Heloise | Penny Strap Loafers for Women
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These penny strap loafers combine a classic slip-on silhouette with a colorblocked design that mixes tones for visual interest. The loafers sit low on your foot with a rounded toe and feature a leather strap across the vamp—the signature penny slot detail that gives this shoe its name. A wooden heel keeps the profile grounded and preppy, while the structured construction means they hold their shape well. Wear them to work, casual outings, or anywhere you want a polished but relaxed look.
Key Features
- Penny Strap Detail: A wide leather strap crosses the vamp with a slot at the center, giving you that timeless loafer look that works with both casual and dressed-up outfits.
- Colorblock Design: Contrasting tones across the shoe add dimension and make the silhouette feel more modern and interesting than a solid pair.
- Wooden Heel: A stacked wooden heel gives you subtle height and a classic preppy vibe that pairs well with trousers, skirts, and dresses.
- Everyday Casual: Ideal for work days, weekend errands, or anytime you want a shoe that looks put-together without requiring much thought.
Use the fit finder next to the size selector for a recommendation in a few seconds, or see the full measurement charts below.
Every product page has a fit finder next to the size selector — three questions, one recommendation, a few seconds. These charts are for anyone who would rather read the numbers.
How to measure
- Bust / chest. Around the fullest part, tape level, arms relaxed at your sides.
- Waist. Around the narrowest part of your torso, usually just above the navel.
- Hips. Around the fullest part, roughly 8 in below the waist.
- Inseam. From the crotch seam to the floor, in the shoes you'll wear the trousers with.
Measure over the underwear you'd normally wear, not over clothing. Keep the tape snug but not tight.
Women's clothing
| Size | US | Bust (in) | Waist (in) | Hips (in) |
|---|---|---|---|---|
| XXS | 0–2 | 31–32 | 24–25 | 34–35 |
| XS | 2–4 | 33–34 | 26–27 | 36–37 |
| S | 4–6 | 35–36 | 28–29 | 38–39 |
| M | 8–10 | 37–38½ | 30–31½ | 40–41½ |
| L | 12–14 | 39½–41 | 32½–34 | 42½–44 |
| XL | 16–18 | 42–44 | 35–37 | 45–47 |
| XXL | 20–22 | 45–47 | 38–40 | 48–50 |
Men's clothing
| Size | Chest (in) | Waist (in) | Neck (in) |
|---|---|---|---|
| XS | 33–35 | 27–29 | 14–14½ |
| S | 36–38 | 30–32 | 15–15½ |
| M | 39–41 | 33–35 | 15½–16 |
| L | 42–44 | 36–38 | 16½–17 |
| XL | 45–47 | 39–41 | 17½–18 |
| XXL | 48–50 | 42–44 | 18½–19 |
Women's shoes
| US | EU | UK | Foot length (in) |
|---|---|---|---|
| 5 | 35 | 2½ | 8⅝ |
| 6 | 36 | 3½ | 8⅞ |
| 7 | 37–38 | 4½ | 9¼ |
| 8 | 38–39 | 5½ | 9½ |
| 9 | 39–40 | 6½ | 9⅞ |
| 10 | 41 | 7½ | 10¼ |
| 11 | 42 | 8½ | 10½ |
Men's shoes
| US | EU | UK | Foot length (in) |
|---|---|---|---|
| 7 | 40 | 6 | 9⅝ |
| 8 | 41 | 7 | 9⅞ |
| 9 | 42 | 8 | 10¼ |
| 10 | 43 | 9 | 10⅝ |
| 11 | 44 | 10 | 10⅞ |
| 12 | 45 | 11 | 11¼ |
| 13 | 46 | 12 | 11½ |
How our pieces are cut
- Dresses are cut true to size. If you are between sizes, take the smaller one — most of our dresses have ease through the waist.
- Coats and jackets are cut with room for a knit underneath. Take your usual size; size up only if you layer heavily.
- Knitwear is relaxed by design. Between sizes, take the smaller one unless you want an oversized look.
- Trousers and jeans run true to size. Between sizes, take the larger one.
- Shoes run true to size. If you have a wide foot, take half a size up.
Still not sure?
Write to info@halstead.com with your usual size, your height and the piece you're looking at. We'll tell you what we would pick — usually within a few hours. We would far rather get it right the first time than process a return.
We work in natural fibres — wool, cashmere, cotton, linen and full-grain leather.
Knitwear: cold hand wash or a wool cycle at 30 °C, no softener, dried flat and stored folded.
Coats: dry clean once or twice a season, stored on a broad wooden hanger.
Leather: wipe with a damp cloth, condition twice a year, never dry near heat.
Full guidance is on our Materials & Care page.
Shipping is free on every order to all 50 states, with no minimum.
Processing: 2–4 business days, while your order is picked and checked by hand.
Transit: 3–4 business days.
Total: 6–9 business days, with tracking emailed the moment it leaves Chesapeake.
Returns: 90 days from delivery. We email you a printable label; return shipping is deducted from the refund unless the fault is ours, and your first exchange is always free.