Guide to Easy Investing, Building Wealth, and Creating the Wild, Beautiful Life You Want by Amanda Holden~

~SHOP THE OUTFIT:

~Explore more Outfits of the Month posts here in TSLL’s Archives.

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12 thoughts on “Outfits of the Month (3): The Classic Flat Cap Styled for Winter

  1. I bought my first pair of jeans since the last 20 years, last week. I followed your advices since reading the blog and I am so glad that I found a pair that fit me well almost immediately instead of trying on so many until despair. Thank you. Now, my quest is on a great belt. I will also consider your posts for this.

    1. Véronique! So tickled to hear! Thank you for sharing. A quality belt is on my list as well, and I am going to invest. Loewe and Altuzarra offer great classic, yet well made belts, and then be sure to check Bergdorf’s for an array of styles from trusted brands. A simple, yet beautiful buckle ‘cinches’ the deal and while quietly, does finish the look to the eye. You’ve got this! 🙂

  2. I’ve been wearing hats off and on for years. But about 6 years ago, I decided to wear them year-round, when I’d be outside. With my complexion and my head shape, I really cannot wear ball caps or anything similar. Instead I wear fedoras, wool in the cooler months, straw in the warmer ones, and they are often men’s hats. I have received many compliments on them, even though few other people I see few people wearing them. And, I intend to continue wearing them.

    1. That’s awesome OreMoss! I am right there with you – keep on wearing them. You’ve found what works for you and that you like! That is the magic combo, isn’t it? 🙂 Thank you for sharing this.

  3. Love hats. I have both a brown and a charcoal tweed flat cap which get much used during our cooler months and, as much as I wish to wear them–so easy!–, I look just odd in a baseball cap. For the summer I have a variety of straw boaters, broad brims, and a fabric one with mesh inserts for gardening.Sofft’s Chelsea boots will last you forever, they are so comfortable and well-made, mine I think are 15 or so years old? Now of course, they look quite artistic & bohemian, shall we say, and so I have others for posher wear. Speaking of–I highly recommend Thursday Boot Company, both my husband and I have a few pairs of their shoes and boots. They are beautifully made and available in several styles.
    Belts! That is the top purchase on my new list! Many thanks for the reminder about Bergdorf’s and I’ll be perusing Nordstrom, JCrew, Quince, the usual suspects. Many thanks for all the ideas, Shannon!

    1. Thank you for recommending Thursday Boot Company! That is wonderful to know. 🙂 And couldn’t agree more about Sofft’s. Thank you for sharing your experience with this brand. Loved learning about thet hats you wear and love. 🙂 Picturing you looking very warm and chic in your flat cap. 🙂

  4. It’s so much fun to hear about more of the deeply shared loves of this special community…yes to hats! I mostly wear straw hats in summer sun or baseball caps whenever. My hair seems to render only a few styles carefree. I should look for a tweed or wool baseball cap, as I can always fit that with a pony tail! Love the flat caps here. Have a great week and long weekend if here in US. -Liz

    1. Thank you Liz! Yes, the flat cap makes it very functional for those of us who wear ponytails. 🙂 And as the article reminds, and I have to remember to not forget – always wearing the cap a little bit ‘off perfect’ or ‘put a bit of mustard’ a phrase I only learned from the article – love it already. 🙂

  5. I love the idea of hats as part of a unique style but I confess I’m stumped about how to figure out what hats work best for me. I have a larger head (m/l vs s/m) and am a bit self-conscious. Ball caps and beanies (carefully chosen to be thick enough) work. Any advice on how to select other types of hats? Thank you!

    1. Great question and you are not alone. It took me time as well. I have a big head for women’s sizes. The key is to make sure you get the circumference of your head and then the size that works for you. And then the brim needs to be proportionate to your head and face. Of course, based on the look you are going for, it should frame your features that you want to spotlight. Think, eyes, cheekbones, etc. I always choose a wider brim on my Panama hat for proportions compared to the standard brim length, and with my oblong face, a flat cap is more flattering than a newsboy hat which is looser and larger with more fabric.

      Whenever you are in a place where there are hats, take some time to try them on and look at yourself at all angles. I did this for a while and that helped immensely because we each have a unique face and then our own preference.

      If you like baseball caps, I think you would like a flat cap as it provides the front brim and a slim design. Now it is just up to you which color or pattern to choose!

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