The Most Comfortable, Functional Clothes I Own

I've recently gotten interested in comfortable fashion — fashion that feels great in addition to looking great. 

Here the the most comfortable, functional items in my wardrobe, all of are also extremely versatile. I'm talking casual and nicer outfits, and having the ability to get worn multiple times a week without getting sick of them.

Photography by Sam Murray

Photography by Sam Murray

1.  My timbs (Women's 6-inch Premium Waterproof Boot, $180 at Timberland.com) They feel good on my feet, the laces are strong and easy to tie, and they provide plenty of traction in the winter snow. I also love the way the look. No matter how popular these boots become, I don't think I'll get tired of their classic look. 

Gap Broken-In Straight Khakis aka boi pants, $49.95

Gap Broken-In Straight Khakis aka boi pants, $49.95

2. My multiple pairs of broken-in straight khakis from Gap ($49.95). I've slept in them before. They have a magical quality of suiting my gender identity while not chafing my thighs. See me modeling them here and here.

Everlane The Crew Sweatshirt, $40

Everlane The Crew Sweatshirt, $40

3. Everything I've ever owned from Everlane, but this sweatshirt in particular. I don't know what it is about this sweatshirt, but I want to wear it everyday. It's so soft, fits perfectly, and goes with everything. Esquire agrees it's the best sweatshirt ever.

Bass Men's Pomona Oxford, at Amazon for $67.15

4. Bass shoes. I just got these shoes from Bass, and I LOVE THEM. They feel so good on my feet and so good to walk in. My last pair from Bass lastly several years through many wears a week, so I feel good about the purchase.

5. My new Dakota watch. Dakota kindly sent me this fantastic watch, and I'll review it in full soon. But for now, here's a sneak peak I snagged after getting it sized and putting on on for the first time. It fits snug but not too tight, you can hardly hear the tick, and it goes with almost everything. I could also easily wear it to bed by mistake without thinking about it. 

6. My Topman Mid Wash Skinny Jeans* They're pretty soft and unlike most jeans, just feel like they're made for my bod. Also wearing them in the first picture with the Timberland boots.

So what do you think? Do you suffer for fashion, or do think there's always a more comfortable alternative? What are your favorites items? Post in the comments.

*Topman is sponsoring Qwear. Read about their sponsorship here.

As Qwear's Founding Editor, Sonny’s work centers around envisioning a future in which the clothing people wear does not dictate their chances of survival. Sonny was awarded 2015 dapperQ of the Year and was the first trans blogger to be sponsored by Topman. In March 2016, Sonny spoke at South by South West's first official queer fashion panel.