How to Wear (Feminine) Menswear

Suit up for work (or weekend) with creative layers and proportion play! This season, we’re all about borrowing style tips from the boys without sacrificing femininity. By adding simple pieces like tailored blazers, textured basics & tucked-in tops, you can create a look that’s polished & sophisticated. Check out 3 timeless looks below!


How to Get a Downtown Dapper Look

Cropped pants are a refreshing update to a work pant & blazer match-up. We love how the structured jacket balances out the looser fit of culotte trousers. If culottes aren’t quite your thing, try this look with cropped chino instead.

Stylist Tip: You can pair navy & black together! For an on-season approach, incorporate other fall neutrals—like burgundy & cream—to pull the ensemble together.


How to Wear Tailored Layers

For a look that’s nonchalant yet still polished, try wearing your white button-up all the way buttoned. Layer the look with a denim jacket and a knotted lightweight scarf for a take on the ascot. Polish off your outfit with an oversized blazer and patent-leather loafers.


How to Skirt the Style Rules

Go structured prep with dapper details like leather elbow patches & classic loafers—they’re timeless. Pair them with an A-line skirt in a vintage-inspired print (or texture like tweed or houndstooth) to add a touch of femininity. If it’s a chilly day, throw on a pair of tights! Don’t be afraid to play with tights that are textured or in a fall color like burgundy or olive.

Stylist Tip: Cuff, cuff and away! Roll up the sleeves of your shirt and jacket(s) to show off your layers and any contrasting lining.

Is it time to add a few menswear-inspired outfits to the rotation? Our style experts are ready to lend a hand. Take your style quiz, order a Fix and let your stylist know you’d like to add classic button-down shirts, tailored blazers and polished and professional staples to your wardrobe. Or, head over to Stitch Fix Freestyle™  to instantly buy feminine menswear curated just for you. Sit back and relax while everything comes to your doorstep. Shipping, returns and exchanges are always free. 

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